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  • 3382-18-1 Structure
  • Basic information

    1. Product Name: 6,7-Dimethoxy-3,4-dihydroisoquinoline
    2. Synonyms: 3,4-dihydro-6,7-dimethoxyisoquinoline;6,7-Dimethoxy-3,4-dihydroisoquinoline;Isoquinoline,3,4-dihydro-6,7-dimethoxy-
    3. CAS NO:3382-18-1
    4. Molecular Formula: C11H13NO2
    5. Molecular Weight: 191.23
    6. EINECS: 222-185-9
    7. Product Categories: Drug Intermediates
    8. Mol File: 3382-18-1.mol
    9. Article Data: 70
  • Chemical Properties

    1. Melting Point: 39-40℃
    2. Boiling Point: 155-161℃/1mm
    3. Flash Point: 121.99 °C
    4. Appearance: Yellow/Low Melting Solid
    5. Density: 1.134 g/cm3
    6. Refractive Index: 1.5930
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: 6,7-Dimethoxy-3,4-dihydroisoquinoline(CAS DataBase Reference)
    10. NIST Chemistry Reference: 6,7-Dimethoxy-3,4-dihydroisoquinoline(3382-18-1)
    11. EPA Substance Registry System: 6,7-Dimethoxy-3,4-dihydroisoquinoline(3382-18-1)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 3382-18-1(Hazardous Substances Data)

3382-18-1 Usage

Chemical Properties

White powder

Check Digit Verification of cas no

The CAS Registry Mumber 3382-18-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,3,8 and 2 respectively; the second part has 2 digits, 1 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 3382-18:
(6*3)+(5*3)+(4*8)+(3*2)+(2*1)+(1*8)=81
81 % 10 = 1
So 3382-18-1 is a valid CAS Registry Number.
InChI:InChI=1/C11H13NO2/c1-13-10-5-8-3-4-12-7-9(8)6-11(10)14-2/h5-7H,3-4H2,1-2H3

3382-18-1 Well-known Company Product Price

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  • Alfa Aesar

  • (H64018)  6,7-Dimethoxy-3,4-dihydroisoquinoline, 97%   

  • 3382-18-1

  • 250mg

  • 245.0CNY

  • Detail
  • Alfa Aesar

  • (H64018)  6,7-Dimethoxy-3,4-dihydroisoquinoline, 97%   

  • 3382-18-1

  • 1g

  • 735.0CNY

  • Detail
  • Alfa Aesar

  • (H64018)  6,7-Dimethoxy-3,4-dihydroisoquinoline, 97%   

  • 3382-18-1

  • 5g

  • 2940.0CNY

  • Detail

3382-18-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 6,7-Dimethoxy-3,4-dihydroisoquinoline

1.2 Other means of identification

Product number -
Other names 2,3-dihydro-5,6-dimethoxyisoquinoline

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:3382-18-1 SDS

3382-18-1Synthetic route

N-[2-(3,4-dimethoxyphenyl)ethyl]formamide
14301-36-1

N-[2-(3,4-dimethoxyphenyl)ethyl]formamide

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

Conditions
ConditionsYield
With phosphorus pentachloride In dichloromethane at 20℃; for 0.5h; Bischler-Napieralski Reaction; Inert atmosphere;100%
With trichlorophosphate In toluene89%
With trichlorophosphate In toluene at 85℃; for 1h; Bischler-Napieralski cyclization;76%
3,4-dihydro-6,7-dimethoxyisoquinoline hydrochloride
20232-39-7

3,4-dihydro-6,7-dimethoxyisoquinoline hydrochloride

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

Conditions
ConditionsYield
With sodium carbonate In water Inert atmosphere;99%
With potassium carbonate In diethyl ether; water4.12 g
6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
1745-07-9

6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

Conditions
ConditionsYield
With carbon dioxide; DBN; Eosin Y In dimethyl sulfoxide at 25 - 30℃; for 48h; Irradiation;97%
With tert.-butylhydroperoxide; tris(triphenylphosphine)ruthenium(II) chloride; palladium In decane Molecular sieve;96%
With 4-tert-butyl-5-methoxy-1,2-benzoquinone; oxygen In acetonitrile at 20℃; for 48h; Schlenk technique;95%
hexamethylenetetramine
100-97-0

hexamethylenetetramine

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

Conditions
ConditionsYield
With acetic acid; trifluoroacetic acid for 5h; Reflux;95%
With trifluoroacetic acid In acetic acid at 90℃; for 0.5h; Pictet-Spengler Synthesis; Inert atmosphere;94%
In acetic acid; trifluoroacetic acid for 0.5h; Pictet-Spengler reaction; Heating;90%
With acetic acid; trifluoroacetic acid at 90℃; for 0.5h; Inert atmosphere;90%
6,7-dimethoxy-3,4-dihydroisoquinoline perchlorate

6,7-dimethoxy-3,4-dihydroisoquinoline perchlorate

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

Conditions
ConditionsYield
With sodium hydroxide In water pH=10;92%
2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

formic acid ethyl ester
109-94-4

formic acid ethyl ester

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

Conditions
ConditionsYield
Stage #1: 2-(3,4-dimethoxyphenyl)-ethylamine; formic acid ethyl ester for 14h; Reflux;
Stage #2: With phosphorus pentachloride In dichloromethane at 20℃; for 2h;
90%
Stage #1: 2-(3,4-dimethoxyphenyl)-ethylamine; formic acid ethyl ester for 12h; Reflux;
Stage #2: With trichlorophosphate at 0 - 40℃; for 3.33333h; Bischler-Napieralski Reaction;
75%
N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

Conditions
ConditionsYield
Stage #1: N-methylhomoveratrylamine With formaldehyd; Eaton’s reagent at 85℃; for 2h; Inert atmosphere;
Stage #2: With sodium hydroxide In Isopropyl acetate; water at 25℃; pH=8-8.5; Concentration; Temperature;
84.23%
6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
1745-07-9

6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

A

6,7-dimethoxyisoquinoline
15248-39-2

6,7-dimethoxyisoquinoline

B

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

Conditions
ConditionsYield
With oxygen; tetraacetatodiruthenium chloride In toluene at 50℃; under 760.051 Torr; for 12h;A 4%
B 80%
With potassium carbonate; 1-(tert-butylperoxy)-1,2-benziodoxol-3(1H)-one In benzene for 3.5h; Ambient temperature;A 6%
B 76%
With sodium carbonate In ethyl acetate at 120℃; for 24h; Sealed tube; Green chemistry; Overall yield = 63 %;A 13%
B 50%
With [(η5-pentamethylcyclopentadienyl)IrCl(dipyrido[3,2-a:2',3'-c]phenazine)](CF3SO3) In aq. phosphate buffer at 37℃; for 48h; pH=7; Irradiation;
C13H13NO5

C13H13NO5

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

Conditions
ConditionsYield
In methanol at 50 - 55℃; for 3h; Bischler-Napieralski Reaction;80%
hexamethylenetetramine
100-97-0

hexamethylenetetramine

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

A

2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
16620-96-5

2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

B

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

Conditions
ConditionsYield
With formic acid for 1h; Pictet-Spengler reaction; Heating;A 78%
B 10%
(R)-(6-Bromo-benzo[1,3]dioxol-5-yl)-((S)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-yl)-methanol

(R)-(6-Bromo-benzo[1,3]dioxol-5-yl)-((S)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-yl)-methanol

A

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

B

3,4-dimethoxy-benzaldehyde
120-14-9

3,4-dimethoxy-benzaldehyde

C

(3,4-dimethoxyphenyl)methanol
93-03-8

(3,4-dimethoxyphenyl)methanol

(+/-)-trans-4H-1,2-dimethoxy-7-hydroxy-9,10-(methylenedioxy)5,6,6a,7-tetrahydrodibenzo[de,g]quinoline

(+/-)-trans-4H-1,2-dimethoxy-7-hydroxy-9,10-(methylenedioxy)5,6,6a,7-tetrahydrodibenzo[de,g]quinoline

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In toluene for 4h; Decomposition; radical cyclization; Heating;A 77%
B 10%
C 45%
D 14%
formaldehyd
50-00-0

formaldehyd

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

Conditions
ConditionsYield
for 0.5h; Reflux;70%
Pictet-Spengler reaction;
6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline monohydrochloride
2328-12-3

6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline monohydrochloride

A

6,7-dimethoxyisoquinoline
15248-39-2

6,7-dimethoxyisoquinoline

B

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

Conditions
ConditionsYield
With nickel(II) sulphate; sodium hydroxide; dipotassium peroxodisulfate In dichloromethane; water for 1h; Ambient temperature;A 6%
B 60%
(+/-)-1-(2-bromo-4,5-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
59444-59-6

(+/-)-1-(2-bromo-4,5-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

A

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

B

1,2-dimethoxy-4-methylbenzene
494-99-5

1,2-dimethoxy-4-methylbenzene

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In toluene for 4h; Decomposition; Heating;A 60%
B 60%
6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
1745-07-9

6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

A

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

B

4a-(6,7-Dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-5-ethyl-3,7,8,10-tetramethyl-5,10-dihydro-4aH-benzo[g]pteridine-2,4-dione

4a-(6,7-Dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-5-ethyl-3,7,8,10-tetramethyl-5,10-dihydro-4aH-benzo[g]pteridine-2,4-dione

Conditions
ConditionsYield
With air; FlEt+·ClO4- In acetonitrile at 37℃; for 552h; Title compound not separated from byproducts;A 200 % Spectr.
B 55%
nitromethane
75-52-5

nitromethane

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

Conditions
ConditionsYield
With polyphosphoric acid at 100℃; for 1.5h;50%
1,2,3,4-tetrahydro-6,7-dimethoxy-2-(3,4-dimethoxybenzyl)isoquinoline
91790-53-3

1,2,3,4-tetrahydro-6,7-dimethoxy-2-(3,4-dimethoxybenzyl)isoquinoline

A

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

B

3,4-dimethoxy-benzaldehyde
120-14-9

3,4-dimethoxy-benzaldehyde

C

Veratric acid
93-07-2

Veratric acid

Conditions
ConditionsYield
With sodium perchlorate In acetonitrile anode potential 0.95 - 1.1 V;A 16%
B 10%
C 8%
1,2,3,4-tetrahydro-6,7-dimethoxy-2-(3,4-dimethoxybenzyl)isoquinoline
91790-53-3

1,2,3,4-tetrahydro-6,7-dimethoxy-2-(3,4-dimethoxybenzyl)isoquinoline

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

Conditions
ConditionsYield
With manganese(IV) oxide; sulfuric acid
1-ethyl-9,10-dimethoxy-2-oxo-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline-3-carboxylic acid ethyl ester
100197-72-6

1-ethyl-9,10-dimethoxy-2-oxo-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline-3-carboxylic acid ethyl ester

A

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

B

1-ethyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-pyrido[2,1-a]isoquinolin-2-one
98146-15-7

1-ethyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-pyrido[2,1-a]isoquinolin-2-one

Conditions
ConditionsYield
With hydrogenchloride
1-isobutyl-9,10-dimethoxy-2-oxo-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline-3-carboxylic acid ethyl ester
114795-51-6

1-isobutyl-9,10-dimethoxy-2-oxo-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline-3-carboxylic acid ethyl ester

A

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

B

1-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-pyrido[2,1-a]isoquinolin-2-one
99672-64-7

1-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-pyrido[2,1-a]isoquinolin-2-one

Conditions
ConditionsYield
With hydrogenchloride
(+/-)-1-(2-bromo-4,5-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
59444-59-6

(+/-)-1-(2-bromo-4,5-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene for 18h; Heating;160 mg
formic acid
64-18-6

formic acid

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

Conditions
ConditionsYield
With trichlorophosphate at 190 - 200℃; for 2.5h; Yield given;
Stage #1: formic acid; 2-(3,4-dimethoxyphenyl)-ethylamine at 175℃; Inert atmosphere;
Stage #2: With trichlorophosphate In toluene at 95℃; Bischler-Napieralski Reaction; Inert atmosphere;
sulfuric acid
7664-93-9

sulfuric acid

Tetrahydropapaverine
13074-31-2

Tetrahydropapaverine

manganese dioxide

manganese dioxide

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

N-benzoyl-Py-tetrahydro-papaverine

N-benzoyl-Py-tetrahydro-papaverine

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

Conditions
ConditionsYield
With manganese(IV) oxide; sulfuric acid
sulfuric acid
7664-93-9

sulfuric acid

2-Benzoyl-1-<(3,4-dimethoxyphenyl)methyl>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
97157-25-0

2-Benzoyl-1-<(3,4-dimethoxyphenyl)methyl>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

manganese dioxide

manganese dioxide

A

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

B

3,4-dimethoxy-benzaldehyde
120-14-9

3,4-dimethoxy-benzaldehyde

C

benzoic acid
65-85-0

benzoic acid

N-[2-(3,4-dimethoxyphenyl)ethyl]formamide
14301-36-1

N-[2-(3,4-dimethoxyphenyl)ethyl]formamide

toluene
108-88-3

toluene

phosphorus pentoxide

phosphorus pentoxide

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

(+/-)-1-(2-bromo-4,5-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
59444-59-6

(+/-)-1-(2-bromo-4,5-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

A

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

B

6-deutero-3,4-dimethoxytoluene

6-deutero-3,4-dimethoxytoluene

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tributyltin deuteride In toluene for 4h; Decomposition; deuterium incorporation; Heating;
C20H23(2)HBrNO4

C20H23(2)HBrNO4

A

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

B

C9H11(2)HO2

C9H11(2)HO2

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In toluene for 4h; Decomposition; deuterium incorporation; Heating;
2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent / methanol / 12 h / Ambient temperature
2: 89 percent / POCl3 / toluene
View Scheme
Multi-step reaction with 2 steps
1: 80 percent / HCO2H
2: t-butyl hydroperoxide / RuCl2(PPh3)3
View Scheme
Multi-step reaction with 2 steps
1.1: toluene / 5 h / 25 - 45 °C
2.1: phosphoric acid / toluene / 5 h / 110 °C
2.2: pH ~ 8.3
View Scheme
6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

methyl iodide
74-88-4

methyl iodide

2-methyl-6,7-dimethoxy-3,4-dihydroisoquinolinium iodide
30045-07-9

2-methyl-6,7-dimethoxy-3,4-dihydroisoquinolinium iodide

Conditions
ConditionsYield
In diethyl ether at 20℃; Inert atmosphere;100%
In tetrahydrofuran
In acetonitrile at 80℃; for 2h;
6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

2-bromo-5-methoxybenzyl bromide
19614-12-1

2-bromo-5-methoxybenzyl bromide

2-(2-bromo-5-methoxybenzyl)-3,4-dihydro-6,7-dimethoxyisoquinolinium bromide

2-(2-bromo-5-methoxybenzyl)-3,4-dihydro-6,7-dimethoxyisoquinolinium bromide

Conditions
ConditionsYield
In diethyl ether Heating;100%
6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

A

(4R,11bS)-9,10-dimethoxy-4-propyl-3,4,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-2(11bH)-one
1421697-27-9

(4R,11bS)-9,10-dimethoxy-4-propyl-3,4,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-2(11bH)-one

B

(4S,11bS)-9,10-dimethoxy-4-propyl-3,4,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-2(11bH)-one
1421697-31-5

(4S,11bS)-9,10-dimethoxy-4-propyl-3,4,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-2(11bH)-one

Conditions
ConditionsYield
With (S)-2-(3-((1R,2R)-2-aminocyclohexyl)thioureido)-N-benzhydryl-N,3,3-trimethylbutanamide; acetic acid In toluene at 4℃; for 48h; Diels-Alder Cycloaddition; Inert atmosphere; enantioselective reaction;A 99%
B n/a
6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
1745-07-9

6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With butyl triphenylphosphonium tetraborate at 20℃; for 0.1h;98%
With 1-benzyl-1-azonia-4-azabicyclo[2.2.2]octane tetrahydroborate In tert-butyl alcohol at 20℃; for 0.2h; Reduction;95%
With benzyltriphenylphosphonium borohydride In methanol at 20℃; for 0.333333h;90%
2-bromo-2-(2-ethyl)dioxolane
18742-02-4

2-bromo-2-(2-ethyl)dioxolane

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

3,4-dihydro-6,7-dimethoxy-2-(3,3-ethylenedioxypropyl)isoquinolinium bromide
107020-15-5

3,4-dihydro-6,7-dimethoxy-2-(3,3-ethylenedioxypropyl)isoquinolinium bromide

Conditions
ConditionsYield
98%
In diethyl ether; ethanol for 20h; Heating;90%
3-cyano-4-methylpyridine
5444-01-9

3-cyano-4-methylpyridine

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

(+/-)-5,6,13,13a-tetrahydro-2,3-dimethoxy-8H-isoquino<2,1-b><2,7>naphthyridine-8-imine
109374-24-5

(+/-)-5,6,13,13a-tetrahydro-2,3-dimethoxy-8H-isoquino<2,1-b><2,7>naphthyridine-8-imine

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate; lithium hexamethyldisilazane In tetrahydrofuran -40 deg C, 4 h; room temp., 12 h;97.5%
Pyran-2-one-6-carbonyl chloride
75611-67-5

Pyran-2-one-6-carbonyl chloride

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

allyltributylstanane
24850-33-7

allyltributylstanane

(+/-)-1-allyl-6,7-dimethoxy-2-(2-oxo-2H-pyran-6-ylcarbonyl)-1,2,3,4-tetrahydroisoquinoline
122888-25-9

(+/-)-1-allyl-6,7-dimethoxy-2-(2-oxo-2H-pyran-6-ylcarbonyl)-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With 4 A molecular sieve In dichloromethane for 3.5h; Ambient temperature;97%
6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

2,3-dimethoxybenzyl chloride
3893-01-4

2,3-dimethoxybenzyl chloride

3,4-dihydro-6,7-dimethoxy-N-(2,3-dimethoxybenzyl)isoquinolinium chloride
75875-48-8

3,4-dihydro-6,7-dimethoxy-N-(2,3-dimethoxybenzyl)isoquinolinium chloride

Conditions
ConditionsYield
In benzene for 24h; Ambient temperature;97%
6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

dimedone
3471-13-4

dimedone

2-(6,7-Dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-yl)-3-hydroxy-5,5-dimethyl-cyclohex-2-enone
111599-09-8

2-(6,7-Dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-yl)-3-hydroxy-5,5-dimethyl-cyclohex-2-enone

Conditions
ConditionsYield
at 90℃; for 0.5h;96%
6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

methyl 2-(((tertbutoxycarbonyl)oxy)(4-chlorophenyl)methyl)acrylate
1132641-29-2

methyl 2-(((tertbutoxycarbonyl)oxy)(4-chlorophenyl)methyl)acrylate

C22H20ClNO4

C22H20ClNO4

Conditions
ConditionsYield
With iron(III) chloride In dimethyl sulfoxide at 130℃; for 4h; Morita-Baylis-Hillman Alkylation;96%
6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine
93102-05-7

N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine

2-benzyl-8,9-dimethoxy-1,2,3,5,6,10b-hexahydroimidazo[5,1-a]isoquinoline

2-benzyl-8,9-dimethoxy-1,2,3,5,6,10b-hexahydroimidazo[5,1-a]isoquinoline

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃; for 1h;96%
6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

bromoacetic acid methyl ester
96-32-2

bromoacetic acid methyl ester

6,7-Dimethoxy-(2-methoxycarbonylmethyl)-3,4-dihydroisoquinolin-2-ium bromide
84690-25-5

6,7-Dimethoxy-(2-methoxycarbonylmethyl)-3,4-dihydroisoquinolin-2-ium bromide

Conditions
ConditionsYield
In dichloromethane for 24h; Ambient temperature;95%
In diethyl ether at 20℃;
6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

2-nitrobenzyl chloride
612-23-7

2-nitrobenzyl chloride

3,4-dihydro-6,7-dimethoxy-2-[(2-nitrophenyl)methyl]isoquinolinium chloride

3,4-dihydro-6,7-dimethoxy-2-[(2-nitrophenyl)methyl]isoquinolinium chloride

Conditions
ConditionsYield
In diethyl ether at 20℃; for 72h;95%
potassium cyanide

potassium cyanide

6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile
1210-57-7

6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile

Conditions
ConditionsYield
With acetic acid In methanol at 0 - 20℃; for 1h; Inert atmosphere;95%
With hydrogenchloride In methanol; water at 0 - 20℃; for 17h;93%
With acetic acid In methanol at 0 - 20℃; for 1h;92%
With hydrogenchloride In methanol; water at 0 - 20℃; for 17h;88%
With hydrogenchloride at 20℃; Inert atmosphere;
6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

diisopropyl malonate
13195-64-7

diisopropyl malonate

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(R)-diisopropyl 2-(2-(tert-butoxycarbonyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)malonate
1091627-81-4

(R)-diisopropyl 2-(2-(tert-butoxycarbonyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)malonate

Conditions
ConditionsYield
Stage #1: 6,7-dimethoxy-3,4-dihydro-isoquinoline; di-tert-butyl dicarbonate In dichloromethane at 20℃; for 0.5h;
Stage #2: diisopropyl malonate In dichloromethane at 0 - 2.5℃; for 15h;
94%
Stage #1: 6,7-dimethoxy-3,4-dihydro-isoquinoline; di-tert-butyl dicarbonate In dichloromethane at 20℃; for 0.5h;
Stage #2: diisopropyl malonate In dichloromethane at 0 - 2.5℃; for 15h;
94%
Stage #1: 6,7-dimethoxy-3,4-dihydro-isoquinoline; di-tert-butyl dicarbonate In dichloromethane at 20℃; for 0.5h;
Stage #2: diisopropyl malonate; Pd-catalyst In dichloromethane at 0 - 2.5℃; for 15h;
94%
Stage #1: 6,7-dimethoxy-3,4-dihydro-isoquinoline; di-tert-butyl dicarbonate In dichloromethane at 20℃; for 0.5h;
Stage #2: diisopropyl malonate In dichloromethane at 0 - 2.5℃; for 15h;
94%
6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

malonic acid
141-82-2

malonic acid

2‐(6,7‐dimethoxy‐1,2,3,4‐tetrahydroisoquinolin‐1‐yl)acetic acid
68345-67-5

2‐(6,7‐dimethoxy‐1,2,3,4‐tetrahydroisoquinolin‐1‐yl)acetic acid

Conditions
ConditionsYield
for 1h; Heating;92%
at 120℃; for 1h;92%
6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

2-(tributylstannylmethyl)acrylonitrile

2-(tributylstannylmethyl)acrylonitrile

methyl chloroformate
79-22-1

methyl chloroformate

1-(2-Cyano-allyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid methyl ester

1-(2-Cyano-allyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid methyl ester

Conditions
ConditionsYield
In dichloromethane for 14h; Ambient temperature;91%
6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

2-(carbomethoxy)allyl tributyltin
132841-83-9

2-(carbomethoxy)allyl tributyltin

Allyl chloroformate
2937-50-0

Allyl chloroformate

6,7-Dimethoxy-1-(2-methoxycarbonyl-allyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid allyl ester

6,7-Dimethoxy-1-(2-methoxycarbonyl-allyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid allyl ester

Conditions
ConditionsYield
In dichloromethane for 4h; Ambient temperature;91%
6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

C13H12Cl2O

C13H12Cl2O

(Z)-2-(2-((1-(3,4-dichlorophenyl)-1-oxohept-2-en-3-yl)amino)ethyl)-4,5-dimethoxybenzaldehyde

(Z)-2-(2-((1-(3,4-dichlorophenyl)-1-oxohept-2-en-3-yl)amino)ethyl)-4,5-dimethoxybenzaldehyde

Conditions
ConditionsYield
With water; sodium chloride In toluene at 50℃; for 11h; stereoselective reaction;91%
6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

methyl 2-(((tert-butoxycarbonyl)oxy)(3,4-dichlorophenyl)methyl)acrylate
1132641-33-8

methyl 2-(((tert-butoxycarbonyl)oxy)(3,4-dichlorophenyl)methyl)acrylate

C22H19Cl2NO4

C22H19Cl2NO4

Conditions
ConditionsYield
With iron(III) chloride In dimethyl sulfoxide at 130℃; for 4h; Morita-Baylis-Hillman Alkylation;91%
6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

trans-chrotonyl chloride
625-35-4, 3488-22-0, 10487-71-5

trans-chrotonyl chloride

N-(2-formyl-4,5-dimethoxyphenetyl)crotonamide
94882-60-7

N-(2-formyl-4,5-dimethoxyphenetyl)crotonamide

Conditions
ConditionsYield
With sodium hydrogencarbonate In dichloromethane for 0.833333h;90%
With sodium hydrogencarbonate In dichloromethane; water Ambient temperature;75%
6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

2-(carbomethoxy)allyl tributyltin
132841-83-9

2-(carbomethoxy)allyl tributyltin

methyl chloroformate
79-22-1

methyl chloroformate

6,7-Dimethoxy-1-(2-methoxycarbonyl-allyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid methyl ester

6,7-Dimethoxy-1-(2-methoxycarbonyl-allyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid methyl ester

Conditions
ConditionsYield
In dichloromethane for 3.5h; Ambient temperature;90%
6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

acetyl chloride
75-36-5

acetyl chloride

N-[2-(2-formyl-4,5-dimethoxy-phenyl)-ethyl]-acetamide
203806-36-4

N-[2-(2-formyl-4,5-dimethoxy-phenyl)-ethyl]-acetamide

Conditions
ConditionsYield
With sodium hydrogencarbonate In dichloromethane for 1.5h; Ambient temperature;90%
6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

methyllithium
917-54-4

methyllithium

(6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline)
493-48-1, 5784-74-7, 38520-68-2, 54193-08-7

(6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline)

Conditions
ConditionsYield
With (-)-sparteine In tetrahydrofuran; diethyl ether at -20℃; for 2h;90%

3382-18-1Relevant articles and documents

-

Corrodi,Hillarp

, p. 2425 (1963)

-

Integrating Hydrogen Production with Aqueous Selective Semi-Dehydrogenation of Tetrahydroisoquinolines over a Ni2P Bifunctional Electrode

Huang, Chenqi,Huang, Yi,Liu, Cuibo,Yu, Yifu,Zhang, Bin

, p. 12014 - 12017 (2019)

Exploring an alternative anodic reaction to produce value-added chemicals with high selectivity, especially integrated with promoted hydrogen generation, is desirable. Herein, a selective semi-dehydrogenation of tetrahydroisoquinolines (THIQs) is demonstrated to replace the oxygen evolution reaction (OER) for boosting H2 evolution reaction (HER) in water over a Ni2P nanosheet electrode. The value-added semi-dehydrogenation products, dihydroisoquinolines (DHIQs), can be selectively obtained with high yields at the anode. The controllable semi-dehydrogenation is attributed to the in situ formed NiII/NiIII redox active species. Such a strategy can deliver a variety of DHIQs bearing electron-withdrawing/donating groups in good yields and excellent selectivities, and can be applied to gram-scale synthesis. A two-electrode Ni2P bifunctional electrolyzer can produce both H2 and DHIQs with robust stability and high Faradaic efficiencies at a much lower cell voltage than that of overall water splitting.

Integrating photocatalytic reduction of CO2 with selective oxidation of tetrahydroisoquinoline over InP–In2O3 Z-scheme p-n junction

Zhao, Bohang,Huang, Yi,Liu, Dali,Yu, Yifu,Zhang, Bin

, p. 28 - 34 (2020)

The development of a facile strategy to construct stable hierarchal porous heterogeneous photocatalysts remains a great challenge for efficient CO2 reduction. Additionally, hole-trapping sacrificial agents (e.g., triethanolamine, triethylamine, and methanol) are mostly necessary, which produce useless chemicals, and thus cause costs/environmental concerns. Therefore, utilizing oxidation ability of holes to develop an alternative photooxidation reaction to produce value-added chemicals, especially coupled with CO2 photoreduction, is highly desirable. Here, an in situ partial phosphating method of In2O3 is reported for synthesizing InP–In2O3 p-n junction. A highly selective photooxidation of tetrahydroisoquinoline (THIQ) into value-added dihydroisoquinoline (DHIQ) is to replace the hole driven oxidation of typical sacrificial agents. Meanwhile, the photoelectrons of InP–In2O3 p-n junction can induce the efficient photoreduction of CO2 to CO with high selectivity and stability. The evolution rates of DHIQ and CO are 2 and 3.8 times higher than those of the corresponding In2O3 n-type precursor, respectively. In situ irradiated X-ray photoelectron spectroscopy and electron spin resonance are utilized to confirm that the direct Z-scheme mechanism of InP–In2O3 p-n junction accelerate the efficient separation of photocarriers.

Gold(I)-Catalyzed Cyclization-3-Aza-Cope-Mannich Cascade and Its Application to the Synthesis of Cephalotaxine

Sakai, Takeo,Okumura, Chise,Futamura, Masatoshi,Noda, Naotaka,Nagae, Akari,Kitamoto, Chiharu,Kamiya, Madoka,Mori, Yuji

supporting information, p. 4391 - 4395 (2021/05/26)

The discovery of a new gold(I)-catalyzed cascade reaction involving cyclization onto a vinylammonium, 3-aza-Cope rearrangement, and Mannich cyclization is reported. A variety of fused nitrogen heterocycles were prepared from simple cyclic tertiary amines using 1-5 mol % of a AuCl(PPh3)/Ag[C5(CN)5] cocatalyst system. The developed reaction was used in a study aimed at synthesizing cephalotaxine. A five-step operation from norhydrastinine provided demethylcephalotaxinone in 39.1% overall yield, which was transformed to (-)-cephalotaxine in two steps.

Peganumine A alkaloid structure simplifier and application thereof

-

Paragraph 0037-0038; 0042-0044, (2021/06/26)

The invention discloses a Peganumine A alkaloid structure simplifier, a stereoisomer or a pharmaceutical salt thereof. The structure is shown in the following general formula: each substituent group is defined in the specification. The simplified structure of the Peganumine A alkaloid provided by the invention has a relatively obvious proliferation inhibition effect on liver cancer HepG2, lung cancer A549 and intestinal cancer HCT116, and the anti-tumor activity of part of compounds is higher than the anti-liver cancer HepG2 activity of Peganumine A reported in literatures.

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