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CAS No.: | 485-71-2 |
---|---|
Name: | Cinchonidine |
Article Data: | 21 |
Molecular Structure: | |
Formula: | C19H22N2O |
Molecular Weight: | 294.396 |
Synonyms: | Cinchonan-9-ol, (8alpha,9R)-;(R)-[(4R,5S,7R)-5-ethenyl-1-azoniabicyclo[2.2.2]oct-7-yl]-quinolin-4-yl-methanol;(R)-[(5S,7S)-5-ethenyl-1-azabicyclo[2.2.2]oct-7-yl]-quinolin-4-yl-methanol;(R)-[(4S,5S,7R)-5-ethenyl-1-azoniabicyclo[2.2.2]oct-7-yl]-quinolin-4-yl-methanol;Cinchonan-9-ol, (8R,9R)-;Cinchonan-9-ol, (8-alpha,9R)- (9CI);2-Quinuclidinemethanol, alpha-4-quinolyl-5-vinyl-;(R)-[(4S,5S,7S)-5-ethenyl-1-azabicyclo[2.2.2]oct-7-yl]-quinolin-4-yl-methanol;(8S,9R)-Cinchonidine;alpha-Quinidine;(8-alpha,9R)-Cinchonan-9-ol; |
EINECS: | 207-622-3 |
Density: | 1.204 g/cm3 |
Melting Point: | 204-206 °C(lit.) |
Boiling Point: | 464.502 °C at 760 mmHg |
Flash Point: | 234.723 °C |
Solubility: | insoluble in water |
Appearance: | white to light yellow crystal powder |
Hazard Symbols: | Xn,Xi |
Risk Codes: | 20/21/22-42/43-36/37/38 |
Safety: | 22-24/25-36/37-26 |
Transport Information: | UN 1544 |
PSA: | 36.36000 |
LogP: | 3.10250 |
Cinchonidin
Conditions | Yield |
---|---|
With potassium 4-(methoxy)phenyltrifluoroborate In dimethyl sulfoxide at 37℃; for 10h; Inert atmosphere; | 64% |
O-tosylcinchonidine
A
(Z)-1-(quinolin-4-yl)-3-((3R,4R)-3-vinylpiperidin-4-yl)prop-1-enyl 4-methylbenzene sulfonate
B
(1S,3R,4S,8S,9S)-9-hydroxy-cinchonane
C
Cinchonidin
Conditions | Yield |
---|---|
With salicylic acid In ethylene glycol at 95℃; for 0.25h; Microwave irradiation; | A 40% B 20% C 10% |
Cinchonidin
Conditions | Yield |
---|---|
ueber mehrere Stufen; |
pentan-1-ol
Cinchonin
A
(1S,3R,4S,8S,9S)-9-hydroxy-cinchonane
B
Cinchonidin
Conditions | Yield |
---|---|
Product distribution; |
Conditions | Yield |
---|---|
With potassium hydroxide; pentan-1-ol |
Conditions | Yield |
---|---|
In tetrahydrofuran at -10 - 20℃; for 5h; Inert atmosphere; | 100% |
In tetrahydrofuran at -10 - 50℃; for 6h; Inert atmosphere; Schlenk technique; | 100% |
In tetrahydrofuran at -78.16℃; for 12h; Inert atmosphere; | 14% |
In tetrahydrofuran at -78.16℃; for 12h; Inert atmosphere; | 14% |
benzyl chloride
Cinchonidin
(8S,9R)-(-)-N-benzylcinchonidinium chloride
Conditions | Yield |
---|---|
In toluene for 2h; Reflux; | 100% |
With sodium iodide In tetrahydrofuran at 20℃; Reflux; |
3,5-bistrifluoromethylphenylisothiocyanate
Cinchonidin
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 12h; Inert atmosphere; | 99% |
2-{3-[(1R)-3-(3,4-dimethoxyphenyl)-1-hydroxypropyl]phenoxy}acetic acid
Cinchonidin
Conditions | Yield |
---|---|
In ethyl acetate at 50℃; for 1h; | 99% |
The Cinchonidine, with the CAS registry number 485-71-2, is also known as (8S,9R)-Cinchonidine. It belongs to the product categories of Cyclic compounds; Alkaloids; Chiral; Biochemistry; Optical Resolution; Quinoline Alkaloids; Quinoline carboxylic Acids, etc.; Quinolines; Synthetic Organic Chemistry; Aromatics; Chiral Reagents; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals. Its EINECS number is 207-622-3. This chemical's molecular formula is C19H22N2O and molecular weight is 294.39. What's more, its systematic name is (8α,9R)-Cinchonan-9-ol. Its classification codes are: (1)Drug / Therapeutic Agent; (2)Natural Product. This chemical is an alkaloid found in Cinchona officinalis. It is used in asymmetric synthesis in organic chemistry. It is a stereoisomer and pseudo-enantiomer of cinchonine. This chemcial should be sealed and stored in a ventilated and dry place. Moreover, it should be protected from oxides.
Physical properties of Cinchonidine are: (1)ACD/LogP: 2.788; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.29; (4)ACD/LogD (pH 7.4): 0.90; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 10.06; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 36.36 Å2; (13)Index of Refraction: 1.652; (14)Molar Refractivity: 89.424 cm3; (15)Molar Volume: 244.537 cm3; (16)Polarizability: 35.45×10-24cm3; (17)Surface Tension: 56.4 dyne/cm; (18)Density: 1.204 g/cm3; (19)Flash Point: 234.723 °C; (20)Enthalpy of Vaporization: 76.485 kJ/mol; (21)Boiling Point: 464.502 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.
Uses of Cinchonidine: it can be used to produce N-(p-bromobenzyl)-cinchonidinium bromide at the ambient temperature. It will need solvent CH2Cl2 with the reaction time of 17 hours. The yield is about 65%.
When you are using this chemical, please be cautious about it as the following:
This chemcial is harmful by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin. This substance may cause sensitisation by inhalation and skin contact. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. You should not breathe dust. When using it, you need wear suitable protective clothing and gloves and you must avoid contact with skin and eyes.
You can still convert the following datas into molecular structure:
(1)SMILES: n2c1c(cccc1)c(cc2)[C@@H](O)[C@H]3N4CC[C@@H](C3)[C@@H](/C=C)C4
(2)Std. InChI: InChI=1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13-,14-,18-,19+/m0/s1
(3)Std. InChIKey: KMPWYEUPVWOPIM-KODHJQJWSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
quail | LD50 | oral | > 316mg/kg (316mg/kg) | Ecotoxicology and Environmental Safety. Vol. 6, Pg. 149, 1982. | |
rat | LD50 | intraperitoneal | 206mg/kg (206mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) | Acta Pharmacologica et Toxicologica. Vol. 4, Pg. 265, 1948. |