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473-03-0

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CAS No.: 473-03-0
Name: 1-(6-(2,2-dimethyl-6-methylenecyclohexyl)-4-methylhex-3-enyl)decahydro-2,5,5,8a-tetramethyl-2-naphthol
Article Data: 6
Molecular Structure:
Molecular Structure of 473-03-0 (1-(6-(2,2-dimethyl-6-methylenecyclohexyl)-4-methylhex-3-enyl)decahydro-2,5,5,8a-tetramethyl-2-naphthol)
Formula: C30H52 O
Molecular Weight: 428.742
Synonyms: 2-Naphthalenol,1-[6-(2,2-dimethyl-6-methylenecyclohexyl)-4-methyl-3-hexenyl]decahydro-2,5,5,8a-tetramethyl-,[1R-[1a[E(S*)],2b,4ab,8aa]]-; Ambra-13,18(28)-dien-8-ol (7CI); Ambra-13,18(28)-dien-8-ol, (E)-(8CI); (+)-Ambrein; Ambrein
Density: 0.94g/cm3
Boiling Point: 495.3°Cat760mmHg
Flash Point: 222°C
PSA: 20.23000
LogP: 8.86920
Related products
Synthetic route

(1R,2R,4aS,8aS,3'E,1"S)-(+)-1-[6'-(2",2"-dimethyl-6"-methylenecyclohexyl)-4'-methyl-3-hexenyl]-1,2,3,4,4a,5,6,7,8,8a-decahydro-2-tetrahydropyranyloxy-2,5,5,8a-tetramethylnaphthalene

A

473-03-0

(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

B

(1R,2R,4aS,8aS)-1-[(Z)-6-((S)-2,2-Dimethyl-6-methylene-cyclohexyl)-4-methyl-hex-3-enyl]-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-ol

Conditions
ConditionsYield
With bis(trimethylsilyl)sulphate In 1,2-dichloro-ethane for 0.0333333h; Ambient temperature;A 79%
B n/a
124462-97-1, 124579-43-7

<1R<2'RS,3'E(1'')R>,2R,4aS,8aS>-(+)-1-<2'-acetoxy-6'-(2'',2''-dimethyl-6''-methylenecyclohexyl)-4'-methyl-3'-hexenyl>-1,2,3,4,4a,5,6,7,8,8a-decahydro-2-(methoxymethyloxy)-2,5,5,8a-tetramethylnaphthalene

A

124462-99-3

(1R,2R,4aS,8aS)-1-[(E)-6-((S)-2,2-Dimethyl-6-methylene-cyclohexyl)-4-methyl-hex-2-enyl]-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-ol

B

473-03-0

(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions
ConditionsYield
With hydrogenchloride; lithium; acetic acid; tert-butyl alcohol 1. ethylamine, -78 deg C, 10 min 2. room temperature; Yield given. Multistep reaction. Yields of byproduct given;
13017-23-7

(4aR,6aS,10aS,10bR)-(-)-2,3,4a,5,6,6a,7,8,9,10,10a,10b-dodecahydro-4a,7,7,10a-tetramethyl-naphtho<2,1-b>pyran-3-ol

473-03-0

(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 90.1 percent / benzene / 15 h / 70 °C
2: 92.7 percent / TsOH / CH2Cl2 / 1 h / 0 °C
3: 96.2 percent / LiAlH4
4: 1.) LiCl, NaHCO3, 2,6-lutidine, 2.) MsCl / 1) DMF, 0 deg C, 50 min; 2) DMF, 0 deg C, 2.5 h
5: dimethylformamide / 12 h / Ambient temperature
6: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h
7: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C
8: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature
View Scheme
Multi-step reaction with 8 steps
1: 90.1 percent / benzene / 15 h / 70 °C
2: 92.7 percent / TsOH / CH2Cl2 / 1 h / 0 °C
3: 96.2 percent / LiAlH4
4: 1.) LiCl, NaHCO3, 2,6-lutidine, 2.) MsCl / 1) DMF, 0 deg C, 50 min; 2) DMF, 0 deg C, 2.5 h
5: dimethylformamide / 12 h / Ambient temperature
6: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h
7: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C
8: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature
View Scheme
166022-29-3

(S)-(+)-(2',2'-dimethyl-6'-methylene-1'-cyclohexyl)methanol

473-03-0

(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: pyridine / 1 h / 0 °C
2: NaBr / dimethylformamide / 5 h / 90 °C
3: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h
4: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C
5: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature
View Scheme
Multi-step reaction with 4 steps
1: 80 percent / CCl4, trioctylphosphine / 75 °C
2: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h
3: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C
4: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature
View Scheme
166022-22-6

(1S)-(+)-2,2-dimethyl-6-methylene-1-cyclohexanecarboxylic acid

473-03-0

(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 99.4 percent
2: 90.6 percent / LiAlH4
3: pyridine / 1 h / 0 °C
4: NaBr / dimethylformamide / 5 h / 90 °C
5: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h
6: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C
7: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature
View Scheme
Multi-step reaction with 6 steps
1: 99.4 percent
2: 90.6 percent / LiAlH4
3: 80 percent / CCl4, trioctylphosphine / 75 °C
4: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h
5: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C
6: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature
View Scheme
166239-08-3

methyl (1S)-(+)-2,2-dimethyl-6-methylene-1-cyclohexanecarboxylate

473-03-0

(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 90.6 percent / LiAlH4
2: pyridine / 1 h / 0 °C
3: NaBr / dimethylformamide / 5 h / 90 °C
4: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h
5: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C
6: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature
View Scheme
Multi-step reaction with 5 steps
1: 90.6 percent / LiAlH4
2: 80 percent / CCl4, trioctylphosphine / 75 °C
3: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h
4: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C
5: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature
View Scheme
188539-96-0

Methanesulfonic acid (1S,2R,4aS,8aS)-2,5,5,8a-tetramethyl-2-(tetrahydro-pyran-2-yloxy)-decahydro-naphthalen-1-ylmethyl ester

473-03-0

(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 1.) NaOMe, 2.) 18-crown-6 / 1) MeOH, 30 deg C, 30 min; 2) MeOH, HMPA, 68 deg C, 12 h
2: 92.1 percent / KOH / ethanol / 1.5 h / 55 °C
3: 71.1 percent / DIBAL / toluene / 1 h / -65 °C
4: 90.1 percent / benzene / 15 h / 70 °C
5: 92.7 percent / TsOH / CH2Cl2 / 1 h / 0 °C
6: 96.2 percent / LiAlH4
7: 1.) LiCl, NaHCO3, 2,6-lutidine, 2.) MsCl / 1) DMF, 0 deg C, 50 min; 2) DMF, 0 deg C, 2.5 h
8: dimethylformamide / 12 h / Ambient temperature
9: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h
10: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C
11: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature
View Scheme
Multi-step reaction with 11 steps
1: 1.) NaOMe, 2.) 18-crown-6 / 1) MeOH, 30 deg C, 30 min; 2) MeOH, HMPA, 68 deg C, 12 h
2: 92.1 percent / KOH / ethanol / 1.5 h / 55 °C
3: 71.1 percent / DIBAL / toluene / 1 h / -65 °C
4: 90.1 percent / benzene / 15 h / 70 °C
5: 92.7 percent / TsOH / CH2Cl2 / 1 h / 0 °C
6: 96.2 percent / LiAlH4
7: 1.) LiCl, NaHCO3, 2,6-lutidine, 2.) MsCl / 1) DMF, 0 deg C, 50 min; 2) DMF, 0 deg C, 2.5 h
8: dimethylformamide / 12 h / Ambient temperature
9: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h
10: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C
11: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature
View Scheme
188559-02-6

(S)-2-Chloromethyl-1,1-dimethyl-3-methylene-cyclohexane

473-03-0

(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h
2: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C
3: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature
View Scheme
188559-03-7

(S)-2-Bromomethyl-1,1-dimethyl-3-methylene-cyclohexane

473-03-0

(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h
2: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C
3: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature
View Scheme
188540-03-6

Methanesulfonic acid (S)-2,2-dimethyl-6-methylene-cyclohexylmethyl ester

473-03-0

(1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: NaBr / dimethylformamide / 5 h / 90 °C
2: 1.) BuLi / 1) hexane, THF, HMPA, -30 deg C, 15 min; 2) THF, hexane, HMPA, -30 --> 10 deg C, 3 h
3: PdCl2(dppp), LiHBEt3 / tetrahydrofuran / 8 h / 0 °C
4: 79 percent / bis(trimethylsilyl) sulfate / 1,2-dichloro-ethane / 0.03 h / Ambient temperature
View Scheme
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