Ambrein

Base Information

• Chemical Name: Ambrein
• CAS No.: 473-03-0
• Molecular Formula: C30H52 O
• Molecular Weight: 428.742
• European Community (EC) Number: 207-460-3
• UNII: 1N9JB373FJ
• ChEMBL ID: CHEMBL376021
• DSSTox Substance ID: DTXSID00883390
• Metabolomics Workbench ID: 176190
• Nikkaji Number: J11.891E
• Wikidata: Q104936334
• Wikipedia: Ambrein
• Mol file: 473-03-0.mol

Synonyms:1-(6-(2,2-dimethyl-6-methylenecyclohexyl)-4-methyl-3-hexenyl)decahydro-2,5,5,8a-tetramethyl-2-naphthalenol;ambrein

Chemical Property of Ambrein

Chemical Property:

• Vapor Pressure: 6.9E-12mmHg at 25°C
• Boiling Point: 495.3°Cat760mmHg
• Flash Point: 222°C
• PSA: 20.23000
• Density: 0.94g/cm³
• LogP: 8.86920
• XLogP3: 9.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 6
• Exact Mass: 428.401816278
• Heavy Atom Count: 31
• Complexity: 683

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC1C2(CCCC(C2CCC1(C)O)(C)C)C)CCC3C(=C)CCCC3(C)C
• Isomeric SMILES: C/C(=C\CC[C@@H]1[C@]2(CCCC([C@@H]2CC[C@@]1(C)O)(C)C)C)/CC[C@@H]3C(=C)CCCC3(C)C

Technology Process of Ambrein

There total 55 articles about Ambrein which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

(1R,2R,4aS,8aS,3'E,1S)-(+)-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 → (1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol (473-03-0) + (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

Guidance literature:

With bis(trimethylsilyl)sulphate; In 1,2-dichloro-ethane; for 0.0333333h; Ambient temperature;

DOI:10.1016/S0040-4020(97)00103-8

Reference yield:

(S)-1,1-dimethyl-3-methylene-2-((3E,7E,11E)-3,8,12,16-tetramethyl heptadeca-3,7,11,15-tetraen-1-yl)cyclohexane (140844-96-8) → (1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol (473-03-0)

Guidance literature:

With Triton X-100; cell-free extract B of tetraprenyl-β-curcumene cyclase; In aq. buffer; at 30 ℃; for 16h;

Reference yield:

(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 (13017-23-7) → (1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol (473-03-0)

Guidance literature:

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

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; n-butyllithium; bis(diphenylphosphino)propanepalladium(II) dichloride; bis(trimethylsilyl)sulphate; lithium triethylborohydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; methanesulfonyl chloride; lithium chloride; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4020(97)00103-8

upstream raw materials:

2-{(1S,2R,4aR,8aS)-1-[(E)-6-(2,2-Dimethyl-6-methylene-cyclohexyl)-4-methyl-hex-3-enyl]-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-yloxy}-tetrahydro-pyran

2,2-dimethyl-6-methylenecyclohexane-1-carbaldehyde

1-bromomethyl-3,3-dimethyl-1-cyclohexene

(2,2-dimethyl-6-methylenecyclohexyl)methanol

Downstream raw materials:

ambreinolide

(3aR)-(+)-sclareolide

formic acid

(S)-1.1-dimethyl-2-(3-oxo-butyl)-cyclohexanone-⁽³⁾

Refernces

• 1、 Tenkovskaia, Liudmila,Murakami, Mizuki,Okuno, Kotone,Ueda, Daijiro,Sato, Tsutomu. "Analysis of the Catalytic Mechanism of Bifunctional Triterpene/Sesquarterpene Cyclase: Tyr167 Functions To Terminate Cyclization of Squalene at the Bicyclic Step". . p. 1910 - 1913. Retrieved 2017/09/28.
• 2、 Tanimoto, Hisahide,Oritani, Takayuki. "Synthesis of (+)-Ambrein". . p. 3527 - 3536. Retrieved 2007/10/03.