(4aS,6aS,8R,11aS,11bS)-4,4,9,11b-Tetramethyl-1,2,3,4,4a,5,6,6a,7,8,11,11b-dodecahydro-8,11a-methanocyclohepta[a]naphthalene

Base Information

• Chemical Name: (4aS,6aS,8R,11aS,11bS)-4,4,9,11b-Tetramethyl-1,2,3,4,4a,5,6,6a,7,8,11,11b-dodecahydro-8,11a-methanocyclohepta[a]naphthalene
• CAS No.: 52645-90-6
• Molecular Formula: C20H32
• Molecular Weight: 272.4681
• DSSTox Substance ID: DTXSID70579298
• Metabolomics Workbench ID: 70973
• Nikkaji Number: J1.496.973J
• Wikidata: Q105196963
• Mol file: 52645-90-6.mol

Synonyms:Aphidicol-15-ene;52645-90-6;C11892;DTXSID70579298;(4aS,6aS,8R,11aS,11bS)-4,4,9,11b-Tetramethyl-1,2,3,4,4a,5,6,6a,7,8,11,11b-dodecahydro-8,11a-methanocyclohepta[a]naphthalene

Chemical Property of (4aS,6aS,8R,11aS,11bS)-4,4,9,11b-Tetramethyl-1,2,3,4,4a,5,6,6a,7,8,11,11b-dodecahydro-8,11a-methanocyclohepta[a]naphthalene

Chemical Property:

• Vapor Pressure: 0.000115mmHg at 25°C
• Boiling Point: 346.4°Cat760mmHg
• Flash Point: 170.2°C
• PSA: 0.00000
• Density: 0.97g/cm³
• LogP: 5.97540
• XLogP3: 6.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 272.250401021
• Heavy Atom Count: 20
• Complexity: 457

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCC23CC1CC2CCC4C3(CCCC4(C)C)C
• Isomeric SMILES: CC1=CC[C@]23C[C@H]1C[C@@H]2CC[C@@H]4[C@@]3(CCCC4(C)C)C

Technology Process of (4aS,6aS,8R,11aS,11bS)-4,4,9,11b-Tetramethyl-1,2,3,4,4a,5,6,6a,7,8,11,11b-dodecahydro-8,11a-methanocyclohepta[a]naphthalene

There total 21 articles about (4aS,6aS,8R,11aS,11bS)-4,4,9,11b-Tetramethyl-1,2,3,4,4a,5,6,6a,7,8,11,11b-dodecahydro-8,11a-methanocyclohepta[a]naphthalene 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: 60.0%

C27H40O3S (85706-63-4,93602-51-8) → (+)-aphidicolin-15-ene (41703-78-0,52645-90-6,96193-15-6)

Guidance literature:

With methyl sulfinyl carbanion; In dimethyl sulfoxide; at 60 ℃; for 2h;

DOI:10.1139/v84-331

Reference yield:

aphidicolan-16β-ol (101143-85-5) → aphidicol-16-en (52592-29-7) + aphidicol-15-ene (52645-90-6)

Guidance literature:

With methanesulfonyl chloride; triethylamine; In tetrahydrofuran; at -25 ℃; for 1h; Title compound not separated from byproducts;

DOI:10.1016/S0040-4020(99)00392-0

Reference yield:

Aphidicolin (38966-21-1,52645-92-8,52645-96-2,69926-98-3,79254-70-9) → aphidicol-15-ene (52645-90-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 77 percent / pyridine / 0.75 h / 20 °C

2: 12.6 mg / LiBH(Et)3 / tetrahydrofuran / 0.25 h / 20 °C

3: 73 percent / NaH / dimethylformamide / 13 h / 90 °C

4: 2.6 mg / hydrogen / Raney Ni / ethanol / 2 h / Heating

5: triethylamine; MsCl / tetrahydrofuran / 1 h / -25 °C

With pyridine; hydrogen; sodium hydride; lithium triethylborohydride; methanesulfonyl chloride; triethylamine; nickel; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; 1: Esterification / 2: Reduction / 3: Elimination / 4: Hydrogenation / 5: Elimination;

DOI:10.1016/S0040-4020(99)00392-0

upstream raw materials:

17-noraphidicolan-16-one

methyl-triphenylphosphonium iodide

aphidicolan-16β-ol

17,18-diacetoxyaphidicol-3α,16β-diol