(4aS)-5,5,8abeta-Trimethyldecalin-1-one

Base Information

• Chemical Name: (4aS)-5,5,8abeta-Trimethyldecalin-1-one
• CAS No.: 60134-39-6
• Molecular Formula: C₁₃H₂₂O
• Molecular Weight: 194.317
• DSSTox Substance ID: DTXSID801199313
• Nikkaji Number: J680.298B
• Mol file: 60134-39-6.mol

Synonyms:DTXSID801199313;(4aS)-5,5,8abeta-Trimethyldecalin-1-one;(4aS,8aS)-Octahydro-5,5,8a-trimethyl-1(2H)-naphthalenone;60134-39-6

Chemical Property of (4aS)-5,5,8abeta-Trimethyldecalin-1-one

Chemical Property:

• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 194.167065321
• Heavy Atom Count: 14
• Complexity: 254

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(CCCC2(C1CCCC2=O)C)C
• Isomeric SMILES: C[C@]12CCCC([C@@H]1CCCC2=O)(C)C

Technology Process of (4aS)-5,5,8abeta-Trimethyldecalin-1-one

There total 2 articles about (4aS)-5,5,8abeta-Trimethyldecalin-1-one 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:

manool (596-85-0) → (-)-(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalen-1(2H)-one (60134-39-6)

Guidance literature:

Multi-step reaction with 5 steps

1: (i) POCl₃, Py, (ii) O₃, EtOH, hexane, (iii) NaBH₄, EtOH

2: Py

3: POCl₃, Py

4: (i) H₂, Pd-C, MeOH, AcOEt, (ii) aq. KOH

5: aq. CrO₃, Py

With pyridine; chromium(VI) oxide; trichlorophosphate;

DOI:10.1002/hlca.19760590418

Reference yield:

(+)-confertifoline (1811-23-0) → (-)-(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalen-1(2H)-one (60134-39-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / LiAlH₄ / tetrahydrofuran / 2 h / Heating

2: 85 percent / mCPBA / CH₂Cl₂ / 1 h / 20 °C

3: 64 percent / LiAlH₄ / tetrahydrofuran / 4 h / Heating

4: 77 percent / NaIO₄ / tetrahydrofuran; H₂O / 0.25 h / 20 °C

5: 72 percent / Jones reagent / acetone / 10 °C

With sodium periodate; lithium aluminium tetrahydride; jones reagent; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; water; acetone;

DOI:10.1081/SCC-100104043

Reference yield: 71.0%

3-(phenylthio)-but-3-en-2-one (13522-48-0) + (-)-(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalen-1(2H)-one (60134-39-6) → 5,5,8aβ-trimethyl-2-(3-oxo-2-phenylthiobutyl)-4aα-perhydronaphthalen-1-one (91292-08-9)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; 1.) -78 deg C, 2 h, 2.) -78 deg C, 1 h; room temperature, 4 h;

upstream raw materials:

(+)-confertifoline

manool

Downstream raw materials:

5,5,8aβ-trimethyl-2-(3-oxo-2-phenylthiobutyl)-4aα-perhydronaphthalen-1-one

(2ζ,4aS,8aS)-2,5,5,8a-Tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1(2H)-one

methyl 4-[(1S,2S)-2-hydroxy-2,6,6-trimethylcyclohexyl]butanoate

2-[2-((1S,2S)-2-hydroxy-2,6,6-trimethylcyclohexyl)ethyl]butane-1,3-diol

Refernces