Methyl (alphaS,2R,4aS)-1,2,3,4,4a,7-hexahydro-alpha,4a,8-trimethyl-7-oxo-2-naphthaleneacetate

Base Information

• Chemical Name: Methyl (alphaS,2R,4aS)-1,2,3,4,4a,7-hexahydro-alpha,4a,8-trimethyl-7-oxo-2-naphthaleneacetate
• CAS No.: 18172-86-6
• Molecular Formula: C₁₆H₂₂O₃
• Molecular Weight: 262.349
• DSSTox Substance ID: DTXSID301127696
• Mol file: 18172-86-6.mol

Synonyms:DTXSID301127696;18172-86-6;Methyl (alphaS,2R,4aS)-1,2,3,4,4a,7-hexahydro-alpha,4a,8-trimethyl-7-oxo-2-naphthaleneacetate

Chemical Property of Methyl (alphaS,2R,4aS)-1,2,3,4,4a,7-hexahydro-alpha,4a,8-trimethyl-7-oxo-2-naphthaleneacetate

Chemical Property:

• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 262.15689456
• Heavy Atom Count: 19
• Complexity: 472

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2CC(CCC2(C=CC1=O)C)C(C)C(=O)OC
• Isomeric SMILES: CC1=C2C[C@@H](CC[C@]2(C=CC1=O)C)[C@H](C)C(=O)OC

Technology Process of Methyl (alphaS,2R,4aS)-1,2,3,4,4a,7-hexahydro-alpha,4a,8-trimethyl-7-oxo-2-naphthaleneacetate

There total 1 articles about Methyl (alphaS,2R,4aS)-1,2,3,4,4a,7-hexahydro-alpha,4a,8-trimethyl-7-oxo-2-naphthaleneacetate 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: 68.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + sodium thiophenolate (930-69-8) + santonin (481-06-1) → methyl (11S)-3-oxo-7αH-eudesma-1,4-dien-12-oate (18172-86-6) + methyl (11S)-1β-phenylthio-3-oxoeudesm-4-en-13-oate (135441-95-1)

Guidance literature:

sodium thiophenolate; santonin; In ethanol; for 20h; Heating;

diazomethane; In diethyl ether; at 0 ℃; for 1h;

DOI:10.1021/jo034129d

Reference yield:

methyl (11S)-3-oxo-7αH-eudesma-1,4-dien-12-oate (18172-86-6) → eudesma-4,11-dien-3-one (473-08-5)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / Rh catalyst / benzene

2: (i) LiAlH₄, Et₂O, (ii) DDQ, dioxane

3: Py

4: 400 °C

With pyridine; hydrogen; Rh catalyst; In benzene;

DOI:10.1139/v68-060

Reference yield:

methyl (11S)-3-oxo-7αH-eudesma-1,4-dien-12-oate (18172-86-6) → (2R,5R,10R,11S)-12-(o-nitrophenylselenenyl)-6-spirovetivene

Guidance literature:

Multi-step reaction with 8 steps

1.1: MeLi; CuCN / tetrahydrofuran; hexamethylphosphoric acid triamide; diethyl ether / 0.5 h / 0 °C

1.2: 85 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; diethyl ether / 0.33 h / -23 °C

2.1: 98 percent / BF₃*Et₂O / acetic acid / 7 h / 20 °C

3.1: 59 percent / Ca; liquid NH₃ / diethyl ether / 5 h / Heating

4.1: 91 percent / NaHCO₃; 18-crown-6; oxone / H₂O; acetone; CH₂Cl₂ / 1.5 h / 0 °C

5.1: 64 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h / -40 °C

6.1: 43 percent / H₂ / Pd/C / ethanol / 2 h

7.1: 86 percent / pyridine; n-Bu₃P / tetrahydrofuran / 18 h

8.1: TsOH / benzene / 0.75 h / Heating

With pyridine; Oxone; 18-crown-6 ether; tributylphosphine; boron trifluoride diethyl etherate; ammonia; methyllithium; hydrogen; sodium hydrogencarbonate; calcium; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; water; acetic acid; acetone; benzene;

DOI:10.1021/jo040189n

upstream raw materials:

diazomethane

sodium thiophenolate

santonin

Downstream raw materials:

(2R,5R,10S)-6,11-spirovetivadien-10-ol

(2R,5R,10S,11S)-12-(o-nitrophenylselenenyl)-6-spirovetivene

(2R,5R,6S)-6,10-Dimethyl-2-[(S)-1-methyl-2-(2-nitro-phenylselanyl)-ethyl]-spiro[4.5]dec-9-en-6-ol

(2R,5R,6S,10R,11S)-12-(o-nitrophenylselenenyl)-6-spirovetivanol

Refernces