trans-octahydro-1α-<(2,5-dimethoxyphenyl)methyl>-1β,4aβ-dimethyl-5β-hydroxy-2(1H)-naphthalenone

Base Information

• Chemical Name: trans-octahydro-1α-<(2,5-dimethoxyphenyl)methyl>-1β,4aβ-dimethyl-5β-hydroxy-2(1H)-naphthalenone
• CAS No.: 80765-03-3
• Molecular Formula: C₂₁H₃₀O₄
• Molecular Weight: 346.467
• Mol file: 80765-03-3.mol

Synonyms:trans-octahydro-1α-<(2,5-dimethoxyphenyl)methyl>-1β,4aβ-dimethyl-5β-hydroxy-2(1H)-naphthalenone

Chemical Property of trans-octahydro-1α-<(2,5-dimethoxyphenyl)methyl>-1β,4aβ-dimethyl-5β-hydroxy-2(1H)-naphthalenone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans-octahydro-1α-<(2,5-dimethoxyphenyl)methyl>-1β,4aβ-dimethyl-5β-hydroxy-2(1H)-naphthalenone

There total 1 articles about trans-octahydro-1α-<(2,5-dimethoxyphenyl)methyl>-1β,4aβ-dimethyl-5β-hydroxy-2(1H)-naphthalenone 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:

2,5-dimethoxybenzyl bromide (60732-17-4) + (+/-)-(4aβ,5β)-4,4a,5,6,7,8-hexahydro-5-hydroxy-1,4a-dimethylnaphthalen-2(3H)-one (24138-10-1,26742-30-3,38405-15-1,52842-07-6,102058-65-1) → trans-octahydro-1α-<(2,5-dimethoxyphenyl)methyl>-1β,4aβ-dimethyl-5β-hydroxy-2(1H)-naphthalenone (80765-03-3)

Guidance literature:

With lithium; Yield given. Multistep reaction; 1.) NH₃ (liquid), THF, 0.5 h, 2.) 15 min;

DOI:10.1021/jo00348a025

Reference yield: 85.0%

trans-octahydro-1α-<(2,5-dimethoxyphenyl)methyl>-1β,4aβ-dimethyl-5β-hydroxy-2(1H)-naphthalenone (80765-03-3) + Methylenetriphenylphosphorane (19493-09-5) → trans-decahydro-5α-<(2,5-dimethoxyphenyl)methyl>-5β,8aβ-dimethyl-6-methylene-1-naphthalenol (80765-04-4)

Guidance literature:

In dimethyl sulfoxide; at 75 - 80 ℃; for 40h;

DOI:10.1021/jo00348a025

Reference yield:

trans-octahydro-1α-<(2,5-dimethoxyphenyl)methyl>-1β,4aβ-dimethyl-5β-hydroxy-2(1H)-naphthalenone (80765-03-3) → trans-octahydro-5α-<(2,5-dimethoxyphenyl)methyl>-5β,6β,8aβ-trimethyl-1(2H)-naphthalenone (80765-07-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / dimethylsulfoxide / 40 h / 75 - 80 °C

2: 80 percent / H₂, methanol / 10percent Pd/C / triethylamine / 6 h / 30 °C / 760 Torr

3: 90 percent / pyridinium chlorochromate / CH₂Cl₂ / 2 h / 30 °C

With methanol; hydrogen; pyridinium chlorochromate; palladium on activated charcoal; In dichloromethane; dimethyl sulfoxide; triethylamine;

DOI:10.1021/jo00348a025

upstream raw materials:

2,5-dimethoxybenzyl bromide

(+/-)-(4aβ,5β)-4,4a,5,6,7,8-hexahydro-5-hydroxy-1,4a-dimethylnaphthalen-2(3H)-one

Downstream raw materials:

trans-decahydro-5α-<(2,5-dimethoxyphenyl)methyl>-5β,8aβ-dimethyl-6-methylene-1-naphthalenol

(+/-)-avarol dimethyl ether

trans-octahydro-5α-<(2,5-dimethoxyphenyl)methyl>-5β,6β,8aβ-trimethyl-1(2H)-naphthalenone

(+/-)-avarol