(-)-(1R,4aS,8aS)-1β,2β,4aβ-trimethyl-1α-[(2',5'-dimethoxyphenyl)methyl]-5-exo-methylene-(3H)-1,4,4a,5,6,7,8,8a-octahydronaphthalene

Base Information

• Chemical Name: (-)-(1R,4aS,8aS)-1β,2β,4aβ-trimethyl-1α-[(2',5'-dimethoxyphenyl)methyl]-5-exo-methylene-(3H)-1,4,4a,5,6,7,8,8a-octahydronaphthalene
• CAS No.: 184485-50-5
• Molecular Formula: C₂₃H₃₄O₂
• Molecular Weight: 342.522
• Mol file: 184485-50-5.mol

Synonyms:(-)-(1R,4aS,8aS)-1β,2β,4aβ-trimethyl-1α-[(2',5'-dimethoxyphenyl)methyl]-5-exo-methylene-(3H)-1,4,4a,5,6,7,8,8a-octahydronaphthalene

Chemical Property of (-)-(1R,4aS,8aS)-1β,2β,4aβ-trimethyl-1α-[(2',5'-dimethoxyphenyl)methyl]-5-exo-methylene-(3H)-1,4,4a,5,6,7,8,8a-octahydronaphthalene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(1R,4aS,8aS)-1β,2β,4aβ-trimethyl-1α-[(2',5'-dimethoxyphenyl)methyl]-5-exo-methylene-(3H)-1,4,4a,5,6,7,8,8a-octahydronaphthalene

There total 11 articles about (-)-(1R,4aS,8aS)-1β,2β,4aβ-trimethyl-1α-[(2',5'-dimethoxyphenyl)methyl]-5-exo-methylene-(3H)-1,4,4a,5,6,7,8,8a-octahydronaphthalene 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: 97.0%

Methyltriphenylphosphonium bromide (1779-49-3) + (-)-(1R,4aS,8aS)-1β,2β,4aβ-trimethyl-1α-[(2',5'-dimethoyphenyl)methyl]-1,2,3,4,4a,5,6,7,8,8aα-decahydronaphthalen-5-one (184485-49-2) → (-)-(1R,4aS,8aS)-1β,2β,4aβ-trimethyl-1α-[(2',5'-dimethoxyphenyl)methyl]-5-exo-methylene-(3H)-1,4,4a,5,6,7,8,8a-octahydronaphthalene (184485-50-5)

Guidance literature:

With n-butyllithium; In 1,4-dioxane; hexane; 1.) room temperature, 1 h, 2.) reflux, 3 h;

DOI:10.1021/jo961048r

Reference yield: 90.0%

Methylenetriphenylphosphorane (19493-09-5) + (-)-(1R,4aS,8aS)-1β,2β,4aβ-trimethyl-1α-[(2',5'-dimethoyphenyl)methyl]-1,2,3,4,4a,5,6,7,8,8aα-decahydronaphthalen-5-one (184485-49-2) → (-)-(1R,4aS,8aS)-1β,2β,4aβ-trimethyl-1α-[(2',5'-dimethoxyphenyl)methyl]-5-exo-methylene-(3H)-1,4,4a,5,6,7,8,8a-octahydronaphthalene (184485-50-5)

Guidance literature:

In dimethyl sulfoxide; at 75 ℃; for 5h;

DOI:10.1021/jo962292l

Reference yield:

(4aS)-1,4aβ-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione-5-ethyeneacetal (26742-33-6) → (-)-(1R,4aS,8aS)-1β,2β,4aβ-trimethyl-1α-[(2',5'-dimethoxyphenyl)methyl]-5-exo-methylene-(3H)-1,4,4a,5,6,7,8,8a-octahydronaphthalene (184485-50-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / Li, liq. NH₃

2: 86 percent

3: PPTS / acetone

4: H₂, Et₃N / Pd/C

5: 85 percent

With ammonia; hydrogen; pyridinium p-toluenesulfonate; lithium; triethylamine; palladium on activated charcoal; In acetone;

DOI:10.1039/CC9960002717

upstream raw materials:

Methyltriphenylphosphonium bromide

(-)-(1R,4aS,8aS)-1β,2β,4aβ-trimethyl-1α-[(2',5'-dimethoyphenyl)methyl]-1,2,3,4,4a,5,6,7,8,8aα-decahydronaphthalen-5-one

Methylenetriphenylphosphorane

(4aS)-1,4aβ-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione-5-ethyeneacetal

Downstream raw materials:

avarol dimethyl ether

2-[[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-(methylene)decahydronaphthalen-1-yl]methyl]cyclohexa-2,5-diene-1,4-dione

avarone

avarol