(1S,4aS)-(+)-trans-1α-[(2,5-dimethoxyphenyl)methyl]-1β,4aβ-dimethyl-5-(2-methyl-1,3-dioxolan-2-yl)-2-methyleneoctahydro-5(6H)-naphthalenone

Base Information

• Chemical Name: (1S,4aS)-(+)-trans-1α-[(2,5-dimethoxyphenyl)methyl]-1β,4aβ-dimethyl-5-(2-methyl-1,3-dioxolan-2-yl)-2-methyleneoctahydro-5(6H)-naphthalenone
• CAS No.: 184485-47-0
• Molecular Formula: C₂₄H₃₄O₄
• Molecular Weight: 386.532
• Mol file: 184485-47-0.mol

Synonyms:(1S,4aS)-(+)-trans-1α-[(2,5-dimethoxyphenyl)methyl]-1β,4aβ-dimethyl-5-(2-methyl-1,3-dioxolan-2-yl)-2-methyleneoctahydro-5(6H)-naphthalenone

Chemical Property of (1S,4aS)-(+)-trans-1α-[(2,5-dimethoxyphenyl)methyl]-1β,4aβ-dimethyl-5-(2-methyl-1,3-dioxolan-2-yl)-2-methyleneoctahydro-5(6H)-naphthalenone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4aS)-(+)-trans-1α-[(2,5-dimethoxyphenyl)methyl]-1β,4aβ-dimethyl-5-(2-methyl-1,3-dioxolan-2-yl)-2-methyleneoctahydro-5(6H)-naphthalenone

There total 7 articles about (1S,4aS)-(+)-trans-1α-[(2,5-dimethoxyphenyl)methyl]-1β,4aβ-dimethyl-5-(2-methyl-1,3-dioxolan-2-yl)-2-methyleneoctahydro-5(6H)-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: 86.0%

Methylenetriphenylphosphorane (19493-09-5) + (1S,4aS)-(+)-trans-1α-[(2,5-dimethoxyphenyl)methyl]-1β,4aβ-dimethyl-5-(2-methyl-1,3-dioxolan-2-yl)-hexahydro-2,5(3H,6H)-naphthalenedione (184485-46-9) → (1S,4aS)-(+)-trans-1α-[(2,5-dimethoxyphenyl)methyl]-1β,4aβ-dimethyl-5-(2-methyl-1,3-dioxolan-2-yl)-2-methyleneoctahydro-5(6H)-naphthalenone (184485-47-0)

Guidance literature:

DOI:10.1039/CC9960002717

Reference yield: 70.0%

Methyltriphenylphosphonium bromide (1779-49-3) + (1S,4aS)-(+)-trans-1α-[(2,5-dimethoxyphenyl)methyl]-1β,4aβ-dimethyl-5-(2-methyl-1,3-dioxolan-2-yl)-hexahydro-2,5(3H,6H)-naphthalenedione (184485-46-9) → (1S,4aS)-(+)-trans-1α-[(2,5-dimethoxyphenyl)methyl]-1β,4aβ-dimethyl-5-(2-methyl-1,3-dioxolan-2-yl)-2-methyleneoctahydro-5(6H)-naphthalenone (184485-47-0)

Guidance literature:

With n-butyllithium; In 1,4-dioxane; hexane; 1.) room temperature, 60 min, 2.) reflux, 24 h;

DOI:10.1021/jo961048r

Reference yield:

(4aS)-1,4aβ-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione-5-ethyeneacetal (26742-33-6) → (1S,4aS)-(+)-trans-1α-[(2,5-dimethoxyphenyl)methyl]-1β,4aβ-dimethyl-5-(2-methyl-1,3-dioxolan-2-yl)-2-methyleneoctahydro-5(6H)-naphthalenone (184485-47-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / Li, NH₃ / tetrahydrofuran / 3 h / -35 °C

2: 70 percent / n-BuLi / dioxane / 24 h / 110 °C

With n-butyllithium; ammonia; lithium; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1016/S0040-4039(99)00686-3

upstream raw materials:

Methyltriphenylphosphonium bromide

(1S,4aS)-(+)-trans-1α-[(2,5-dimethoxyphenyl)methyl]-1β,4aβ-dimethyl-5-(2-methyl-1,3-dioxolan-2-yl)-hexahydro-2,5(3H,6H)-naphthalenedione

Methylenetriphenylphosphorane

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

Downstream raw materials:

(-)-(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

(-)-(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

avarol

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