(1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,2β,4aβ-trimethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-5(6H)-one

Base Information

• Chemical Name: (1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,2β,4aβ-trimethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-5(6H)-one
• CAS No.: 481656-25-1
• Molecular Formula: C₂₁H₃₀O₂
• Molecular Weight: 314.468
• Mol file: 481656-25-1.mol

Synonyms:(1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,2β,4aβ-trimethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-5(6H)-one

Chemical Property of (1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,2β,4aβ-trimethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-5(6H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,2β,4aβ-trimethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-5(6H)-one

There total 6 articles about (1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,2β,4aβ-trimethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-5(6H)-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: 91.0%

(1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,4aβ-dimethyl-2-methylene-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-5(6H)-one (481656-23-9) → (4aS,5R,6R,8aS)-5-(2-methoxybenzyl)-5,6,8a-(trimethyl)octahydronaphthalen-1-[2H]-one + (1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,2β,4aβ-trimethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-5(6H)-one (481656-25-1)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; triethylamine; In methanol; at 20 ℃; for 24h; under 760.051 Torr;

DOI:10.1002/ejoc.201100173

Reference yield: 80.0%

(1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,4aβ-dimethyl-2-methylene-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-5(6H)-one (481656-23-9) → (1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,2β,4aβ-trimethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-5(6H)-one (481656-25-1)

Guidance literature:

With hydrogen; triethylamine; palladium on activated charcoal; In methanol; at 20 ℃; under 760 Torr;

Reference yield:

o-Methoxybenzyl bromide (52289-93-7) → (1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,2β,4aβ-trimethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-5(6H)-one (481656-25-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 72 percent / Li; liq. NH₃ / tetrahydrofuran

2: 86 percent / t-BuOK / benzene / Heating

3: 97 percent / aq. HCl / tetrahydrofuran / 20 °C

4: 80 percent / H₂; Et₃N / 10 percent Pd/C / methanol / 20 °C / 760 Torr

With hydrogenchloride; potassium tert-butylate; ammonia; hydrogen; lithium; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; benzene;

upstream raw materials:

(1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,4aβ-dimethyl-2-methylene-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-5(6H)-one

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

o-Methoxybenzyl bromide

(1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,4aβ-dimethyl-1,4,4a,7,8,8aα-hexahydronaphthalene-2,5(3H,7H)-dione-5-ethyleneacetal

Downstream raw materials:

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

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

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

(1R,2S,4aS,5R,6S,8aS)-2-[(5β,6β-epoxy-1β,2β,4aβ,5α-tetramethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-1-yl)methyl]phenol