(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

Base Information

• Chemical Name: (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
• CAS No.: 184485-46-9
• Molecular Formula: C₂₃H₃₂O₅
• Molecular Weight: 388.504
• Mol file: 184485-46-9.mol

Synonyms:(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

Chemical Property of (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

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)-hexahydro-2,5(3H,6H)-naphthalenedione

There total 4 articles about (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 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: 98.0%

(4aS)-1,4aβ-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione-5-ethyeneacetal (26742-33-6) + 2,5-dimethoxybenzyl bromide (60732-17-4) → (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)

Guidance literature:

With ammonia; lithium;

DOI:10.1039/CC9960002717

Reference yield:

(S)-1,4a-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione (41722-49-0) → (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)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / 2-ethyl-2-methyl-1,3-dioxolane, D-CSA / 3 h / 60 °C

2: 80 percent / Li, NH₃ / tetrahydrofuran / 3 h / -35 °C

With 2-ethyl-2-methyl-1,3-dioxolane; (1S)-10-camphorsulfonic acid; ammonia; lithium; In tetrahydrofuran;

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

Reference yield:

(8aS)-1,1-(1,2-ethylenedioxy)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-6-oxonaphthalene (61950-54-7) → (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)

Guidance literature:

Multi-step reaction with 2 steps

1: 34 percent / NaH / dimethylsulfoxide / 5 h / Ambient temperature

2: 81 percent / Li, NH₃(liquid) / tetrahydrofuran / 1.) -78 deg C to reflux; reflux, 1 h, 2.) reflux, 2 h

With ammonia; lithium; sodium hydride; In tetrahydrofuran; dimethyl sulfoxide;

DOI:10.1021/jo961048r

upstream raw materials:

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

2,5-dimethoxybenzyl bromide

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

2,5-dimethoxybenzyl alcohol

Downstream raw materials:

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

(4aS,5S,8aS)-5-(2,5-Dimethoxy-benzyl)-5,8a-dimethyl-6-methylene-octahydro-naphthalen-1-one

(-)-(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