(1S,4R,5S)-4-(2,5-dimethoxy-4-methylphenyl)-3,3,4-trimethyl-6-oxa-bicyclo[3.1.0]hexan-2-one

Base Information

• Chemical Name: (1S,4R,5S)-4-(2,5-dimethoxy-4-methylphenyl)-3,3,4-trimethyl-6-oxa-bicyclo[3.1.0]hexan-2-one
• CAS No.: 733001-87-1
• Molecular Formula: C₁₇H₂₂O₄
• Molecular Weight: 290.359

Synonyms:(1S,4R,5S)-4-(2,5-dimethoxy-4-methylphenyl)-3,3,4-trimethyl-6-oxa-bicyclo[3.1.0]hexan-2-one

Chemical Property of (1S,4R,5S)-4-(2,5-dimethoxy-4-methylphenyl)-3,3,4-trimethyl-6-oxa-bicyclo[3.1.0]hexan-2-one

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Technology Process of (1S,4R,5S)-4-(2,5-dimethoxy-4-methylphenyl)-3,3,4-trimethyl-6-oxa-bicyclo[3.1.0]hexan-2-one

There total 2 articles about (1S,4R,5S)-4-(2,5-dimethoxy-4-methylphenyl)-3,3,4-trimethyl-6-oxa-bicyclo[3.1.0]hexan-2-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: 51.0%

(R)-4-(2,5-dimethoxy-4-methylphenyl)-2-methoxy-4,5,5-trimethylcyclopent-2-enone (733001-90-6) → (1S,4R,5S)-4-(2,5-dimethoxy-4-methylphenyl)-3,3,4-trimethyl-6-oxa-bicyclo[3.1.0]hexan-2-one (733001-87-1)

Guidance literature:

With sodium hydroxide; dihydrogen peroxide; In methanol; at 60 ℃; for 6.5h;

DOI:10.1016/j.tetlet.2004.04.191

Reference yield: 51.0%

(R)-4-(2,5-dimethoxy-4-methylphenyl)-4,5,5-trimethylcyclopent-2-en-1-one (733001-86-0) → (1S,4R,5S)-4-(2,5-dimethoxy-4-methylphenyl)-3,3,4-trimethyl-6-oxa-bicyclo[3.1.0]hexan-2-one (733001-87-1)

Guidance literature:

With sodium hydroxide; dihydrogen peroxide; In methanol; at 0 - 60 ℃;

DOI:10.1271/bbb.69.374

Reference yield: 83.0%

sodium methylate (124-41-4) + (1S,4R,5S)-4-(2,5-dimethoxy-4-methylphenyl)-3,3,4-trimethyl-6-oxa-bicyclo[3.1.0]hexan-2-one (733001-87-1) → (R)-4-(2,5-dimethoxy-4-methylphenyl)-2-methoxy-4,5,5-trimethylcyclopent-2-enone (733001-90-6)

Guidance literature:

With methanol; at 60 ℃; for 240h; regioselective reaction; Inert atmosphere;

DOI:10.1021/acs.orglett.8b02788

upstream raw materials:

(R)-4-(2,5-dimethoxy-4-methylphenyl)-2-methoxy-4,5,5-trimethylcyclopent-2-enone

(R)-4-(2,5-dimethoxy-4-methylphenyl)-4,5,5-trimethylcyclopent-2-en-1-one

Downstream raw materials:

(3R,4R)-3-(2,5-dimethoxy-4-methylphenyl)-4-hydroxy-2,2,3-trimethylcyclopentanone

(R)-4-(2,5-dimethoxy-4-methylphenyl)-2-methoxy-4,5,5-trimethylcyclopent-2-enone

2-methyl-5-[(1S,5R)-5-hydroxy-1,2,2-trimethyl-3-oxocyclopentyl]-1,4-benzoquinone

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