5-Methyl-6-methylene-2-oxo-bicyclo[3.2.1]octane-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester

Base Information

• Chemical Name: 5-Methyl-6-methylene-2-oxo-bicyclo[3.2.1]octane-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester
• CAS No.: 144764-75-0
• Molecular Formula: C₂₃H₂₈O₃
• Molecular Weight: 352.474

Synonyms:5-Methyl-6-methylene-2-oxo-bicyclo[3.2.1]octane-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester

Chemical Property of 5-Methyl-6-methylene-2-oxo-bicyclo[3.2.1]octane-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester

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Technology Process of 5-Methyl-6-methylene-2-oxo-bicyclo[3.2.1]octane-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester

There total 4 articles about 5-Methyl-6-methylene-2-oxo-bicyclo[3.2.1]octane-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester 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: 89.0%

2-Allyl-6-methyl-3-oxo-hept-6-enoic acid (1S,2R)-2-phenyl-cyclohexyl ester (144764-70-5) → 5-Methyl-6-methylene-2-oxo-bicyclo[3.2.1]octane-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester (144764-75-0)

Guidance literature:

With copper diacetate; manganese triacetate; In acetic acid;

DOI:10.1016/S0040-4039(00)61089-4

Reference yield:

trans-2-Phenylcyclohexanol (2362-61-0) → 5-Methyl-6-methylene-2-oxo-bicyclo[3.2.1]octane-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester (144764-75-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / 4-(dimethylamino)pyridine / toluene / 120 h / Heating

2: 89 percent / Mn(OAc)3*2H₂O, Cu(OAc)2*H₂O / acetic acid / Ambient temperature

With dmap; copper diacetate; manganese triacetate; In acetic acid; toluene;

DOI:10.1021/jo00079a006

Reference yield:

methyl 2-(2-propenyl)-3-oxo-6-methylhept-6-enoate (111086-19-2) → 5-Methyl-6-methylene-2-oxo-bicyclo[3.2.1]octane-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester (144764-75-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / 4-(dimethylamino)pyridine / toluene / 120 h / Heating

2: 89 percent / Mn(OAc)3*2H₂O, Cu(OAc)2*H₂O / acetic acid / Ambient temperature

With dmap; copper diacetate; manganese triacetate; In acetic acid; toluene;

DOI:10.1021/jo00079a006

upstream raw materials:

2-Allyl-6-methyl-3-oxo-hept-6-enoic acid (1S,2R)-2-phenyl-cyclohexyl ester

trans-2-Phenylcyclohexanol

methyl 2-(2-propenyl)-3-oxo-6-methylhept-6-enoate

ethyl 2-allyl-6-methyl-3-oxo-6-heptenoate

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