Acetic acid (1S,5R)-5-acetoxy-3-(2,2-dibromo-vinyl)-2-methyl-cyclohex-2-enyl ester

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Chemical Name:Acetic acid (1S,5R)-5-acetoxy-3-(2,2-dibromo-vinyl)-2-methyl-cyclohex-2-enyl ester
CAS No.:113393-82-1
Molecular Formula:C₁₃H₁₆Br₂O₄
Molecular Weight:396.076
Hs Code.:

Synonyms:Acetic acid (1S,5R)-5-acetoxy-3-(2,2-dibromo-vinyl)-2-methyl-cyclohex-2-enyl ester

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Chemical Property of Acetic acid (1S,5R)-5-acetoxy-3-(2,2-dibromo-vinyl)-2-methyl-cyclohex-2-enyl ester

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Technology Process of Acetic acid (1S,5R)-5-acetoxy-3-(2,2-dibromo-vinyl)-2-methyl-cyclohex-2-enyl ester

There total 10 articles about Acetic acid (1S,5R)-5-acetoxy-3-(2,2-dibromo-vinyl)-2-methyl-cyclohex-2-enyl 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: 72.0%

: 558-13-4
carbon tetrabromide

: 55448-87-8
(3S,5R)-3,5-Diacetoxy-2-methylcyclohex-1-ene-1-carboxaldehyde

: 113393-82-1
Acetic acid (1S,5R)-5-acetoxy-3-(2,2-dibromo-vinyl)-2-methyl-cyclohex-2-enyl ester

Guidance literature:: With pyridine; triphenylphosphine; zinc; for 1h; Ambient temperature;
DOI:10.1016/S0040-4039(00)96053-2

Reference yield:

: 2244-16-8,6485-40-1
(S)-p-mentha-6,8-dien-2-one

: 113393-82-1
Acetic acid (1S,5R)-5-acetoxy-3-(2,2-dibromo-vinyl)-2-methyl-cyclohex-2-enyl ester

Guidance literature:: Multi-step reaction with 7 steps

2: 86 percent / tert-butylhydroperoxide, / vanadyl acetyl acetonate / benzene; toluene / 3 h / Ambient temperature

3: 88 percent / OsO₄, KIO₄ / tetrahydrofuran; H₂O / 15 h / Ambient temperature

4: 89 percent / m-CPBA / CHCl₃; H₂O / 25 h / pH 7.8

5: 1.) oxalyl chloride, Me₂SO 2.)Et₃N / 1.) CH₂Cl₂, 15 min, -60 deg C 2.) 0-10 deg C, 5 h

6: 95 percent / dimethylaminopyridine, pyridine / 6 h / 25 °C

7: 1.) zinc dust, Ph₃P 2.) pyridine / 1.) CH₂Cl₂, 15 min, r.t. 2.) CH₂Cl₂, 30 min r.t.

With pyridine; tert.-butylhydroperoxide; dmap; osmium(VIII) oxide; potassium metaperiodate; oxalyl dichloride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; zinc; bis(acetylacetonate)oxovanadium; In tetrahydrofuran; chloroform; water; toluene; benzene;
DOI:10.1016/S0040-4020(01)86410-3

Reference yield:

: 113375-47-6
(1R,2S,4R,6S)-2-Hydroxymethyl-1-methyl-4-(1-methylethenyl)-7-oxybicyclo<4.1.0>heptane

: 113393-82-1
Acetic acid (1S,5R)-5-acetoxy-3-(2,2-dibromo-vinyl)-2-methyl-cyclohex-2-enyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 88 percent / OsO₄, KIO₄ / tetrahydrofuran; H₂O / 15 h / Ambient temperature

2: 89 percent / m-CPBA / CHCl₃; H₂O / 25 h / pH 7.8

3: 1.) oxalyl chloride, Me₂SO 2.)Et₃N / 1.) CH₂Cl₂, 15 min, -60 deg C 2.) 0-10 deg C, 5 h

4: 95 percent / dimethylaminopyridine, pyridine / 6 h / 25 °C

5: 1.) zinc dust, Ph₃P 2.) pyridine / 1.) CH₂Cl₂, 15 min, r.t. 2.) CH₂Cl₂, 30 min r.t.

With pyridine; dmap; osmium(VIII) oxide; potassium metaperiodate; oxalyl dichloride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; zinc; In tetrahydrofuran; chloroform; water;
DOI:10.1016/S0040-4020(01)86410-3