(S,E)-methyl 2-(4-(4-bromobenzylidene)-1-methyl-5-oxocyclopent-2-enyl)acetate

Base Information

Chemical Name:(S,E)-methyl 2-(4-(4-bromobenzylidene)-1-methyl-5-oxocyclopent-2-enyl)acetate
CAS No.:1355677-02-9
Molecular Formula:C₁₆H₁₅BrO₃
Molecular Weight:335.197
Hs Code.:

Synonyms:(S,E)-methyl 2-(4-(4-bromobenzylidene)-1-methyl-5-oxocyclopent-2-enyl)acetate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (S,E)-methyl 2-(4-(4-bromobenzylidene)-1-methyl-5-oxocyclopent-2-enyl)acetate

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Technology Process of (S,E)-methyl 2-(4-(4-bromobenzylidene)-1-methyl-5-oxocyclopent-2-enyl)acetate

There total 5 articles about (S,E)-methyl 2-(4-(4-bromobenzylidene)-1-methyl-5-oxocyclopent-2-enyl)acetate 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: 92.0%

: 1355676-77-5
(2E,4Z,6E)-methyl 6-formyl-3-methyl-7-phenylhepta-2,4,6-trienoate

: 1355677-02-9
(S,E)-methyl 2-(4-(4-bromobenzylidene)-1-methyl-5-oxocyclopent-2-enyl)acetate

Guidance literature:: With (5aS,10bR)-5a,10b-dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride; sodium acetate; acetic acid; In diethyl ether; at 22 ℃; optical yield given as %ee; enantioselective reaction; Inert atmosphere; Darkness;
DOI:10.1021/ol203375y

Reference yield:

: 1355677-69-8
(Z)-1-bromo-4-(3,3-diethoxy-2-iodoprop-1-enyl)benzene

: 1355677-02-9
(S,E)-methyl 2-(4-(4-bromobenzylidene)-1-methyl-5-oxocyclopent-2-enyl)acetate

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / diethyl ether; hexane / 0.17 h / -78 °C

1.2: 2 h / -78 °C

1.3: 6 h / -80 - -40 °C / Inert atmosphere

2.1: hydrogenchloride; water / acetonitrile / 0.17 h / Cooling with ice

3.1: (5aS,10bR)-5a,10b-dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride; sodium acetate; acetic acid / diethyl ether / 22 °C / Inert atmosphere; Darkness

With hydrogenchloride; n-butyllithium; (5aS,10bR)-5a,10b-dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride; water; sodium acetate; acetic acid; In diethyl ether; hexane; acetonitrile; 1.3: Liebeskind-modified Stille coupling / 3.1: Stetter cyclization;
DOI:10.1021/ol203375y

Reference yield:

: C₂₀H₂₅BrO₄

: 1355677-02-9
(S,E)-methyl 2-(4-(4-bromobenzylidene)-1-methyl-5-oxocyclopent-2-enyl)acetate

Guidance literature:: Multi-step reaction with 2 steps

1: hydrogenchloride; water / acetonitrile / 0.17 h / Cooling with ice

2: (5aS,10bR)-5a,10b-dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride; sodium acetate; acetic acid / diethyl ether / 22 °C / Inert atmosphere; Darkness

With hydrogenchloride; (5aS,10bR)-5a,10b-dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride; water; sodium acetate; acetic acid; In diethyl ether; acetonitrile; 2: Stetter cyclization;
DOI:10.1021/ol203375y