(Z)-4-Phenylsulfanyl-hexa-3,5-dienoic acid 3-formyl-2,4,4-trimethyl-cyclohex-2-enyl ester

Base Information

Chemical Name:(Z)-4-Phenylsulfanyl-hexa-3,5-dienoic acid 3-formyl-2,4,4-trimethyl-cyclohex-2-enyl ester
CAS No.:84132-53-6
Molecular Formula:C₂₂H₂₆O₃S
Molecular Weight:370.513
Hs Code.:

Synonyms:(Z)-4-Phenylsulfanyl-hexa-3,5-dienoic acid 3-formyl-2,4,4-trimethyl-cyclohex-2-enyl ester

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Chemical Property of (Z)-4-Phenylsulfanyl-hexa-3,5-dienoic acid 3-formyl-2,4,4-trimethyl-cyclohex-2-enyl ester

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Technology Process of (Z)-4-Phenylsulfanyl-hexa-3,5-dienoic acid 3-formyl-2,4,4-trimethyl-cyclohex-2-enyl ester

There total 6 articles about (Z)-4-Phenylsulfanyl-hexa-3,5-dienoic acid 3-formyl-2,4,4-trimethyl-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: 63.0%

: 60078-92-4,14393-38-5
2,4,4-trimethyl-3-formyl-2-cyclohexen-1-ol

: 84132-29-6
(Z)-4-(phenylthio)-3,5-hexadienoic acid

: 84132-53-6
(Z)-4-Phenylsulfanyl-hexa-3,5-dienoic acid 3-formyl-2,4,4-trimethyl-cyclohex-2-enyl ester

Guidance literature:: With dicyclohexyl-carbodiimide; In tetrahydrofuran; 1.) 24 h, 0 deg C, 2.) 24 h, 25 deg C;
DOI:10.1021/jo00152a012

Reference yield:

: 84132-39-8
ethyl 4-(phenylthio)-2,4-hexadienoate

: 84132-53-6
(Z)-4-Phenylsulfanyl-hexa-3,5-dienoic acid 3-formyl-2,4,4-trimethyl-cyclohex-2-enyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / KOH / methanol / 12 h / 25 °C

2: 1.) diisopropylamine, sec-Bu-Li, 2.) HMPA / 1.) THF, cyclohexane, 30 min, -78 deg C; 2.) THF, 2 h, -78 deg C

3: 63 percent / DCC / tetrahydrofuran / 1.) 24 h, 0 deg C, 2.) 24 h, 25 deg C

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; sec.-butyllithium; diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol;
DOI:10.1021/jo00152a012

Reference yield:

: 84132-37-6
ethyl (2E,4SR,5RS)-5-hydroxy-4-(phenylthio)-2-hexenoate

: 84132-53-6
(Z)-4-Phenylsulfanyl-hexa-3,5-dienoic acid 3-formyl-2,4,4-trimethyl-cyclohex-2-enyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 50 percent / methanesulfonyl chloride / triethylamine / 18 h / 25 °C

2: 100 percent / KOH / methanol / 12 h / 25 °C

3: 1.) diisopropylamine, sec-Bu-Li, 2.) HMPA / 1.) THF, cyclohexane, 30 min, -78 deg C; 2.) THF, 2 h, -78 deg C

4: 63 percent / DCC / tetrahydrofuran / 1.) 24 h, 0 deg C, 2.) 24 h, 25 deg C

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; sec.-butyllithium; methanesulfonyl chloride; diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; triethylamine;
DOI:10.1021/jo00152a012