(E)-3-phenyl-thioprop-2-ene-oic acid (S)-ethyl ester

Base Information

• Chemical Name: (E)-3-phenyl-thioprop-2-ene-oic acid (S)-ethyl ester
• CAS No.: 108387-99-1
• Molecular Formula: C₁₁H₁₂OS
• Molecular Weight: 192.282
• Mol file: 108387-99-1.mol

Synonyms:(E)-3-phenyl-thioprop-2-ene-oic acid (S)-ethyl ester

Chemical Property of (E)-3-phenyl-thioprop-2-ene-oic acid (S)-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of (E)-3-phenyl-thioprop-2-ene-oic acid (S)-ethyl ester

There total 12 articles about (E)-3-phenyl-thioprop-2-ene-oic acid (S)-ethyl 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: 98.0%

phenylacetylene (536-74-3) + ethanethiol (75-08-1) + molybdenum hexacarbonyl (13939-06-5,199620-15-0) → (E)-3-phenyl-thioprop-2-ene-oic acid (S)-ethyl ester (108387-99-1)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; In N,N-dimethyl-formamide; at 100 ℃; regioselective reaction;

DOI:10.1016/j.jorganchem.2016.01.025

Reference yield: 96.0%

trimethylsilylethane (3439-38-1) + Methyl cinnamate (103-26-4,1754-62-7) → (E)-3-phenyl-thioprop-2-ene-oic acid (S)-ethyl ester (108387-99-1)

Guidance literature:

With aluminum (III) chloride; In tetrahydrofuran; for 3.5h; Inert atmosphere; Reflux;

DOI:10.1039/c7cc05433e

Reference yield: 89.0%

carbon monoxide (201230-82-2) + phenylacetylene (536-74-3) + ethanethiol (75-08-1) → (E)-3-phenyl-thioprop-2-ene-oic acid (S)-ethyl ester (108387-99-1)

Guidance literature:

With palladium(II) trifluoroacetate; 5-chloro-2-hydroxybenzoic acid; boric acid; bis[2-(diphenylphosphino)phenyl] ether; In acetonitrile; at 110 ℃; for 14h; under 7500.75 Torr; regioselective reaction; Autoclave;

DOI:10.1002/anie.202106079

upstream raw materials:

phenylacetylene

ethanethiol

Cinnamoyl chloride

ethylthioacetylene

Downstream raw materials:

S-ethyl 3-phenylpropionic acid thioester

3-Phenylhexanal

Refernces

• 1、 Ai, Han-Jun,Lu, Wangyang,Wu, Xiao-Feng. "Ligand-Controlled Regiodivergent Thiocarbonylation of Alkynes toward Linear and Branched α,β-Unsaturated Thioesters". supporting information. p. 17178 - 17184. Retrieved 2021/06/28.
• 2、 Iranpoor, Nasser,Firouzabadi, Habib,Riazi, Asma,Pedrood, Keyvan. "Regioselective hydrocarbonylation of phenylacetylene to α,β-unsaturated esters and thioesters with Fe(CO)5and Mo(CO)6". . p. 67 - 73. Retrieved 2016/08/30.