135923-82-9

Basic information

• Product Name: S-ethyl (E)-5-phenylpent-2-enethioate
• Synonyms: S-ethyl (E)-5-phenylpent-2-enethioate
• CAS NO: 135923-82-9
• Molecular Weight: 220.335
• Mol File: 135923-82-9.mol

Chemical Properties

• CAS DataBase Reference: S-ethyl (E)-5-phenylpent-2-enethioate(CAS DataBase Reference)
• NIST Chemistry Reference: S-ethyl (E)-5-phenylpent-2-enethioate(135923-82-9)
• EPA Substance Registry System: S-ethyl (E)-5-phenylpent-2-enethioate(135923-82-9)

Safety Data

• Hazardous Substances Data: 135923-82-9(Hazardous Substances Data)

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 3699-87-4 S-ethyl 2-(diethoxyphosphoryl) ethanethioate 
• 32443-51-9 S-ethyl 2-(triphenylphosphoranylidene)ethanethioate 

Relevant articles and documents

Stereoselective Synthesis of Baulamycin A

New structural classes of antibiotics are rare, structurally novel broad-spectrum antibiotics exceptionally so. The recently discovered baulamycins constitute a remarkable example of these highly prized compounds and, as such, have attracted considerable attention in the form of both synthetic efforts and biological studies. For the first time, we report a gram-scale preparation of the common carbon framework of the baulamycin family, as well as the total synthesis of its most potent member, baulamycin A. Our approach employs highly stereoselective, catalyst-controlled asymmetric conjugate additions to thioesters to set key stereocenters, as well as the first reported use of "dry ozonolysis" to reveal a masked carboxylic acid in the total synthesis of a natural product.

Asymmetric conjugate addition of alkylzirconium reagents to α,β-unsaturated thioesters: Access to fragrances and acyclic stereochemical arrays

Copper-catalyzed asymmetric conjugate addition of alkylzirconium species to α,β-unsaturated thioesters is reported. A variety of functionalized alkyl nucleophiles were introduced with yields around 70% and ee's over 92%. The method was applied to the straightforward syntheses of the commercially important fragrances phenoxanol (both enantiomers 97% ee), and hydroxycitronellal (98% ee). The 1,4-addition products can be converted to enantiomerically enriched linear building blocks bearing a terminal functional group. Formation of further α,β-unsaturated thioesters provides an iterative route for the stereocontrolled synthesis of functionalized acyclic arrays and we demonstrate almost complete catalyst control in the formation of additional stereocentres.

Thiol esters in organic synthesis. XVI. Formation of α,β-unsaturated thiol esters via a Wadsworth-Emmons process

α,β-Unsaturated thiol esters could be readily prepared via a Wadsworth-Emmons reaction using diethyl alkylthiocarbonylmethylphosphonate, which proved to be superior in reactivity to the corresponding Wittig reagent. Key words: α,β-unsaturated thiol esters