72640-47-2

Basic information

• Product Name: ethyl α-(benzyloximino)-β-(oxindol-3-yl)propanoate
• Synonyms: ethyl α-(benzyloximino)-β-(oxindol-3-yl)propanoate
• CAS NO: 72640-47-2
• Molecular Weight: 262.265
• Mol File: 72640-47-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: ethyl α-(benzyloximino)-β-(oxindol-3-yl)propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl α-(benzyloximino)-β-(oxindol-3-yl)propanoate(72640-47-2)
• EPA Substance Registry System: ethyl α-(benzyloximino)-β-(oxindol-3-yl)propanoate(72640-47-2)

Safety Data

• Hazardous Substances Data: 72640-47-2(Hazardous Substances Data)

Upstream product

• 7652-46-2 Ac-Cys-OMe 
• 106040-12-4 3-(ethoxycarbonyl)-4a-acetoxy-4,4a,9,9a-tetrahydro-1,2-oxazino<5,6-b>indole 

Relevant articles and documents

C(2)-Functionalized Tryptophans from 3-Acetoxyindoles and Their Possible Implication in Indole Alkaloid Biosynthesis

The acetoxyindoles 10 and 11 are efficiently converted (85percent-95percent) into the dihydro-1,2-oxazines 13 and 14, respectively, by reaction with the transient nitroso olefin 2, prepared in situ from ethyl α-(hydroxyimino)-β-bromopropanoate by base treatment.The cycloadducts 13 and 14 react efficiently with thiols or a hydride donor to yield (60-90percent) the 2-substituted tryptophan derivatives 9a-f.Selective reduction of the oxime function of the 2-(S-cysteinyl)tryptophan derivative 9d afforded 19, a derivative of tryptathionine.The sulfonium salt 22b derived from 2-(ethylthio)tryptophan derivative 9b was shown to undergo a thio-Claisen rearrangement to yield 26.This reaction supports Bycroft's proposal involving a thio-Claisen rearrangement in indole alkaloid biosynthesis.