106040-19-1

Basic information

• Product Name: 1H-Indole-3-propanoic acid, 2-(ethylthio)-a-[(phenylmethoxy)imino]-, ethyl ester
• CAS NO: 106040-19-1
• Molecular Formula: C22H24N2O3S
• Molecular Weight: 396.51
• Mol File: 106040-19-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1H-Indole-3-propanoic acid, 2-(ethylthio)-a-[(phenylmethoxy)imino]-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-3-propanoic acid, 2-(ethylthio)-a-[(phenylmethoxy)imino]-, ethyl ester(106040-19-1)
• EPA Substance Registry System: 1H-Indole-3-propanoic acid, 2-(ethylthio)-a-[(phenylmethoxy)imino]-, ethyl ester(106040-19-1)

Safety Data

• Hazardous Substances Data: 106040-19-1(Hazardous Substances Data)

Upstream product

• 106040-12-4 3-(ethoxycarbonyl)-4a-acetoxy-4,4a,9,9a-tetrahydro-1,2-oxazino<5,6-b>indole 
• 127033-04-9 ethyl (2Z)-3-bromo-2-(hydroxyimino)propanoate 
• 608-08-2 3-indoxyl acetate 
• 100-39-0 benzyl bromide 
• 106040-08-8 ethyl α-(hydroxyimino)-β-<2-(ethylthio)indol-3-yl>propanoate 

Downstream Products

• 106040-16-8 ethyl α-(benzyloximino)-β-<2-(ethylthio)-3-(3-methyl-2-butenyl)indolen-3-yl>propanoate 
• 106063-02-9 ethyl α-(benzyloximino)-β-<2-(ethylthio)-N-(3-methyl-2-butenyl)indol-3-yl>propanoate 
• 106040-18-0 ethyl α-(benzyloximino)-β-<2-(ethylthio)-3-(1,1-dimethyl-2-propenyl)indolen-3-yl>propanoate 

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.