106040-17-9

Basic information

• Product Name: ethyl α-(benzyloximino)-β-<2-((3-methyl-2-butenyl)thio)-3-(3-methyl-2-butenyl)indolen-3-yl>propanoate
• CAS NO: 106040-17-9
• Molecular Weight: 504.693
• Mol File: 106040-17-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: ethyl α-(benzyloximino)-β-<2-((3-methyl-2-butenyl)thio)-3-(3-methyl-2-butenyl)indolen-3-yl>propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl α-(benzyloximino)-β-<2-((3-methyl-2-butenyl)thio)-3-(3-methyl-2-butenyl)indolen-3-yl>propanoate(106040-17-9)
• EPA Substance Registry System: ethyl α-(benzyloximino)-β-<2-((3-methyl-2-butenyl)thio)-3-(3-methyl-2-butenyl)indolen-3-yl>propanoate(106040-17-9)

Safety Data

• Hazardous Substances Data: 106040-17-9(Hazardous Substances Data)

Upstream product

• 106040-12-4 3-(ethoxycarbonyl)-4a-acetoxy-4,4a,9,9a-tetrahydro-1,2-oxazino<5,6-b>indole 
• 106040-09-9 ethyl α-(hydroxyimino)-β-<2-((3-methyl-2-butenyl)thio)indol-3-yl>propanoate 
• 127033-04-9 ethyl (2Z)-3-bromo-2-(hydroxyimino)propanoate 
• 100-39-0 benzyl bromide 
• 608-08-2 3-indoxyl acetate 
• 106040-20-4 2-[(Z)-Benzyloxyimino]-3-[2-(3-methyl-but-2-enylsulfanyl)-1H-indol-3-yl]-propionic acid ethyl ester 
• 74-88-4 methyl iodide 

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.