70329-63-4

Basic information

• Product Name: (+/-)-5,6-dehydrosenedigitalene
• Synonyms: (+/-)-5,6-dehydrosenedigitalene
• CAS NO: 70329-63-4
• Molecular Weight: 188.313
• Mol File: 70329-63-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (+/-)-5,6-dehydrosenedigitalene(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-5,6-dehydrosenedigitalene(70329-63-4)
• EPA Substance Registry System: (+/-)-5,6-dehydrosenedigitalene(70329-63-4)

Safety Data

• Hazardous Substances Data: 70329-63-4(Hazardous Substances Data)

Upstream product

• 21889-88-3 hept-6-en-2-one 
• 106-38-7 para-bromotoluene 
• 1119-51-3 bromopentene 
• 75227-09-7 2-(3-p-Tolyl-butyl)-malonic acid diethyl ester 
• 75227-10-0 2-(3-p-Tolyl-butyl)-malonic acid monoethyl ester 
• 83912-17-8 Ethyl 5-hydroxy-5-(p-tolyl)hexanoate 
• 75227-11-1 Ethyl 5-(p-tolyl)hexanoate 
• 28591-18-6 5-(4-methylphenyl)hexan-1-ol 
• 4761-26-6 ethyl 2-carbethoxy-5-oxocaproate 
• 13984-57-1 ethyl 5-oxohexanoate 
• 64841-44-7 5-<2'-(tetrahydropyranyloxy)>-1-pentene 
• 78518-93-1 5-(p-Tolyl)-hexanal 
• 19493-09-5 Methylenetriphenylphosphorane 

Relevant articles and documents

Synthesis of (Z)-6-heneicosen-11-one, (+/-)(Z)-14-methyl-8-hexadecen-1-ol and (+/-)-5,6-dehydrosenedigitalene

Three naturally occurring compounds (Z)-6-heneicosen-11-one (1), (+/-)-(Z)-14-methyl-8-hexadecen-1-ol (2) and (+/-)-5,6-dehydrosenedigitalene (3) have been synthesised using lithium tetrachlorocuperate catalysed coupling reaction.

A New Synthesis of (+/-)-5,6-Dehydrosenedigitalene

Ethyl 2-carbethoxy-5-oxohexanoate (II) on heating with NaCl in DMSO-water mixture gives the monoester (III) which when submitted to selective Grignard reaction with p-tolylmagnesium bromide furnishes ethyl 5-hydroxy-5-(p-tolyl)hexanoate (IV).The benzylic alcohol (IV) on catalytic hydrogenolysis gives ethyl 5-(p-tolyl)hexanoate (V) which on reduction with LAH provides the alcohol (VI).Oxidation of VI with Corey's reagent furnishes the aldehyde (VII) which on Wittig reaction with methylenetriphenylphosphorane in DMSO yields the title compound (I).