6932-46-3

Basic information

• Product Name: 2,4-Hexadienoic acid, methyl ester, (Z,E)-
• CAS NO: 6932-46-3
• Molecular Formula: C7H10O2
• Molecular Weight: 126.155
• Mol File: 6932-46-3.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 2,4-Hexadienoic acid, methyl ester, (Z,E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Hexadienoic acid, methyl ester, (Z,E)-(6932-46-3)
• EPA Substance Registry System: 2,4-Hexadienoic acid, methyl ester, (Z,E)-(6932-46-3)

Safety Data

• Hazardous Substances Data: 6932-46-3(Hazardous Substances Data)

Upstream product

• 123-73-9 trans-Crotonaldehyde 
• 191018-96-9 methyl 2-[bis(2,4-difluorophenoxy)phosphoryl]acetate 
• 108965-77-1 (E)-(2S,3S)-2-Hydroxy-3-trimethylsilanyl-hex-4-enoic acid methyl ester 
• 127280-96-0 Methyl (trans,E)-3-(2-Methyl-5,8-dioxaspiro<3.4>oct-1-yl)-2-propenoate 
• 127379-37-7 Methyl (trans,Z)-3-(2-Methyl-5,8-dioxaspiro<3.4>oct-1-yl)-2-propenoate 
• 127379-38-8 Methyl (cis,E)-3-(2-Methyl-5,8-dioxaspiro<3.4>oct-1-yl)-2-propenoate 
• 5927-18-4 trimethyl phosphonoacetate 
• 16695-14-0 Malonic acid monomethyl ester 
• 186581-53-3 diazomethane 
• 110-44-1 hexa-2,4-dienoic acid 

Downstream Products

• 5837-72-9 methyl (E)-4-oxo-2-butenoate 
• 40188-21-4 methyl (E,E)-5-formyl-2,4-pentadienoate 
• 142334-76-7 methyl (2Z,4E)-6-oxohexa-2,4-dienolate 
• 110318-18-8 4-Methyl-2--1,5-cyclohexadiencarbonsaeure-methylester 
• 110318-19-9 Trimethyl-1,4-diazaspiro<4.5>dec-6-en-6-carbonsaeure-methylester 
• 110434-26-9 (E)-6-(N,N'-Dimethyl-2-imidazolidinyliden)-5-methyl-3-hexensaeure-methylester 
• 110434-25-8 cis-1,4,9-Trimethyl-1,4-diazaspiro<4.5>dec-7-en-6-carbonsaeure-methylester 
• 110434-32-7 trans-1,4,9-Trimethyl-1,4-diazaspiro<4.5>dec-7-en-6-carbonsaeure-methylester 
• 110434-33-8 (E)-3-(1,3-Dimethyl-imidazolidin-2-ylidenemethyl)-hex-4-enoic acid methyl ester 
• 1516-17-2 2,4-hexadien-1-ol acetate 

Relevant articles and documents

A de novo asymmetric approach to achiral deoxy-melodorinol analogues

A short and highly efficient route to deoxy-Melodorinol analogues has been developed. The key to the overall transformation is the use of an enantioselective Sharpless asymmetric dihydroxylation of an (Z,E)-dienoate to control the regioselectivity of the dihydroxylation reaction and a Mitsunobu elimination reaction to control the E-stereochemistry of the,δ-double bond. The highly efficient synthesis stereoselectively prepared four analogues in 3 steps from 4-substituted crotonaldehydes.

Vinylcyclobutane-Cyclohexane Rearrangements: Zwitterions as Discrete Intermediates

Donor-acceptor-substituted vinylcyclobutanes 1 rearrange to cyclohexenes 2 at temperatures between 20 and 195 deg C.In solvents of low polarity, cycloreversion competes with ring enlargement.Under acidic conditions, addition of nucleophiles to vinylcyclobutanes 1 with ring opening is observed.Stereospecificity of rearrangement and cycloreversion are functions of temperature, solvent polarity and acid catalysis.Strong dependence on solvent polarity is found for the rates of both reactions.The mechanisms of the thermally induced and acid-catalyzed reactions are discussed on the basis of stereospecificity, kinetic parameters and trapping of intermediates.Two structurally different zwitterions 13 and 14 are proposed as intermediates, one of which is responsible for rearrangement, the other for diastereomerization and cycloreversion.

Stereoselective Synthesis of (2E,4E)- and (2Z,4E)-2,4-Alkadienoates by the Ester Enolate Claisen Rearrangement of (E)-1-Alkyl-3-trimethylsilyl-2-propenyl Glycolates Followed by the Peterson Reaction

The ester enolate Claisen rearrangement of (E)-1-alkyl-3-trimethylsilyl-2-propenyl glycolates gave (E)-erythro-2-hydroxy-3-trimethylsilyl-4-alkenoates with high diastereoselectivity, which were stereoselectively converted into (2E,4E)- and (2Z,4E)-2,4-alkadienoates by the Peterson reaction.