66618-64-2

Basic information

• Product Name: methyl (2Z)-hept-2-enoate
• CAS NO: 66618-64-2
• Molecular Formula: C₈H₁₄O₂
• Molecular Weight: 142.1956
• Mol File: 66618-64-2.mol

Chemical Properties

• Boiling Point: 172.6°C at 760 mmHg
• Flash Point: 62.3°C
• Density: 0.901g/cm³
• Vapor Pressure: 1.32mmHg at 25°C
• Refractive Index: 1.432
• CAS DataBase Reference: methyl (2Z)-hept-2-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (2Z)-hept-2-enoate(66618-64-2)
• EPA Substance Registry System: methyl (2Z)-hept-2-enoate(66618-64-2)

Safety Data

• Hazardous Substances Data: 66618-64-2(Hazardous Substances Data)

Upstream product

• 201230-82-2 carbon monoxide 
• 107574-36-7 (2E)-hex-2-en-1-yl methyl carbonate 
• 109-72-8 n-butyllithium 
• 100-39-0 benzyl bromide 
• 184377-59-1 E-2-carbomethoxyethenyl p-tolyl sulfoxide 
• 74-88-4 methyl iodide 

Downstream Products

• 100340-45-2 Z-dimethylphenylsilyloxy-1 methoxy-1 heptene-1 
• 875927-08-5 (R)-3-{(R)-1-Cyano-1-[((4S,5S)-2,2-dimethyl-4-phenyl-[1,3]dioxan-5-yl)-methyl-amino]-propyl}-heptanoic acid methyl ester 
• 124686-38-0 (R)-3-{(R)-Cyano-[((4S,5S)-2,2-dimethyl-4-phenyl-[1,3]dioxan-5-yl)-methyl-amino]-furan-2-yl-methyl}-heptanoic acid methyl ester 
• 54004-30-7 (E)-methyl hept-3-enoate 
• 100340-46-3 Z-methoxy-1 triphenylsilyloxy-1 heptene-1 
• 158849-22-0 (R)-3-aminoheptanoic acid 
• 161596-37-8 (S)-β-n-butyl-β-alanine 
• 7367-81-9 methyl (E)-oct-2-enoate 
• 2396-85-2 methyl oct-2-enoate 
• 99439-79-9 (S)-(-)-methyl 3-methylheptanoate 

Relevant articles and documents

Nucleophilic attack of 2-sulfinyl acrylates: A mild and general approach to sulfenic acid anions

An increasing number of reactions of sulfenic acid anions are being demonstrated in the literature. As such, mild, general and reliable means for the generation of sulfenates are due. In the current paper, an addition/elimination of 2-sulfinyl acrylates using various nucleophiles is demonstrated and evaluated as a protocol for alkane- and arenesulfenate generation. Cyclohexanethiolate, methoxide and n-butyllithum each exhibit some merit for the reaction, and the thiolate is established as a mild, selective and effective reagent to release sulfenates from 2-sulfinyl acrylates. The stereospecificity of the addition/elimination of each nucleophile is recognized, and an explanation for the specificity is offered for thiolate and methoxide.

Ruthenium Complex-Catalyzed Carbonylation of Allylic Compounds

Allylic alkyl carbonates are carbonylated under 40 atm of carbon monoxide at 100-120 deg C in the presence of a catalytic amount of Ru3(CO)12/1,10-phenanthroline to give α,β- or β,γ-unsaturated esters in good to high yields.For example, cinnamyl methyl carbonate afforded the corresponding β,γ-unsaturated esters, methyl trans-4-phenyl-3-butenoate (1) in 93percent yield.The regioselectivity in the carbonylation of crotyl methyl carbonate is unusual and it depends on the carbon monoxide pressure.The more sterically hindered carbon (γ-carbon) is predominantly carbonylated at 20-50 atm.When the reaction of cinnamyl methyl carbonate was performed at elevated temperature (150 deg C) without 1,10-phenanthroline, the dimer of 1, dimethyl 3-benzyl-2-(trans-2-phenylvinyl)glutarate, was obtained in 56percent yield.In the presence of secondary amines, allylic alkyl carbonates were carbonylated mainly at α-carbon to give α,β- or β,γ-unsaturated amides in high yields.

A convenient route for the homologation of saturated esters to α,β-unsaturated esters

Methyl hexanoate (1a) is transformed to methyl 2-hydroxyheptanoate (5a) employing the following sequence of reactions (Scheme 1); (i) reaction with sodium hydride-dimethyl sulfoxide, (ii) Pummerer rearrangement with acetic anhydride-sodium acetate, (iii) alkaline hydrolysis and (iv) esterification with diazomethane.The α-hydroxy ester (5a) is converted into methyl 2E-heptenoate (7a) employing the following reactions (Scheme 2); (i) reaction with phosphorous tribromide and (ii) elimination using DBU.Thus, the sequence of reactions given in Schemes 1 and 2 provide aconvenient route for the one carbon homologation of saturated esters to α,β-unsaturated esters.