132592-41-7

Basic information

• Product Name: (Z)-1-phenyl-1,4-pentadien-3-yl 2,2-dimethylpropanoate
• Synonyms: (Z)-1-phenyl-1,4-pentadien-3-yl 2,2-dimethylpropanoate
• CAS NO: 132592-41-7
• Molecular Weight: 244.334
• Mol File: 132592-41-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (Z)-1-phenyl-1,4-pentadien-3-yl 2,2-dimethylpropanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-1-phenyl-1,4-pentadien-3-yl 2,2-dimethylpropanoate(132592-41-7)
• EPA Substance Registry System: (Z)-1-phenyl-1,4-pentadien-3-yl 2,2-dimethylpropanoate(132592-41-7)

Safety Data

• Hazardous Substances Data: 132592-41-7(Hazardous Substances Data)

Upstream product

• 588-73-8 (Z)-β-bromostyrene 
• 3282-30-2 pivaloyl chloride 
• 107-02-8 acrolein 

Downstream Products

• 1718-50-9 1,5-diphenylpentane 
• 26057-47-6 (Z,Z)-1,5-diphenyl-1,3-pentadiene 
• 26057-47-6 (1E,4Z)-1,5-diphenyl-1,4-pentadiene 
• 73062-33-6 (1E,4E)-nona-1,4-diene-1-ylbenzene 
• 60835-95-2 (Z,E)-1-phenyl-1,3-nonadiene 
• 1081-77-2 n-nonylbenzene 

Relevant articles and documents

Alkylation of Allylic Derivatives. 17. Cross-Coupling Reactions of Diallylic Pivalates with Butyl- and Phenylcopper Reagents

Cross coupling (Z)-1-phenyl-1,4-pentadien-3-yl pivalate (cis-1-OPiv) with LiCuBu2, LiCu(CN)Bu, LiCuPh2 and LiCu(CN)Ph gives only the fully conjugated γ-coupling product.With LiCuBr2 substantial loss of double-bond configuration occures to give primarily the all-trans coupling product.With other cuprates, no detectable loss of double-bond configuration was observed.Cross coupling (Z)-3-(2-phenylethenyl)-2-cyclohexen-yl pivalate (cis-18-OPiv) with LiCuBu2, LiCuPh2, and LiCu(CN)Ph gives only α coupling product; with LiCu(CN)Bu, a mixture of α, γ, and ε coupling product was obtained.Cross coupling with LiCuBu2 results in loss of double-bond configuration in the α-alkylation product.With other cuprates, no loss of double-bond configuratiuon was detected in the α and γ coupling product.These results have profound mechanistic implications, which are discussed.The relationship between structure and reactivity was also investigated.A variety of diallylic pivalates (1-5-OPiv) were prepared and cross coupled with LiCuBu2, LiCu(CN)Bu, LiCuPh2, and LiCu(CN)Ph.Generally, coupling occurs at the least-substituted allylic system; mechanistic implications are discussed.