123326-16-9

Basic information

• Product Name: 4-Pentenoic acid, 2-acetyl-, 2-propenyl ester
• CAS NO: 123326-16-9
• Molecular Formula: C10H14O3
• Molecular Weight: 182.219
• Mol File: 123326-16-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 4-Pentenoic acid, 2-acetyl-, 2-propenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Pentenoic acid, 2-acetyl-, 2-propenyl ester(123326-16-9)
• EPA Substance Registry System: 4-Pentenoic acid, 2-acetyl-, 2-propenyl ester(123326-16-9)

Safety Data

• Hazardous Substances Data: 123326-16-9(Hazardous Substances Data)

Upstream product

• 556-56-9 allyl iodid 
• 1118-84-9 allyl acetoacetate 
• 106-95-6 allyl bromide 
• 90926-38-8 3-Allyloxy-but-2c-ensaeure-allylester 

Relevant articles and documents

Studies on the α-acetylation of δ-valerolactone and ε-caprolactone

The synthetic approach to α-acetylated δ-valero- (7a) and ε-caprolactone (7b) is reported. While 7a was isolated in 21% yield from the respective iodoester 5a by an alkylation sequence involving transesterification and Finkelstein reaction, 7b was not obtained from 5b but the dimer 8. Also transesterification and olefin ring closing metathesis (RCM) failed to prepare 7b. RCM resulted in the dimeric lactone 10, showing that the formation of 14-membered rings is favored over that of seven-membered rings. A Mukaiyama-type Claisen reaction finally gave α-acetyl lactones 7a and 7b in practically useful quantity of about 10 g (62% yield): starting lactones 13a,b were converted to silylenolethers 14a,b, which were acetylated with acetic anhydride in presence of the Lewis acid catalyst TiCl4. However, acetylation depends on the addition sequence of starting materials: if the mixture of Ac2O/TiCl4 is added to 14b, lactone 7b can be further converted to give bis-oxepanonyl ethanols 15a,b. Both compounds 15 were characterized by X-ray crystallography and NMR.

Stereochemical Control in Microbial Reduction. 9. Diastereoselective Reduction of 2-Alkyl-3-oxobutanoate with Bakers' Yeast

Bakers' yeast reduces esters of 2-alkyl-3-oxobutanoic acid (CH3COCHRCO2R'; R=methyl, ethyl, propyl, propargyl, and allyl) into the corresponding (S)-hydroxy esters with exclusive stereoselectivity, while the configuration at the 2-position of the hydroxy esters is either S (anti) or R (syn) depending on the structure of the alkoxyl group in the carboalkoxyl moeity of the ester.Oftently, the stereoselectivity with respect to the 2-position is not satisfactory.In general, the reduction of t-butyl esters exerts predominancy in the products, whereas that of 1,1-dimethylpropyl esters exerts the syn predominancy.A marked difference between these two esters in diastereoselectivity is dicussed from the view point of plausible conformations of the esters.