80510-15-2

Basic information

• Product Name: 2-Pentenoic acid,2-methyl-,(1S)-1-methylbutyl ester,(2E)-
• Synonyms: DOMINICALURE;(S)-(+)-2'-pentyl (E)-2-methyl-2-pentenoate;(S)-1-methylbutyl (E)-2-methyl-2-pentenoate;(E)-(S)-(+)-1-methylbutyl 2-methyl-2-pentenoate;(S)-(+)-1-Methylbutyl (E)-2-methyl-2-pentenoate;(+)-(1S)-1-methylbutyl (2E)-2-methylpent-2-enoate;dominicalure-I
• CAS NO: 80510-15-2
• Molecular Formula: C11H20O2
• Molecular Weight: 184.279
• Mol File: 80510-15-2.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 2-Pentenoic acid,2-methyl-,(1S)-1-methylbutyl ester,(2E)- (CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pentenoic acid,2-methyl-,(1S)-1-methylbutyl ester,(2E)- (80510-15-2)
• EPA Substance Registry System: 2-Pentenoic acid,2-methyl-,(1S)-1-methylbutyl ester,(2E)- (80510-15-2)

Safety Data

• Hazardous Substances Data: 80510-15-2(Hazardous Substances Data)

Upstream product

• 83841-91-2 (E)-2-methyl-2-pentenoyl chloride 
• 26184-62-3 (S)-2-pentanol 
• 1567-14-2 methyl (2E)-2-methyl-2-pentenoate 
• 16957-70-3 2-methylpent-2-enoic acid 

Relevant articles and documents

Green and Catalytic Synthesis of Dominicalure I, Major Component of the Aggregation Pheromone of Rhyzopertha dominica (Fabricius) (Coleoptera: Bostrichidae)

(Chemical Equation Presented). A new concise and efficient catalytic synthesis of dominicalure I, the male-produced aggregation pheromone of the grain borer Rhyzopertha dominica, is herein reported. The synthetic route was designed starting from easily available propanal through an organocatalytic key step and completed with biocatalytic procedures.

Synthetic applications of the Baylis-Hillman reaction: Simple and convenient synthesis of five important insect pheromones

A simple and convenient synthesis of five important insect pheromones by means of Baylis-Hillman adducts is described, i.e., of (2E,4S)-2,4-dimethylhex- 2-enoic acid (1), a mandibular-gland secretion of the male carpenter ant in the genus Camponotus, of (+)-(S)-manicone (2) and (+)-(S)-normanicone (3), two mandibular-gland constituents of Manica ants, and of (+)-dominicalure-I (6) and (+)-dominicalure-II (7), two aggregation pheromones of the lesser grain borer Rhyzopertha dominion (F). For the first time, the potential of the Baylis-Hillman chemistry for the stereoselective synthesis of trisubstituted olefins was successfully applied to the synthesis of these pheromone compounds.

Synthetic application of alkyl (E)-2-tributylstannyl-2-alkenoates: Selective synthesis of (S)-1-methylbutyl (E)-2-methyl-2-pentenoate, an aggregation pheromone component of Rhyzopertha dominica and Prostephanus truncatus

Stereoisomerically pure (S)-1-methylbutyl (E)-2-methyl-2-pentenoate (dominicalure-1), (S)(E)-11, an aggregation pheromone component for the lesser and the greater grain borers, has been efficiently synthesized from the main product of the palladium-catalyzed reaction between ethyl 2-pentynoate, 1a, and Bu3SnH, i.e. ethyl (E)-2-tributylstannyl-2-pentenoate, (E)-2a.