80510-16-3

Basic information

• Product Name: Dominicalure 2
• CAS NO: 80510-16-3
• Molecular Weight: 198.305
• Mol File: 80510-16-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Dominicalure 2(CAS DataBase Reference)
• NIST Chemistry Reference: Dominicalure 2(80510-16-3)
• EPA Substance Registry System: Dominicalure 2(80510-16-3)

Safety Data

• Hazardous Substances Data: 80510-16-3(Hazardous Substances Data)

Upstream product

• 26184-62-3 (S)-2-pentanol 
• 89609-13-2 (E)-2,4-Dimethyl-2-pentenoic acid chloride 
• 3876-52-6 (E)-2,4-dimethylpent-2-enoic acid 

Relevant articles and documents

A facile Zn-mediated stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes from Baylis-Hillman adducts in water and its application

A simple and efficient stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes has been accomplished by treatment of the acetyl derivatives of the Baylis-Hillman adducts with Zn in saturated aq. NH 4C1 solution under reflux. The method has been utilized for the preparation of the two chiral insect pheromones, dominicalure-I and dominicalure-II, of the lesser grain borer Rhyzopertha dominica (F). Copyright

Synthesis of derivatives of (S)-2-alkanols, components of pheromones of Drosophila mulleri and Rhyzopertha dominica, from (S)-(+)-3,7-dimethylocta-1,6-diene

Effective routes for the synthesis of (S)-2-acetoxytridecane, the sex pheromone of the fruit fly Drosophila mulleri, and (S)-1-methylbutyl 2-methyl- and 2,4-dimethylpent-2E-enoates, components of the aggregation pheromone of the lesser grain borer Rhyzopertha dominica, were developed on the basis of (S)-4-methylhex-5-en-1-yl tosylate accessible from (S)-(+)-dihydromyrcene.

EFFECTIVE SYNTHESIS OF ENANTIOMERIC 2-PENTANOLS AND CHIRAL DOMINICALURES BASED ON THEM

The (S) and (R) enantiomers of sec-amyl-2-methyl-(2E)-pentenoate and 2,4-dimethyl-(2E)-pentenoate (dominicalure 1 and dominicalure 2 respectively), which are contained in the aggregation pheromone of the lesser grain borer Rhizopertha dominica, were synthesized by the acylation of (S)- and (R)-2-pentanols. (2S)-Pentanol was obtained in five stages with an overall yield of > 50percent from (S)-ethyl lactate with cross-coupling of the p-toluenesulfonate of (2S)-(2-tetrahydropyranyloxy)-1-propanol with lithium diethylcuprate at the key stage.Zinc chloride can be used as an effective catalyst for the removal of the tetrahydropyranyl protection under mild conditions. (2R)-Pentanol was prepared by inversion of the configuration of its (S) enantiomer by the Mitsunobu method.