97309-25-6

Basic information

• Product Name: (Z)-4,5-Epoxy-3-methyl-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-pentensaeure-methylester
• Synonyms: (Z)-4,5-Epoxy-3-methyl-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-pentensaeure-methylester
• CAS NO: 97309-25-6
• Molecular Weight: 264.365
• Mol File: 97309-25-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (Z)-4,5-Epoxy-3-methyl-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-pentensaeure-methylester(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-4,5-Epoxy-3-methyl-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-pentensaeure-methylester(97309-25-6)
• EPA Substance Registry System: (Z)-4,5-Epoxy-3-methyl-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-pentensaeure-methylester(97309-25-6)

Safety Data

• Hazardous Substances Data: 97309-25-6(Hazardous Substances Data)

Upstream product

• 37079-64-4 1-[3-(2,6,6-trimethyl-cyclohex-2-enyl)-oxiranyl]-ethanone 
• 5927-18-4 trimethyl phosphonoacetate 

Downstream Products

• 97309-62-1 cis-5-Chlor-4-methyl-6-(2,6,6-trimethyl-2-cyclohexen-1-yl)-5,6-dihydro-2H-pyran-2-on 
• 97291-42-4 4-Methyl-6-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2H-pyran-2-on 
• 97309-31-4 trans-5-Hydroxy-4-methyl-6-(2,6,6-trimethyl-2-cyclohexen-1-yl)-5,6-dihydro-2H-pyran-2-on 

Relevant articles and documents

Formation and Reactivity of Hydroxy-substituted γ- and δ-Lactones

Hydrolysis of the esters (Z)-6-8 with H2SO4 in acetone leads to a mixture of γ- (17-19) and δ-Lactones (13-15) in various ratios.From (Z)-9 the rearrangement product 20 is obtained.By reaction of (Z)-6-9 with Et2O-BF3 the δ-lactones 13-16 are formed only.The saturated esters 10-12 hydrolyze to give a γ/δ-lactone mixture 24-26/21-23.Changing to BF3, favors the rearrangement 10 -> 30. - The δ-lactones 13-16 are not dehydrated with POCl3 in pyridine but chlorinated to afford 31-34.On heating in pyridine 33 and 34 are dehydrochlorinated to give the α-pyrones 38 and 39.Dechlorination with zinc in acetic acid leads to β,γ-unsaturated δ-lactones (31,35 -> 44; 32 -> 45; 33 -> 46).The mixture of saturated γ/δ-lactones 21b/24a/24b yields with POCl3 the elimination products 50 and 51, while a 23/26a/26b mixture furnishes the unsaturated γ-lactones 53a, b, and 54 as well as the chlorinated δ-lactones 55.Hydrogenation (44 -> 56; 45 -> 57; 46 -> 58; 51-> 59; 53/54 -> 60) gives the saturated parent compounds.