90314-47-9

Basic information

• Product Name: 3-Cyclopentene-1,2-diol, 1-ethynyl-3-methyl-, cis- (9CI)
• Synonyms: 3-Cyclopentene-1,2-diol, 1-ethynyl-3-methyl-, cis- (9CI)
• CAS NO: 90314-47-9
• Molecular Formula: C8H10O2
• Molecular Weight: 138.1638
• Mol File: 90314-47-9.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Cyclopentene-1,2-diol, 1-ethynyl-3-methyl-, cis- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Cyclopentene-1,2-diol, 1-ethynyl-3-methyl-, cis- (9CI)(90314-47-9)
• EPA Substance Registry System: 3-Cyclopentene-1,2-diol, 1-ethynyl-3-methyl-, cis- (9CI)(90314-47-9)

Safety Data

• Hazardous Substances Data: 90314-47-9(Hazardous Substances Data)

Upstream product

• 17024-44-1 2,3-epoxy-3-methylcyclopentanone 
• 4301-14-8 acetylenemagnesium bromide 
• 90314-53-7 cis-2,3-epoxy-1-ethynyl-3-methylcyclopentanol 

Relevant articles and documents

Reaction of Grignard reagents with α-epoxycyclopentanones. II. The opening of the oxirane ring

By reaction of ethyl-, vinyl- and ethynylmagnesium bromides with 2,3-epoxycyclopentanone 1 at -70 deg C and heating of the reaction mixture at 40 deg C, the epoxycyclopentanols 3 were obtained only in trace amounts, whereas the bromodiols 5 formed in higher than 75percent isolated yields.The presence of cis-vicinal diol in all bromodiols is clear from the obtention of O-isopropylidene derivatives 6.In the same conditions as for epoxycyclopentanone 1, the epoxyketone 2 reacted in a much different way, giving hydroxycyclopentanones 7 (50-60percent), cyclopentendiols 8 (18-37percent) and methylidenecyclopentanediols 9 (small to trace amounts).When an excess of the ethyl- or ethynylmagnesium bromide was used, epoxycyclopentanone 2 gave the dialkyldiols 10a (58percent) and 10c (62percent).The configuration of the cyclopentenediol 8a was determined by preparation of the O-isopropylidene derivative.For the other products we have made the assignment taking into account negative experiments and mechanistic considerations.