65457-77-4

Basic information

• Product Name: 2-Cyclopenten-1-one, 4-(1-methyl-1-phenylethoxy)-
• CAS NO: 65457-77-4
• Molecular Formula: C14H16O2
• Molecular Weight: 216.28
• Mol File: 65457-77-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-Cyclopenten-1-one, 4-(1-methyl-1-phenylethoxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyclopenten-1-one, 4-(1-methyl-1-phenylethoxy)-(65457-77-4)
• EPA Substance Registry System: 2-Cyclopenten-1-one, 4-(1-methyl-1-phenylethoxy)-(65457-77-4)

Safety Data

• Hazardous Substances Data: 65457-77-4(Hazardous Substances Data)

Upstream product

• 542-92-7 cyclopenta-1,3-diene 
• 80-15-9 Cumene hydroperoxide 
• 57702-56-4 cis- and trans-4-cumyloxy-2-cyclopentenol 
• 258834-26-3 cis- and trans-4-cumyloxy-2-cyclopenten-1-yl acetate 

Downstream Products

• 73448-19-8 3-(trans-3,3-dimethylbuten-1-yl)-4-cumyloxycyclopentanone 
• 86894-57-7 1β-<2α-(1-methyl-1-phenylethoxy)-4-oxocyclopentyl>-3-phenylsulfinyl-2E-propene 
• 70302-44-2 3-(trans-3-tert-butyldimethylsiloxyocten-1-yl)-4-cumyloxycyclopentanone 
• 76855-50-0 trans-1-(tert-butyldimethylsilyloxy)-3-ⁿbutyl-4-cumyloxycyclopentene 
• 65457-85-4 tert-Butyl-dimethyl-[2-methyl-3-(1-methyl-1-phenyl-ethoxy)-5,5-bis-methylsulfanyl-pentyloxy]-silane 
• 65457-82-1 5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-3-(1-methyl-1-phenyl-ethoxy)-pentanoic acid methyl ester 
• 65457-81-0 5-Hydroxy-4-methyl-3-(1-methyl-1-phenyl-ethoxy)-pentanoic acid methyl ester 
• 65457-84-3 5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-3-(1-methyl-1-phenyl-ethoxy)-pentanal 
• 99474-61-0 C₂₀H₁₉NO₈ 
• 99474-66-5 Benzoic acid (1R,2R,3S,4S)-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-4-methyl-cyclopentyl ester 
• 99474-64-3 C₂₆H₃₄O₆Si 
• 99474-65-4 Benzoic acid (1R,2S,3S,4S)-2-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-4-methyl-cyclopentyl ester 
• 99474-59-6 (1R,2R,4S,5R)-2-Methyl-4-(1-methyl-1-phenyl-ethoxy)-6-oxa-bicyclo[3.1.0]hexan-2-ol 
• 73838-47-8 (1α,3α,4β)-3-(cumyloxy)-4-(3-hydroxy-1-octynyl)cyclopentanol 

Relevant articles and documents

Chiral preparation of polyoxygenated cyclopentanoids

A series of polyoxygenated cyclopentanoids, including 2,2-dimethyl- 3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one, has been prepared in both enantiomeric forms from cyclopentadiene by employing lipase-mediated kinetic resolution as the key step. Thus, cyclopentadiene is first transformed into racemic cis-4-cumyloxycyclopent-2-en-1-ol which is resolved under transesterification conditions in the presence of lipase PS. After transformation into the corresponding tert-butyldimethylsilyl (TBS) ethers, each of the enantiomers is cis-dihydroxylated diastereoselectively from the less hindered face which is transformed into the 2,3-O-isopropylidene-1,4-di- O-protected (trans-1,2:cis-2,3:trans-3,4)-1,2,3,4-cyclopentanetetraol. Selective removal of the 1,4-protecting group gives the corresponding 2,3,4- O-protected cyclopentanols which are further transformed into the 2,3,4-O- protected cyclopentanones on oxidation without suffering β-elimination. Exposure of the cyclopentanones to warm acetic acid allows β-elimination to give rise to the dehydration product 2,2,-dimethyl-3a,6a-dihydro-4H- cyclopenta[d][1,3]dioxol-4-one having the corresponding chirality without losing their original chiral integrity.

Photochemical Cycloadditions. III. Addition of 4-Substituted 2-Cyclopentenones to Allene; Configuration Determination by Lanthanide-Induced Shift Studies

Photoaddition of 4-substituted 2-cyclopentenones to 1,2-propadiene gave mixtures of the head-to-head and head-to-tail cycloadducts in a ratio of ca. 90:10.The stereoisomeric composition was sensitive to solvent changes, as was the chemical yield of the cycloadducts.Under otherwise identical conditions the highest yields were obtained in non-polar solvents.The configurations of the cycloadducts were determined by LIS and 13C NMR studies.

Letter: A simple total synthesis of prostaglandins from 4-cumyloxy-2-cyclopentenone.

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