32346-66-0

Basic information

• Product Name: Methanone, [(1R,2S)-2-hydroxycyclopentyl]phenyl-, rel-
• CAS NO: 32346-66-0
• Molecular Formula: C12H14O2
• Molecular Weight: 190.242
• Mol File: 32346-66-0.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: Methanone, [(1R,2S)-2-hydroxycyclopentyl]phenyl-, rel-(CAS DataBase Reference)
• NIST Chemistry Reference: Methanone, [(1R,2S)-2-hydroxycyclopentyl]phenyl-, rel-(32346-66-0)
• EPA Substance Registry System: Methanone, [(1R,2S)-2-hydroxycyclopentyl]phenyl-, rel-(32346-66-0)

Safety Data

• Hazardous Substances Data: 32346-66-0(Hazardous Substances Data)

Upstream product

• 502-44-3 hexahydro-2H-oxepin-2-one 
• 34879-53-3 cis-3a,5,6,6a-Tetrahydro-3-phenyl-4H-cyclopentisoxazole 
• 87258-30-8 6-oxo-6-phenylhexanal 
• 73504-72-0 phenyl(tetrahydro-2H-pyran-2-yl)methanone 
• 108-86-1 bromobenzene 
• 17851-49-9 5-hydroxypentyl phenyl ketone 
• 58074-39-8 3-phenyl-3a,5,6,6a-tetrahydrocyclopentaisoxazoline 
• 347376-10-7 trans-6-oxo-6-phenylhex-4-enal 
• 285-67-6 Cyclopentene oxide 
• 100-47-0 benzonitrile 

Relevant articles and documents

Photomediated ring contraction of saturated heterocycles

Saturated heterocycles are found in numerous therapeutics and bioactive natural products and are abundant in many medicinal and agrochemical compound libraries. To access new chemical space and function, many methods for functionalization on the periphery of these structures have been developed. Comparatively fewer methods are known for restructuring their core framework. Herein, we describe a visible light-mediated ring contraction of a-acylated saturated heterocycles. This unconventional transformation is orthogonal to traditional ring contractions, challenging the paradigm for diversification of heterocycles including piperidine, morpholine, thiane, tetrahydropyran, and tetrahydroisoquinoline derivatives. The success of this Norrish type II variant rests on reactivity differences between photoreactive ketone groups in specific chemical environments. This strategy was applied to late-stage remodeling of pharmaceutical derivatives, peptides, and sugars.

Borinic Acid/Halide Co-catalyzed Semipinacol Rearrangements of 2,3-Epoxy Alcohols

A new mode of catalysis of the semipinacol rearrangement of 2,3-epoxy alcohols is described. In combination with a halide salt additive, diarylborinic acids promote a Type II rearrangement that occurs with net retention of configuration. This unusual stereochemical outcome is consistent with a mechanism involving regioselective ring opening of the epoxy alcohol by halide, followed by rearrangement of the resulting halohydrin-derived borinic ester. The protocol is applicable to a range of substrates, enabling ring contractions and expansions as well as stereospecific syntheses of acyclic β-hydroxycarbonyl compounds.

TBD-catalyzed direct 5- and 6-enolexo aldolization of ketoaldehydes

Treatment of unfunctionalized acyclic ketoaldehydes with a catalytic amount of 1,5,7-triazabicyclo[4.4.0]dec-5-ene induces a direct intramolecular 5- and 6-enolexo aldolization, furnishing 2-ketocyclopentanols and 2-ketocyclohexanols in good-to-excellent yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.