29526-96-3

Basic information

• Product Name: 1-PHENYL-1-CYCLOPROPANOL
• Synonyms: 1-PHENYL-1-CYCLOPROPANOL;1-Phenylcyclopropanol
• CAS NO: 29526-96-3
• Molecular Formula: C₉H₁₀O
• Molecular Weight: 134.1751
• Mol File: 29526-96-3.mol
• Article Data: 49

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-PHENYL-1-CYCLOPROPANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1-PHENYL-1-CYCLOPROPANOL(29526-96-3)
• EPA Substance Registry System: 1-PHENYL-1-CYCLOPROPANOL(29526-96-3)

Safety Data

• Hazardous Substances Data: 29526-96-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron, 52, p. 1953, 1996 DOI: 10.1016/0040-4020(95)01039-4Tetrahedron Letters, 27, p. 3243, 1986 DOI: 10.1016/S0040-4039(00)84764-4

Upstream product

• 74-96-4 ethyl bromide 
• 93-89-0 benzoic acid ethyl ester 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 75-11-6 diiodomethane 
• 4636-16-2 iodoacetophenone 
• 774-65-2 benzoic acid tert-butyl ester 
• 7269-35-4 S-(n-butyl) benzothioate 
• 1052762-47-6 lithium 1-phenylethenolate 
• 539-74-2 Ethyl 3-bromopropionate 
• 925-90-6 ethylmagnesium bromide 
• 29636-75-7 3-bromo-1-phenylpropan-1-one 
• 38858-73-0 1-phenyl-1-trimethylsiloxycyclopropane 
• 24070-51-7 β-iodopropiophenone 
• 623-71-2 ethyl 3-chloropropanoate 

Downstream Products

• 5650-41-9 3-hydroxy-1-phenylpropan-1-one 
• 38858-73-0 1-phenyl-1-trimethylsiloxycyclopropane 
• 6303-82-8 1-phenylhexane-1,5-dione 
• 6263-83-8 1,5-diphenyl-1,5-pentanedione 
• 47074-06-6 2-Methyl-1,5-diphenyl-1,5-pentanedione 
• 136068-03-6 1-phenyl-6-undecyne-1,5-dione 
• 136068-04-7 S-phenyl 5-oxo-5-phenylpentanethioate 
• 29636-75-7 3-bromo-1-phenylpropan-1-one 
• 93-55-0 1-phenyl-propan-1-one 
• 3375-38-0 1,4-dibenzoylbutane 
• 28353-03-9 6-oxo-6-phenylhexanenitrile 
• 21876-11-9 6-oxo-6-phenyl-hexanoic acid methyl ester 
• 29526-97-4 1-methoxy-1-phenylcyclopropane 
• 40122-44-9 3-(9-Hydroxy-9H-fluoren-9-yl)-1-phenyl-propan-1-one 

Relevant articles and documents

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Rh-Catalyzed cascade C-H activation/C-C cleavage/cyclization of carboxylic acids with cyclopropanols

Merging both C-H and C-C activation in a tandem process is a marked challenge. A novel Rh(iii)-catalyzed C-H activation/ring opening C-C cleavage/cyclization of carboxylic acids with cyclopropanols was developed for the synthesis of 3-substituted phthalides andα,β-butenolides. This reaction displays excellent functional group tolerance with respect to both carboxylic acids and cyclopropanols and features relatively mild conditions. Remarkably, the utility of this method was highlighted by the rapid construction of bioactive compounds bearing a 3-substituted phthalide frameworkvialate-stage functionalization.

Catalytic Asymmetric Allylic Substitution with Copper(I) Homoenolates Generated from Cyclopropanols

By using copper(I) homoenolates as nucleophiles, which are generated through the ring-opening of 1-substituted cyclopropane-1-ols, a catalytic asymmetric allylic substitution with allyl phosphates is achieved in high to excellent yields with high enantioselectivity. Both 1-substituted cyclopropane-1-ols and allylic phosphates enjoy broad substrate scopes. Remarkably, various functional groups, such as ether, ester, tosylate, imide, alcohol, nitro, and carbamate are well tolerated. Moreover, the present method is nicely extended to the asymmetric construction of quaternary carbon centers. Some control experiments argue against a radical-based reaction mechanism and a catalytic cycle based on a two-electron process is proposed. Finally, the synthetic utilities of the product are showcased by means of the transformations of the terminal olefin group and the ketone group.