14113-94-1

Basic information

• Product Name: Phenylacetylcyclopropane
• Synonyms: 1-Cyclopropyl-2-phenylethanone;Benzylcyclopropyl ketone;Cyclopropylbenzyl ketone;Phenylacetylcyclopropane
• CAS NO: 14113-94-1
• Molecular Formula: C₁₁H₁₂O
• Molecular Weight: 160.21
• Mol File: 14113-94-1.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 124 °C(Press: 10 Torr)
• Appearance: /
• Density: 1.103±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Phenylacetylcyclopropane(CAS DataBase Reference)
• NIST Chemistry Reference: Phenylacetylcyclopropane(14113-94-1)
• EPA Substance Registry System: Phenylacetylcyclopropane(14113-94-1)

Safety Data

• Hazardous Substances Data: 14113-94-1(Hazardous Substances Data)

Usage

Description

Phenylacetylcyclopropane, also known as 1-Cyclopropyl-2-phenylethanone, is an organic compound with a unique cyclopropane ring and phenyl group. It is a versatile molecule that has been found to have various applications in different fields due to its chemical properties.

Uses

Used in Pharmaceutical Industry:
Phenylacetylcyclopropane is used as a reagent for small molecules in the pharmaceutical industry. It is particularly effective in reversing dexamethasone resistance in T-cell acute lymphoblastic leukemia (T-ALL). This application is significant because it helps overcome drug resistance, a major challenge in cancer treatment, and improves the effectiveness of existing therapies.

Upstream product

• 5500-21-0 cyclopropropanecarbonitrile 
• 6921-34-2 benzylmagnesium chloride 
• 1589-82-8 phenylmagnesium bromide 
• 143-33-9 sodium cyanide 
• 80086-21-1 5-chloro-1-phenylpentane-2-one 
• 97234-26-9 cyclopropanecarboxylic acid 2,6-di-tert-butyl-4-methylphenyl ester 
• 591-51-5 phenyllithium 
• 28488-91-7 2-cyclopropyl-1-diazo-2-ethanone 
• 71-43-2 benzene 
• 108-86-1 bromobenzene 
• 765-43-5 Cyclopropyl methyl ketone 
• 67-56-1 methanol 
• 825-76-3 α-cyclopropylstyrene 
• 23719-80-4 cyclopropylmagnesium bromide 

Downstream Products

• 56595-00-7 1-Cyclopropyl-2-phenyl-ethylamin 
• 18729-52-7 2-phenyl-1-cyclopropylethanol 
• 4266-03-9 N-Methyl-2-(phenylmethyl)pyrrolidine 
• 56595-07-4 1-Cyclopropyl-2-phenylethyl-2-cyanethyl-amin 
• 1039104-02-3 5-phenyl-2,3,6,7-tetrahydrobenzofuran-4(5H)-one 
• 1039103-85-9 7-phenyl-2,3,6,7-tetrahydrobenzofuran-4(5H)-one 
• 1071842-34-6 3-(2-chloroethyl)-5-phenyl-4H-pyran-4-one 
• 1198272-13-7 C₁₃H₁₂O₃ 
• 1198272-14-8 C₁₇H₁₆O₅ 
• 1198272-04-6 C₁₆H₁₆O₅ 
• 1190963-39-3 C₁₇H₂₈OSi 
• 1190963-40-6 (Z)-2-tert-butyldimethylsiloxy-1-phenyl-2-pentene 
• 1607817-40-2 4-cyclopropyl-5-phenylpyrimidin-2-amine 
• 84040-29-9 2-bromo-2-cyclopropyl-1-phenylethan-1-one 

Relevant articles and documents

B(C6F5)3-Catalyzed Diastereoselective Formal (4 + 1)-Cycloaddition of Vinylcyclopropanes and Et2SiH2

A formal (4 + 1)-cycloaddition of vinylcyclopropanes and Et2SiH2 to afford 3,4-disubstituted silolanes is reported. The reaction sequence commences with the known B(C6F5)3-catalyzed alkene hydrosilylation with dihydrosilanes. Cleavage of the remaining Si-H bond in the hydrosilylation product assisted by B(C6F5)3 leads to formation of a cyclopropane-stabilized silylium ion. The activated cyclopropane ring is then opened by the in situ-generated borohydride accompanied by ring closure to the silolane. The diastereoselectivity is rationalized by a mechanistic model.

B(C6F5)3-Catalyzed Hydrosilylation of Vinylcyclopropanes

A hydrosilylation of vinylcyclopropanes (VCPs) catalyzed by the strong boron Lewis acid B(C6F5)3 is reported. For the majority of VCPs, little or no ring opening of the cyclopropyl unit is observed. Conversely, for VCPs with bulky R groups, such as ortho-substituted aryl rings or branched alkyl residues, ring opening is the exclusive reaction pathway. This finding is explained by the thwarted hydride delivery to a sterically shielded, β-silicon-stabilized cyclopropylcarbinyl cation intermediate.

RhI-catalyzed benzo/[7+1] cycloaddition of cyclopropyl-benzocyclobutenes and CO by merging thermal and metal-catalyzed C-C bond cleavages

A Rh-catalyzed benzo/[7+1] cycloaddition of cyclopropyl-benzocyclobutenes (CP-BCBs) and CO to benzocyclooctenones has been developed. In this reaction, CP-BCB acts as a benzo/7-C synthon and the reaction involves two C-C bond cleavages: a thermal electrocyclic ring-opening of the four-membered ring in CP-BCB and a Rh-catalyzed C-C cleavage of the cyclopropane ring.