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

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

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 
• 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 
• 142627-18-7 1-cyclopropyl-1,2-diphenylethanol 

Relevant articles and documents

Light-Driven Carbene Catalysis for the Synthesis of Aliphatic and α-Amino Ketones

Single-electron N-heterocyclic carbene (NHC) catalysis has gained attention recently for the synthesis of C?C bonds. Guided by density functional theory and mechanistic analyses, we report the light-driven synthesis of aliphatic and α-amino ketones using single-electron NHC operators. Computational and experimental results reveal that the reactivity of the key radical intermediate is substrate-dependent and can be modulated through steric and electronic parameters of the NHC. Catalyst potential is harnessed in the visible-light driven generation of an acyl azolium radical species that undergoes selective coupling with various radical partners to afford diverse ketone products. This methodology is showcased in the direct late-stage functionalization of amino acids and pharmaceutical compounds, highlighting the utility of single-electron NHC operators.

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.

Alternative approach toward the generation of benzylic zinc reagent: Direct oxidative addition of active zinc into the carbon-oxygen bond of benzyl mesylates

The use of highly active zinc, prepared by the Rieke method, for the direct preparation of benzylic zinc mesylate was investigated. The oxidative addition of highly active zinc to benzyl mesylate was easily completed under mild conditions. The resulting benzylic zinc mesylates were employed in subsequent cross-coupling reactions with a broad range of electrophiles, and the formation of the corresponding products was successful.

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.

Small molecule that reverses dexamethasone resistance in t-cell acute lymphoblastic leukemia (T-ALL)

Glucocorticoids are one of the most utilized and effective therapies in treating T-cell acute lymphoblastic leukemia. However, patients often develop resistance to glucocorticoids, rendering these therapies ineffective. We screened 9517 compounds, selected for their lead-like properties, chosen from among 3372615 compounds, against a dexamethasone-resistant T-ALL cell line to identify small molecules that reverse glucocorticoid resistance. We synthesized analogues of the most effective compound, termed J9, from the screen in order to define the scaffolds structure-activity relationship. Active compounds restored sensitivity to glucocorticoids through upregulation of the glucocorticoid receptor. This compound and mechanism may provide a strategy for overcoming glucocorticoid resistance in patients with T-ALL.

Oxidative rearrangements of arylalkenes with [hydroxy(tosyloxy)iodo]benzene in 95% methanol: A general, regiospecific synthesis of α-aryl ketones

The treatment of arylalkenes with [hydroxy(tosyloxy)iodo]benzene in 95% methanol affords the corresponding α-aryl ketones. This oxidative rearrangement is general for acyclic and cyclic arylalkenes and permits regioselective syntheses of isomeric α-phenyl ketone pairs.

Synthesis of Nitriles from Haloesters, Haloketones and Haloethers

The action of NaCN on haloesters, haloketones and haloethers has been studied.Haloesters wherein halogen and ester functions are located on adjacent carbon atoms, do not furnish the corresponding nitriles, whereas those with halogen and ester functions not located on adjacent carbon atoms, furnish the corresponding nitriles in good yields.The presence of hydroxy or ether function on the carbon adjacent to primary halide bearing carbon atom does not interfere in the reaction with cyanide. δ-Haloketones are transformed to ketonitriles, γ-Haloketones are transformed to cyclopropyl ketones and epoxyhalides to epoxynitriles.

Alkylation of Benzene with α-Diazoketones via Cycloheptatrienyl Intermediates

Benzyl ketones can be synthesised efficiently from benzene and α-diazoketones with sequential catalysis by rhodium(II) trifluoroacetate and trifluoroacetic acid; the process involves cycloheptatrienyl intermediates.

Synthesis of Some Substituted Pyrrolidines from Cyclopropyl Carbonyl Compounds

A series of alkyl and aryl cyclopropyl carbonyl compounds, when refluxed in N-methylformamide in the presence of magnesium chloride, gave variously substituted pyrrolidines.