32523-76-5

Upstream product

• 100-42-5 styrene 
• 3234-51-3 1,1-dibromo-2-phenylcyclopropane 
• 110889-04-8 (3-bromo-3,3-difluoroprop-1-yn-1-yl)triethylsilane 
• 104465-98-7 (3-bromoprop-1-yn-1-yl)triisopropylsilane 
• 939-89-9 (1S*,2R*)-2-phenylcyclopropane-1-carboxylic acid 
• 124-41-4 sodium methylate 
• 22985-29-1 1-bromo-1-chloro-2-phenylcyclopropane 

Downstream Products

• 86256-88-4 3-bromo-4,5-dihydro-5-phenyl-isoxazole 
• 90712-70-2 4-bromo-5-phenylisoxazoline 
• 1145-91-1 cis-(2-phenylcyclopropyl)(phenyl)methanone 
• 137601-77-5 p-(cis-2-Bromocyclopropyl)-α-methylbenzyl Chloride 
• 137601-86-6 p-(cis-2-Bromocyclopropyl)-α-methylbenzyl Alcohol 
• 78072-88-5 1-((1S,2S)-2-Bromo-cyclopropyl)-4-(1-chloro-1-methyl-ethyl)-benzene 
• 78072-82-9 1-((1S,2S)-2-Bromo-cyclopropyl)-4-isopropenyl-benzene 

Relevant academic research and scientific papers

Stereoselective Functionalization of Racemic Cyclopropylzinc Reagents via Enantiodivergent Relay Coupling

Efficient construction of optically pure molecules from readily available starting materials in a simple manner is an ongoing goal in asymmetric synthesis. As a straightforward route, transition-metal-catalyzed enantioconvergent coupling between widely available secondary alkyl electrophiles and organometallic nucleophiles has emerged as a powerful strategy to construct chiral center(s). However, the scope of racemic secondary alkylmetallic nucleophiles for this coupling remains limited in specific substrates because of the difficulties in stereoselective formation of the key alkylmetal intermediates. Here, we report an enantiodivergent strategy to efficiently achieve an array of synthetically useful chiral cyclopropanes, including chiral fluoroalkylated cyclopropanes and enantiomerically enriched cyclopropanes with chiral side chains, from racemic cyclopropylzinc reagents. This strategy relies on a one-pot, two-step enantiodivergent relay coupling process of the racemic cis-cyclopropylzinc reagents with two different electrophiles, which involves kinetic resolution of racemic cis-cyclopropylzinc reagents through a nickel-catalyzed enantioselective coupling with alkyl electrophiles, followed by a stereospecific relay coupling of the remaining enantiomeric cyclopropylzinc reagent with various electrophiles, to produce two types of functionalized chiral cyclopropanes with opposite configurations on the cyclopropane ring. These chiral cyclopropanes are versatile synthons for diverse transformations, rendering this strategy effective for obtaining structurally diversified molecules of medicinal interest.

Structure activity relationship and modeling studies of inhibitors of lysine specific demethylase 1

Post-translational modifications of histone play important roles in gene transcription. Aberrant methylation of histone lysine sidechains have been often found in cancer. Lysine specific demethylase 1 (LSD1), which can demethylate histone H3 lysine 4 (H3K4) and other proteins, has recently been found to be a drug target for acute myeloid leukemia. To understand structure activity/selectivity relationships of LSD1 inhibitors, several series of cyclopropylamine and related compounds were synthesized and tested for their activities against LSD1 and related monoamine oxidase (MAO) A and B. Several cyclopropylamine containing compounds were found to be highly potent and selective inhibitors of LSD1. A novel series cyclopropylimine compounds also exhibited strong inhibitory activity against LSD1.Structure activity relationships (SAR) of these compounds are discussed. Docking studies were performed to provide possible binding models of a representative compound in LSD1 and MAO-A. Moreover, these modeling studies can rationalize the observed SARs and selectivity.

A Convenient Stereoselective Reduction of Gem-Dibromides with a Combination of Dimethyl Phosphite and Potassium Carbonate

An efficient and highly stereoselective reduction of a gem-dibromocyclopropane to the corresponding monobromocyclopropane under mild reaction conditions was developed using a combination of dimethyl phosphite and potassium carbonate. This reaction provided a simple and practical way for the synthesis of the valuable monobromocyclopropanes and β-monobromoalkenes.

A Novel Cathode Material for Cathodic Dehalogenation of 1,1-Dibromo Cyclopropane Derivatives

Leaded bronze turned out to be an excellent cathode material for the dehalogenation reaction of cyclopropanes without affecting the strained molecular entity. With this particular alloy, beneficial properties of lead cathodes are conserved, whereas the corrosion of cathode is efficiently suppressed. The solvent in the electrolyte determines whether a complete debromination reaction is achieved or if the process can be selectively stopped at the monobromo cyclopropane intermediate. The electroorganic conversion tolerates a variety of functional groups and can be conducted at rather complex substrates like cyclosporine A. This approach allows the sustainable preparation of cyclopropane derivatives.

Synthesis of the racemic forms of carbon-carbon double bond locked analogues of strobilurins which are characterized by a 2-arylcyclopropane ring cis-substituted at C-1 by the methyl (E)-3-methoxypropenoate unit

The racemic forms of three new carbon-carbon double bond locked analogues of strobilurins, which are characterized by a 2-arylcyclopropane ring cis-substituted at C-1 by the methyl (E)-3-methoxypropenoate unit, have been synthesized according to a strateg

Hydrodehalogenation of 1,1-dibromocyclopropanes by Grignard reagents promoted by titanium compounds

1,1-Dibromocyclopropanes are converted into the corresponding monobromocyclopropanes (as mixtures of stereoisomers where appropriate) by reaction with 1.0-1.3 mol equiv. of ethylmagnesium bromide and 2-10 mol% titanium isopropoxide for 90%). With ethylmagnesium bromide, the reaction occurs very slowly in the absence of catalyst; with methylmagnesium bromide, the reaction does occur in the absence of catalyst, but is only slightly promoted in the presence of titanium isopropoxide. Reactions with a number of other Grignard reagents are also discussed. In the case of phenethylmagnesium bromide, the major product containing the phenethyl-group is ethylbenzene, together with small amounts of styrene and ethyl 4-phenyl-2-butyl ether, a product of trapping of the solvent, ether. In other cases, relatively large amounts of a diether, formally derived by hydrogen ion adjacent to the ether oxygen followed by dimerisation, are isolated. No products were identified incorporating the cyclopropane and either the Grignard alkyl group or the solvent. Labelling studies indicate that the hydrogen introduced into the cyclopropane is not derived from either the α- or β-positions of the Grignard reagent. When the reduction is carried out with phenethylmagnesium bromide in d8-tetrahydrofuran both monobromides contain deuterium.

Reduction of geminal dihalocyclopropanes with ethylmagnesium bromide in the presence of tetraisopropoxytitanium

Reactions of geminal dichloro(dibromo)cyclopropanes with excess ethylmagnesium bromide in the presence of tetraisopropoxytitanium as catalyst lead to the corresponding stereoisomeric monohalocyclopropanes in good yields. A mechanism is proposed which invo

Preparation and Spectroscopic Analysis of 1-Aryl-2-bromocyclopropanes

1-Aryl-2-bromocyclopropanes have been prepared in good yields by reduction of 1-aryl-2,2-dibromocyclopropanes with diethyl phosphite and triethylamine.Characteristic stretching lines occur at about 1260 and 555 +/- 15 cm-1 for the cis isomers a

A simple and efficient hydrodehalogenation of 1,1-dihalocyclopropanes

1,1-Dibromo- and 1,1-dichlorocyclopropanes are converted into the corresponding monohalocyclopropanes (as mixtures of stereoisomers where appropriate) by reaction with 1.2-1.3 mol. equiv. of ethyl magnesium bromide and a small amount of titanium isopropoxide in ether. In the presence of an excess of ethylmagnesium bromide the product from the dibromide is the non- halogenated cyclopropane. Copyright (C) 1996 Elsevier Science Ltd.