109240-30-4

Usage

Uses

Used in Pharmaceutical Synthesis:
1-(4-bromophenyl)cyclopropanol is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used as a Building Block in Organic Chemistry:
1-(4-broMophenyl)cyclopropanol serves as a valuable building block in organic chemistry, enabling the creation of a wide range of organic molecules with diverse functionalities.
Used in Asymmetric Catalysis:
1-(4-bromophenyl)cyclopropanol is recognized for its potential use as a ligand in asymmetric catalysis. Its chiral properties make it a promising candidate for enhancing the selectivity and efficiency of catalytic reactions, leading to the production of enantiomerically pure compounds.
Used as a Chiral Auxiliary in Organic Synthesis:
In organic synthesis, 1-(4-bromophenyl)cyclopropanol is utilized as a chiral auxiliary. Its ability to induce chirality in target molecules is crucial for the synthesis of biologically active compounds with specific stereochemistry, which is essential for their biological activity and selectivity.

Upstream product

• 186581-53-3 diazomethane 
• 55991-66-7 1-(4-bromophenyl)-1-(trimethylsilyloxy)ethylene 
• 5798-75-4 Ethyl 4-bromobenzoate 
• 925-90-6 ethylmagnesium bromide 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 2386-64-3 ethylmagnesium chloride 
• 99-90-1 para-bromoacetophenone 
• 75-11-6 diiodomethane 
• 75-09-2 dichloromethane 
• 99-73-0 para-bromophenacyl bromide 

Downstream Products

• 1217864-25-9 [1-(4-bromophenyl)cyclopropoxy](tert-butyl)dimethylsilane 
• 31736-73-9 4-bromophenyl 2-chloroethyl ketone 
• 13552-48-2 1-(4-bromo-phenyl)-3-morpholin-4-yl-propan-1-one 
• 1488363-78-5 (S)-3-{4-[1-(4'-tert-butyl-2,6-dimethylbiphenyl-4-yloxy)-4,4,4-trifluorobutyl]benzamido}propanoic acid 

Relevant academic research and scientific papers

Copper-Catalyzed Cyclopropanol Ring Opening Csp3-Csp3 Cross-Couplings with (Fluoro)Alkyl Halides

Novel and general copper-catalyzed cyclopropanol ring opening cross-coupling reactions with difluoroalkyl bromides, perfluoroalkyl iodides, monofluoroalkyl bromides, and 2-bromo-2-alkylesters to synthesize various β-(fluoro)alkylated ketones are reported.

The reagent Et2AlX/CH2N2 in cyclopropanation of sterically hindered olefins, as well as oxygen- and nitrogen-containing unsaturated compounds

A transition-metal-free method of cyclopropanation of sterically hindered olefins, substituted allylic alcohols, allylamines, and vinyl silyl ethers was developed using diazomethane in the presence of organic aluminum halides.

Synthesis of γ-Keto Sulfones through a Three-Component Reaction of Cyclopropanols, DABCO ? (SO2)2 and Alkyl Halides

A route to γ-keto sulfones through a metal-free reaction of cyclopropanols, DABCO ? (SO2)2 and alkyl halides is described. This reaction occurs under mild conditions in the absence of any catalysts, additives, or oxidants. Various functional groups including as ester, amino, methoxy, bromo, trifluoromethyl, nitro and carbonyl are tolerated well in this transformation, and the corresponding γ-keto sulfones are afforded in 35% to 95% yields. The proposed mechanism implies that this reaction proceeds through γ-keto sulfinate intermediate generated in situ, which further undergoes nucleophilic substitution with alkyl halides leading to γ-keto sulfones. (Figure presented.).

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.

MUSCARINIC ACETYLCHOLINE M1 RECEPTOR ANTAGONISTS

Provided herein, inter alia, are compounds which are useful as antagonists of the muscarinic acetylcholine receptor M1 (mAChR M1); synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of treating neurological and psychiatric disorders associated with muscarinic acetylcholine receptor dysfunction using the compounds and compositions.

Iron-Catalyzed Ring-Opening Reactions of Cyclopropanols with Alkenes and TBHP: Synthesis of 5-Oxo Peroxides

The ring opening of cyclopropanols is rarely used in multicomponent reactions. Herein we report the three-component reaction of cyclopropanols with alkenes and tert-butyl hydroperoxide (TBHP) catalyzed by an iron catalyst. This protocol enables the incorporation of both the β-carbonyl fragment and a peroxy unit across the C=C double bond regioselectively, thus allowing an efficient, facile access to 5-oxo peroxides. Modification of the biologically active molecules and various downstream derivatizations of the peroxides are also demonstrated.

Copper-mediated tandem ring-opening/cyclization reactions of cyclopropanols with aryldiazonium salts: Synthesis of: N -arylpyrazoles

A general method for the synthesis of structurally diverse N-arylpyrazoles from readily available cyclopropanols and aryldiazonium salts is disclosed. The reaction was conducted at room temperature within minutes with a broad substrate scope and excellent regioselectivity.

Metal-Free Direct C–H β-Carbonyl Alkylation of Heteroarenes with Cyclopropanols Mediated by K2S2O8

Direct C–H β-carbonyl alkylation of heteroarenes under metal-, acid- and photo-catalyst free conditions has been achieved. A wide scope of substrates, such as various substituted quinolines and isoquinolines, pyridines, pyridazine, benzo[d]thiazole and phenanthroline, underwent the β-carbonyl alkylation efficiently via K2S2O8-mediated ring-opening of cyclopropanols. The corresponding β-heteroarylated ketones were obtained in moderate to excellent yields and gram-scale experiments further demonstrated the practicality of this synthetic protocol. The readily available reagents, mild and environmentally benign conditions make the method extremely attractive. The reaction mechanism is also proposed.

Aryl Pyrazoles from Photocatalytic Cycloadditions of Arenediazonium

A photocatalytic synthesis of 1,5-diaryl pyrazoles from arenediazoniums and arylcyclopropanols is reported. The reaction proceeded under mild conditions (rt, 20 min) with catalytic [Ru(bpy)3]2+ under blue-light irradiation and exhibited compatibility with several functional groups (e.g., I, SF5, SO2NH2, N3, CN) and perfect levels of regiocontrol. Mechanistic studies (luminescence spectroscopy, CV, DFT, radical trapping, quantum yield determination) documented an initial oxidative quenching of the excited photocatalyst and the operation of a radical-chain mechanism.

Visible-Light-Induced Alkoxyl Radical Generation Enables Selective C(sp3)-C(sp3) Bond Cleavage and Functionalizations

The alkoxyl radical is an important reactive intermediate in mechanistic studies and organic synthesis; however, its current generation from alcohol oxidation heavily relies on transition metal activation under strong oxidative conditions. Here we report the first visible-light-induced alcohol oxidation to generate alkoxyl radicals by cyclic iodine(III) reagent catalysis under mild reaction conditions. The β-fragmentation of alkoxyl radicals enables selective C(sp3)-C(sp3) bond cleavage and alkynylation/alkenylation reactions with various strained cycloalkanols, and for the first time with linear alcohols.