174790-32-0

Usage

Uses

Used in Organic Synthesis:
1-(4-chlorobutyl)cyclopropanol is used as a building block in organic synthesis for the creation of various chemical compounds. Its unique structure allows for the development of a wide range of products with different applications.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 1-(4-chlorobutyl)cyclopropanol is utilized as an intermediate in the production of various pharmaceuticals. Its role in the synthesis process is crucial for the development of new drugs and medications.
Used in Agrochemical Production:
Similarly, 1-(4-chlorobutyl)cyclopropanol is employed as an intermediate in the production of agrochemicals, contributing to the development of substances used in agriculture for pest control, fertilizers, and other applications.

Upstream product

• 3153-37-5 methyl 4-chlorobutyrate 
• 925-90-6 ethylmagnesium bromide 
• 4635-59-0 4-Chlorobutanoyl chloride 
• 3153-36-4 4-chloro-butyric acid ethyl ester 

Relevant academic research and scientific papers

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.).

Two-step conversion of carboxylic esters into distally fluorinated ketones: Via ring cleavage of cyclopropanol intermediates: Application of sulfinate salts as fluoroalkylating reagents

Tertiary cyclopropanols easily available from carboxylic esters have been used in the synthesis of distally fluorinated ketones. Cyclopropane ring cleavage reactions in methanol with aqueous tert-butyl hydroperoxide in the presence of a copper(ii) acetate catalyst and sodium triflinate (Langlois reagent) afford β-trifluoromethyl ketones in 16-74% isolated yields. Sodium triflinate serves as a precursor of reactive trifluoromethyl copper species, enabling ring-opening trifluoromethylation, as evidenced by mechanistic studies. We also demonstrate here that other sulfinate salts, such as sodium 1,1-difluoroethanesulfinate, sodium 2-(4-bromophenyl)-1,1-difluoroethanesulfinate and sodium 1-(trifluoromethyl)cyclopropanesulfinate, can be used as fluoroalkylation reagents, resulting in the corresponding fluorinated ketones.

Synthesis of γ-keto sulfones by copper-catalyzed oxidative sulfonylation of tertiary cyclopropanols

Tertiary cyclopropanols undergo ring-opening oxidative sulfonylation to afford γ-keto sulfones when reacting with sulfinate salts in the presence of a copper(ii) acetate catalyst and an oxidant (tert-butyl hydroperoxide or atmospheric oxygen). Various fluoroalkyl, aryl and alkyl sulfinate salts are successfully employed as sulfonylation reagents, affording the corresponding sulfones in up to 94% yields. The experimental protocol is mild and tolerates a number of functionalities in the cyclopropanol substrate. The reaction proceeds via a one-pot oxidation-Michael addition mechanism and can serve as a useful addition to the existing methods for the preparation of γ-keto sulfones based on the sulfa-Michael reaction.

ARYL, HETEROARYL, AND HETEROCYCLIC COMPOUNDS FOR TREATMENT OF MEDICAL DISORDERS

Compounds, methods of use, and processes for making inhibitors of complement Factor D comprising Formula I, or a pharmaceutically acceptable salt or composition thereof wherein R12 or R13 on the A group is an aryl, heteroaryl or heterocycle (R32) are provided. The inhibitors of Factor D described herein reduce the excessive activation of complement.

Simple access to β-trifluoromethyl-substituted ketones via copper-catalyzed ring-opening trifluoromethylation of substituted cyclopropanols

Tertiary cyclopropanols react rapidly with Togni reagent in methanol at room temperature in the presence of catalytic amounts (3 mol%) of CuCl affording β-trifluoromethyl ketones in 65-73% isolated yields. Ring opening in 1,2-dialkylsubstituted cyclopropanols gives a mixture of isomeric β-trifluoromethyl ketones in about 50% combined yield.

Dihydropyrrolo[1,2-b]pyrazoles: Withasomnine and related compounds

In the paper we indicate the increasing importance of derivatives containing a dihydropyrrolo[1,2-b]pyrazole (DPP) core. We try to show our synthetic approach based on an improved Kulinkovich method as well as our new synthetic pathway. A complex methodology involving the preparation of substituted DPPs focuses on withasomnine and the synthesis of several structurally related compounds. The developed reaction protocols enable the preparation of the mentioned bicyclic system with broadly diverse substitution. Thus, we are able to prepare systems with aliphatic, aromatic, polyaromatic, heteroaromatic, TMS, and even adamantane substitution with known biologically active properties. The reaction protocol, consisting of two multi-step synthetic pathways, includes Sonogashira and Suzuki-Miyaura cross-coupling reactions, allenyl synthon formation, Kulinkovich cyclopropanation, ring transformations, and nonsymmetrical homoallenyl azines cycloadditions. Moreover, we prepared compounds with a resemblance to other bioactive species: fadrozole, nagstatine, an antitumor agent LY2109761 and a mixed lineage kinase 7 inhibitor DHP-2.

PYRAZOLYL DERIVATIVES AS SYK INHIBITORS

The present invention provides novel pyrazole derivatives of formula I which are potent inhibitors of spleen tyrosine kinase, and are useful in the treatment and prevention of diseases mediated by said enzyme, such as asthma, COPD, rheumatoid arthritis, and cancer.

2-PYRIDYL CARBOXAMIDE-CONTAINING SPLEEN TYROSINE KINASE (SYK) INHIBITORS

The invention provides certain 2-pyridyl carboxamide-containing compounds of the Formula (I) or pharmaceutically acceptable salts thereof, wherein A and B are as defined herein. The invention also provides pharmaceutical compositions comprising such compounds, and methods of using the compounds for treating diseases or conditions mediated by Spleen Tyrosine Kinase (Syk) kinase.

New synthetic route to the alkaloid withasomnine by ring transformation of a functionalized cyclopropanol via the parent pyrrolo[1,2-b]pyrazole

Withasomnine has been prepared by rearrangement of 1-(3-chloropropyl)-cyclopropanol into 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole, followed by bromination and [NiCl2(dppp)]-catalyzed phenylation.