23595-96-2

Usage

Uses

Used in Organic Synthesis:
Bicyclo[3.1.0]hexane, 6,6-dichlorois used as a building block in organic synthesis for the creation of more complex molecules. Its unique structure and reactivity allow for the formation of various derivatives, which can be further utilized in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Research:
In pharmaceutical research, Bicyclo[3.1.0]hexane, 6,6-dichloroserves as a key intermediate for the development of novel drug candidates. Its unique structural features and reactivity enable the design and synthesis of new bioactive compounds with potential therapeutic applications.
Used in New Materials Development:
Bicyclo[3.1.0]hexane, 6,6-dichlorohas been studied for its potential applications in the development of new materials. Its rigid and stable structure, along with its reactivity, makes it a promising candidate for the creation of advanced materials with specific properties, such as high thermal stability, mechanical strength, or unique optical characteristics.
Used as a Chiral Ligand in Asymmetric Catalysis:
In asymmetric catalysis, Bicyclo[3.1.0]hexane, 6,6-dichlorois used as a chiral ligand to facilitate the synthesis of enantiomerically pure compounds. Its unique structure provides a distinct environment for the catalysis process, enabling the selective formation of desired enantiomers with high yields and selectivity. This application is particularly relevant in the synthesis of chiral pharmaceuticals and agrochemicals, where enantioselectivity is crucial for biological activity and safety.

InChI:InChI=1/C6H8Cl2/c7-6(8)4-2-1-3-5(4)6/h4-5H,1-3H2

Upstream product

• 56-23-5 tetrachloromethane 
• 142-29-0 cyclopentene 
• 848768-04-7 3-chloro-3-(p-nitrophenoxy)diazirine 
• 67-66-3 chloroform 

Downstream Products

• 119-42-6 2-cyclohexylphenol 
• 13283-35-7 p-(2-Chlorcyclohex-2-en-1-yl)-phenol 
• 13283-40-4 o-(2-Chlor-cyclohex-2-en-1-yl)-phenol 
• 1131-60-8 p-cyclohexylphenol 
• 40099-06-7 1,6-dichlorocyclohexene 
• 933-02-8 1-cyclopentylidenepropan-2-one 
• 79054-41-4 1,6-Bis-methoxymethyl-cyclohexene 
• 79054-40-3 (6-Methoxymethyl-cyclohex-1-enyl)-trimethyl-silane 
• 1333495-30-9 3-chloro-5,6-dihydro-4H-cyclopenta[c]isoxazole 
• 23231-18-7 2-dichloromethylidenecyclopentanone oxime 
• 111581-86-3 2-chlorocyclohex-2-enamine 
• 116330-66-6 2-(2-chlorocyclohex-2-en-1-yl)isoindoline-1,3-dione 
• 142160-60-9 C₂₆H₂₁ClO 
• 1159-86-0 o-dibenzoylbenzene 

Relevant academic research and scientific papers

Dichlorodiazirine: A nitrogenous precursor for dichlorocarbene

The reaction of 3-p-nitrophenoxy-3-chlorodiazirine with a 1.1:1.0:1.6 blend of tetrabutylammonium chloride, cesium chloride, and the ionic liquid 1-butyl-3-methylimidazolium chloride at 40-50 °C under vacuum at 1 mm·Hg produced a melt from which dichlorod

Discovery of Novel 1-Cyclopentenyl-3-phenylureas as Selective, Brain Penetrant, and Orally Bioavailable CXCR2 Antagonists

CXCR2 has emerged as a therapeutic target for not only peripheral inflammatory diseases but also neurological abnormalities in the central nervous system (CNS). Herein, we describe the discovery of a novel 1-cyclopentenyl-3-phenylurea series as potent and CNS penetrant CXCR2 antagonists. Extensive SAR studies, wherein molecules' property forecast index (PFI) was carefully optimized for overall balanced developability profiles, led to the discovery of the advanced lead compound 68 with a desirable PFI. Compound 68 demonstrated good in vitro pharmacology with excellent selectivity over CXCR1 and other chemokine receptors. Rat and dog pharmacokinetics (PK) revealed good oral bioavailability, high oral exposure, and desirable elimination half-life of the compound in both species. In addition, the compound demonstrated dose-dependent efficacy in the in vivo pharmacology neutrophil infiltration "air pouch" model in rodents after oral administration. Further, compound 68 is a CNS penetrant molecule with high unbound fraction in brain tissue.

Novel ambiphilic dichlorocarbenoid equivalent in alkene cyclopropanation and carbonyl olefination

The Ti-Mg-dichloromethylene complexes derived from the oxidative addition of CCl4 to the Mg-TiCl4 bimetallic species serve as a novel class of ambiphilic dichlorocarbenoid equivalents. Not only is Ti-Mg-dichlorocarbenoid highly selective but also it seems highly reactive in both alkene cyclopropanations and carbonyl dichloromethylenations.

Synthesis, characterization, and utility of trialkyl(3-sulfopropyl)ammonium betaines as new phase transfer reagents

Synthesis of water-soluble phase transfer reagents, trialkyl(3-sulfopropyl)ammonium betaines and its utility in various hydroxide-ion initiated reactions are described.

A new phase transfer reagent for the addition of dichlorocarbene to olefins under mild PTC conditions

A three-step synthetic route to a novel water soluble phase transfer reagent, Diquat (Dq-Br), viz., 2-benzilidine-N,N,N,N',N',N'- hexaethyl propane-1,3 diammonium dibromide and its utility in various dichlorocarbenations to olefins are described.

Carbon Tetrachloride-Dimethyl Sulphone-Potassium Hydroxide-t-Butyl Alcohol: a Convenient New Reagent for gem-Dichloromethylenation of Alkenes

The action of dimethyl sulphone-potassium hydroxide-t-butyl alcohol on carbon tetrachloride readily affords dichlorocarbene.In the presence of alkenes, gem-dichlorocyclopropanes are formed in moderate to high yields.The dichlorocarbene generated by this procedure adds stereospecifically to alkenes with retention of geometric configuration about the carbon-carbon double bond.Relative reactivities of alkenes towards the CCl4-derived dichlorocarbene parallel the nucleophilicities of the alkenes and indicate that free dichlorocarbene is probably involved.

BICYCLOALKYLSILANES: NOUVELLE SYNTHESE ET REACTIVITE

A new and competitive synthesis of bicyclotrimethylsilanes is reported, involving a facile and rapid process, and giving both endo and exo isomers.The behaviour of these species towrads acids (HCl, (AcOH)2BF3) has ben investigated.The stereochemist

RELATIVE REACTIVITY OF CYCLOOLEFINS TOWARD DICHLOROCARBENES

The relative rate constants for the addition of dichloro- and dibromocarbenes to cis- and trans-cycloalkenes, containing up to 12 carbon atoms in the ring, were determined.It was shown that the reaction is kinetically controlled and that the conformation of the ring exerts an important effect on the rate.

GEM-DISILYLCYCLOPROPANES: PREPARATION ET UTILISATION EN SYNTHESE ORGANIQUE

A simple general route for the conversion of olefins to gem-disilylcyclopropanes, involving the dichlorocyclopropanation of the double bond followed by silylation using the Me3SiCl/Li/THF reagent at 0-10 deg C, is described.Acetylation of bicyclic derivatives thus obtained constitutes an original synthesis of cycloalkylidene ketones by a process more convenient than those previously used, and also provides new acetyl dihydrofurans.