25253-51-4

Usage

Uses

Used in Organic Synthesis:
8-(4-CHLOROPHENYL)-1,4-DIOXASPRIRO[4,5]DECANE is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows for a wide range of chemical reactions, making it a valuable building block for the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 8-(4-CHLOROPHENYL)-1,4-DIOXASPRIRO[4,5]DECANE is used as a starting material for the synthesis of various drug candidates. Its chemical properties and reactivity make it suitable for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
8-(4-CHLOROPHENYL)-1,4-DIOXASPRIRO[4,5]DECANE is also used in the agrochemical industry as a precursor for the synthesis of various agrochemicals, such as insecticides, herbicides, and fungicides. Its unique structure and reactivity contribute to the development of new and effective agrochemical products.
Used in Specialty Chemicals:
In the specialty chemicals industry, 8-(4-CHLOROPHENYL)-1,4-DIOXASPRIRO[4,5]DECANE is used as a building block for the synthesis of various specialty chemicals, such as dyes, pigments, and fragrances. Its versatility in chemical reactions allows for the creation of new and innovative products with unique properties and applications.

InChI:InChI=1/C14H17ClO2/c15-13-3-1-11(2-4-13)12-5-7-14(8-6-12)16-9-10-17-14/h1-4,12H,5-10H2

Upstream product

• 106-39-8 bromochlorobenzene 
• 637-87-6 1-Chloro-4-iodobenzene 
• 4746-97-8 cyclohexanedione monoethylene ketal 
• 126991-59-1 8-(4-chlorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol 
• 126991-60-4 4-(4-chlorophenyl)cyclohex-3-enone monoehtylene ketal 

Downstream Products

• 14472-80-1 4-(4-chlorophenyl)cyclohexan-1-one 
• 1421369-93-8 4-(4-chlorophenyl)-1-(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)cyclohexyl 2,2,2-trifluoroacetate 
• 1409956-67-7 cis/trans-2-(4-(4-chlorophenyl)cyclohexyl)-3,4-dihydronaphthalen-1(2H)-one 
• 1409956-62-2 2-(4-(4-chlorophenyl)cyclohex-1-en-1-yl)-3,4-dihydronaphthalen-1(2H)-one 
• 1203609-10-2 cis-2-[4-(4-chlorophenyl)cyclohexyl]-1,4-naphthoquinone 
• 1409957-04-5 trans-2-(4-(4-chlorophenyl)cyclohexyl)naphthalen-1-ol 
• 1409957-10-3 cis-2-(4-(4-chlorophenyl)cyclohexyl)naphthalen-1-ol 
• 1409956-99-5 cis/trans-2-(4-(4-chlorophenyl)cyclohexyl)naphthalen-1-ol 
• 1409956-88-2 trans-2-bromo-2-(4-(4-chlorophenyl)cyclohexyl)-3,4-dihydronaphthalen-1(2H)-one 
• 1409956-94-0 cis-2-bromo-2-(4-(4-chlorophenyl)cyclohexyl)-3,4-dihydronaphthalen-1(2H)-one 
• 1409956-84-8 cis/trans-2-bromo-2-(4-(4-chlorophenyl)cyclohexyl)-3,4-dihydronaphthalen-1(2H)-one 
• 1409956-73-5 trans-2-(4-(4-chlorophenyl)cyclohexyl)-3,4-dihydronaphthalen-1(2H)-one 
• 1409956-79-1 cis-2-(4-(4-chlorophenyl)cyclohexyl)-3,4-dihydronaphthalen-1(2H)-one 
• 1203609-11-3 cis/trans-(4-(4-chlorophenyl)cyclohexyl)naphthalen-1,4-dione 

Relevant academic research and scientific papers

The Silicon-Hydrogen Exchange Reaction: A Catalytic σ-Bond Metathesis Approach to the Enantioselective Synthesis of Enol Silanes

The use of chiral enol silanes in fundamental transformations such as Mukaiyama aldol, Michael, and Mannich reactions as well as Saegusa-Ito dehydrogenations has enabled the chemical synthesis of enantiopure natural products and valuable pharmaceuticals. However, accessing these intermediates in high enantiopurity has generally required the use of either stoichiometric chiral precursors or stoichiometric chiral reagents. We now describe a catalytic approach in which strongly acidic and confined imidodiphosphorimidates (IDPi) catalyze highly enantioselective interconversions of ketones and enol silanes. These "silicon-hydrogen exchange reactions"enable access to enantiopure enol silanes via tautomerizing σ-bond metatheses, either in a deprotosilylative desymmetrization of ketones with allyl silanes as the silicon source or in a protodesilylative kinetic resolution of racemic enol silanes with a carboxylic acid as the silyl acceptor.

Enantioselective Synthesis of Chiral Oxime Ethers: Desymmetrization and Dynamic Kinetic Resolution of Substituted Cyclohexanones

Axially chiral cyclohexylidene oxime ethers exhibit unique chirality because of the restricted rotation of C=N. The first catalytic enantioselective synthesis of novel axially chiral cyclohexylidene oximes has been developed by catalytic desymmetrization of 4-substituted cyclohexanones with O-arylhydroxylamines and is catalyzed by a chiral BINOL-derived strontium phosphate with excellent yields and good enantioselectivities. In addition, chiral BINOL-derived phosphoric acid catalyzed dynamic kinetic resolution of α-substituted cyclohexanones has been performed and yields versatile intermediates in high yields and enantioselectivities.

A Versatile Route to Unstable Diazo Compounds via Oxadiazolines and their Use in Aryl–Alkyl Cross-Coupling Reactions

Coupling of readily available boronic acids and diazo compounds has emerged recently as a powerful metal-free carbon–carbon bond forming method. However, the difficulty in forming the unstable diazo compound partner in a mild fashion has hitherto limited their general use and the scope of the transformation. Here, we report the application of oxadiazolines as precursors for the generation of an unstable family of diazo compounds using flow UV photolysis and their first use in divergent protodeboronative and oxidative C(sp2)?C(sp3) cross-coupling processes, with excellent functional-group tolerance.

Optimization of TRPV6 calcium channel inhibitors using a 3D ligand-based virtual screening method

Herein, we report the discovery of the first potent and selective inhibitor of TRPV6, a calcium channel overexpressed in breast and prostate cancer, and its use to test the effect of blocking TRPV6-mediated Ca2+-influx on cell growth. The inhib

A novel process for synthesis of atovaquone

A stereospecific efficient process for synthesis of atovaquone i.e. trans-2-[4-(4-chlorophenyl)cyclohexyl ]-3-hydroxy-1,4-naphthalenedione and its cis isomer from commercially available raw materials such as α-tetralone and 4-(4-chlorophenyl)cyclohexanone

Enantioselective baeyer-villiger oxidation: Desymmetrization of meso cyclic ketones and kinetic resolution of racemic 2-arylcyclohexanones

Catalytic enantioselective Baeyer-Villiger (BV) oxidations of racemic and meso cyclic ketones were achieved in the presence of chiral N,N'-dioxide-Sc III complex catalysts. The BV oxidations of prochiral cyclohexanones and cyclobutanones afforded series of optically active μ- and γ-lactones, respectively, in up to 99% yield and 95% ee. Meanwhile, the kinetic resolution of racemic 2-arylcyclohexanones was also realized via an abnormal BV oxidation. Enantioenriched 3-aryloxepan-2-ones, whose formation is counter to the migratory aptitude, were obtained preferentially. Both the lactones and the unreacted ketones were obtained with high ee values.

Enantioselective baeyer-villiger oxidation: Desymmetrization of meso cyclic ketones and kinetic resolution of racemic 2-arylcyclohexanones

Catalytic enantioselective Baeyer-Villiger (BV) oxidations of racemic and meso cyclic ketones were achieved in the presence of chiral N,N'-dioxide-Sc III complex catalysts. The BV oxidations of prochiral cyclohexanones and cyclobutanones afforded series of optically active μ- and γ-lactones, respectively, in up to 99% yield and 95% ee. Meanwhile, the kinetic resolution of racemic 2-arylcyclohexanones was also realized via an abnormal BV oxidation. Enantioenriched 3-aryloxepan-2-ones, whose formation is counter to the migratory aptitude, were obtained preferentially. Both the lactones and the unreacted ketones were obtained with high ee values.

NOVEL METHOD FOR PREPARATION OF ATOVAQUONE

Provided is a process of preparation of 2-[trans,-4-(4'-chlorophenyl)cyclohexyl]-3-hydroxy- 1,4-naphthoquinone, i.e. Atovaquone [I] which is cost effective, green, and eco-friendly process, without separation of any diastereomers or geometric isomers of intermediates obtained during the reactions. Also provided is separation of 'cis' and 'trans ' isomer of intermediates VI, VII and VIII through selective crystallization in an appropriate solvent. A method for converting 2-[cis,-4-(4'-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone to 2-[trans-4-(4'-chlorophenyl)cyclohexyl]-3-hydroxy-l,4-naphthoquinone in presence of Lewis/ Bronsted acid is also provided. A process for preparation of compound 2-(4-(4- chlorophenyl)- 1 -hydroxy cyclohexyl)-3,4-dihydronaphthalen- 1 (2H)-one [IV] comprising condensation of (1,2-dihydronaphthalen-4-yloxy)trimethylsilane [II] with 4-(4- chlorophenyl)cyclohexanone [III] in presence of Lewis acid in organic solvent. The invention also encompasses a highly efficient and atomeconomic process for synthesis of compound [III] i.e. 4-(4-chlorophenyl)cyclohexanone as well as a process for synthesis of 2-[cis-4-(4'- chlorophenyl)cyclohexyl]-3-hydroxy-l,4-naphthoquinone. Further provided is a process for isomerization of cis- Atovaquone i.e. 2-[cis-4-(4'-chlorophenyl)cyclohexyl]-3-hydroxy-l,4- naphthoquinone to tnms-Atovaquone i.e. 2-[trans-4-(4'-chlorophenyl)cyclohexyl]-3- hydroxy- 1,4-naphthoquinone in presence of Lewis acid.

Discovery of 1-amino-4-phenylcyclohexane-1-carboxylic acid and its influence on agonist selectivity between human melanocortin-4 and -1 receptors in linear pentapeptides

Linear pentapeptides (Penta-cis-Apc-DPhe-Arg-Trp-Gly-NH2) containing 1-amino-4-phenylcyclohexane-1-carboxylic acid (cis-Apc) and substituted Apc are potent hMC4R agonists and they are inactive or weakly active in hMC1R, hMC3R, and hMC5R agonist assays. This study, together with our earlier report on 5-BrAtc, demonstrated the importance of replacing His 6 with phenyl-containing rigid templates in achieving good hMC4R agonist potency and selectivity against hMC1R in linear pentapeptides.