6740-66-5

Upstream product

• 110480-94-9 cyclopentylphenylmethanol 
• 100-47-0 benzonitrile 
• 5422-88-8 phenyl cyclopentyl ketone 

Downstream Products

• 35099-68-4 2-(2-Hydroxyaethylamino)-2-phenylcyclohexanon 
• 948565-98-8 S-(1-Benzoylcyclopentyl) 6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-propionyloxyandrosta-1,4-diene-17β-carbothioate 
• 1427182-73-7 2-phenyl-2-(phenylethynyl)-1-oxaspiro[2.4]heptane 
• 1427182-75-9 2-((4-methoxyphenyl)ethynyl)-2-phenyl-1-oxaspiro[2.4]heptane 
• 1427182-83-9 trimethyl((2-phenyl-1-oxaspiro[2.4]heptan-2-yl)ethynyl)silane 
• 1427182-77-1 2-(hex-1-yn-1-yl)-2-phenyl-1-oxaspiro[2.4]heptane 
• 1427182-79-3 2-(dec-1-yn-1-yl)-2-phenyl-1-oxaspiro[2.4]heptane 
• 1427182-81-7 2-(cyclopropylethynyl)-2-phenyl-1-oxaspiro[2.4]heptane 
• 1427182-74-8 2-phenyl-2-(phenylethynyl)cyclohexanone 
• 1427182-91-9 1-(1-methoxy-1,3-diphenylprop-2-yn-1-yl)cyclopentanol 
• 1427182-76-0 2-((4-methoxyphenyl)ethynyl)-2-phenylcyclohexanone 
• 1427182-84-0 2-phenyl-2-((trimethylsilyl)ethynyl)cyclohexanone 
• 1427182-78-2 2-(hex-1-yn-1-yl)-2-phenylcyclohexanone 
• 1427182-82-8 2-(cyclopropylethynyl)-2-phenylcyclohexanone 

Relevant academic research and scientific papers

ARYLCYCLOHEXYLAMINE DERIVATIVES AND THEIR USE IN THE TREATMENT OF PSYCHIATRIC DISORDERS

Provided herein are arylcyclohexylamine derivatives and their use in the treatment of psychiatric disorders.

Access to α-Cyano Carbonyls Bearing a Quaternary Carbon Center by Reductive Cyanation

Reductive cyanation of tertiary alkyl bromides using electrophilic cyanating reagent and zinc reductant was developed, providing various α-cyano ketones, esters, and carboxamides containing a nitrile-bearing all-carbon quaternary center in good to excellent yields under mild reaction conditions. The corresponding reaction mechanism involving in situ generated organozinc reagent and reactivity distinction was elucidated by density functional theory computation.

Catalytic Asymmetric Acyloin Rearrangements of α-Ketols, α-Hydroxy Aldehydes, and α-Iminols by N, N′-Dioxide-Metal Complexes

A highly enantioselective acyloin rearrangement of cyclic α-ketols has been developed with a chiral Al(III)-N,N′-dioxide complex as catalyst. This strategy provided an array of optically active 2-acyl-2-hydroxy cyclohexanones in moderate to good yields with high enantioselectivities. The asymmetric isomerizations of acyclic α-hydroxy aldehydes and α-iminols were achieved as well under modified conditions, affording the corresponding chiral α-hydroxy ketones and α-amino ketones in moderate results. Moreover, further transformations of product to enantioenriched diols were carried out.

Iron-Catalyzed Acyl Migration of Tertiary α-Azidyl Ketones: Synthetic Approach toward Enamides and Isoquinolones

This paper reports that tertiary α-azidyl phenyl ketones can be transformed into enamides by treatment with FeBr2 at elevated temperature in DMF. The reaction proceeds via 1,2-benzoyl migration from α-carbon to the nitrogen atom, accompanied by expulsion of a nitrogen molecule. This protocol is suitable for the synthesis of N-(cyclopent-1-en-1-yl)benzamides, N-(cyclohex-1-en-1-yl)benzamides, and N-benzoyl-α-methyl enamines and provides a convenient approach toward isoquinolones.

Synthesis, absolute configuration and in vitro cytotoxicity of deschloroketamine enantiomers: rediscovered and abused dissociative anaesthetic

In this study, we aim to determine differences in cytotoxicity of racemic deschloroketamine and its enantiomers. The synthesized racemate of this recently rediscovered and abused dissociative anaesthetic was resolved by chiral HPLC and the absolute configuration of the enantiomers was assigned using a combination of circular dichroism methods and single-crystal X-ray. Not only the absolute configuration, but also the most preferred conformers present in the crystal were successfully determined by electron and vibrational circular dichroism supported by ab initio calculations, and confirmed by X-ray. The in vitro cytotoxicity of racemic deschloroketamine and its enantiomers was determined for nine different types of cell lines. Generally, (S)-deschloroketamine exhibited higher cytotoxicity in the majority of cases. For human embryonic kidney cells (HEK 293T), the (S)-enantiomer reached the IC50 below 1 mM concentration and, in consequence, proved to be twice as potent as the (R)-enantiomer. On the other hand, live-cell fluorescence microscopy imaging at sub-IC50 concentrations provided evidence for only a minor effect of deschloroketamine racemate and enantiomers on endoplasmic reticulum stress and mitochondria morphology in neuroblastoma cells SH-SY5Y.

Unexpected Role of p-Toluenesulfonylmethyl Isocyanide as a Sulfonylating Agent in Reactions with α-Bromocarbonyl Compounds

The reactions of p-toluenesulfonylmethyl isocyanide (TosMIC) with α-bromocarbonyl compounds leading efficiently to α-sulfonated ketones, esters, and amides were reported, in which an explicit new role of TosMIC as the sulfonylating agent was uncovered for the first time. Mechanistic study by control experiments and DFT calculations suggested that the reaction is initiated by Cu(OTf)2-catalyzed hydration of TosMIC to form a formamide intermediate, which undergoes facile C-S bond cleavage under the mediation of a Cs2CO3 additive.

Building Congested Ketone: Substituted Hantzsch Ester and Nitrile as Alkylation Reagents in Photoredox Catalysis

For the first time, 4-alkyl Hantzsch esters were used to construct molecules with all-carbon quaternary centers by visible light-induced photoredox catalysis via transfer alkylation. Up to a 1500 h-1 turnover frequency was achieved in this reaction. Reactions of 4-alkyl Hantzsch nitriles as tertiary radical donors joined two contiguous all-carbon quaternary centers intermolecularly, and this chemistry was used to synthesize a common precursor of a class of hydroxysteroid dehydrogenase inhibitors.

An alternative reaction outcome in the gold-catalyzed rearrangement of 1-alkynyloxiranes

The gold(III)-catalyzed rearrangement of tetrasubstituted 1-alkynyloxiranes is described. This transformation led to a different reaction outcome with respect to related substrates previously studied. Thus, tertiary α-alkynylketones or alkynols can be selectively obtained. Moreover, gold(III) proved capable to catalyze the rearrangement of simple epoxides. These results indicate that gold(III) complexes act as oxophilic Lewis acids rather than π-acids in these transformations.

THERAPEUTIC AGENT FOR DIABETES

A therapeutic agent for diabetes, which comprises a compound of the formula [I] wherein Xis a group of the formula wherein R4and R5are the same or different and each is a hydrogen atom, an optionally substituted alkyl having 1 to 5 carbon atoms and the like, and R6is a hydrogen atom or an amino-protecting group; R1is an optionally substituted alkyl having 1 to 5 carbon atoms, an optionally substituted alkenyl having 2 to 6 carbon atoms and the like, R2is a hydrogen atom, an optionally substituted alkyl having 1 to 5 carbon atoms and the like, R2' is a hydrogen atom, and R3is an optionally substituted alkyl having 1 to 5 carbon atoms and the like, a prodrug thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof and a solvate thereof. The compound of the present invention shows superior blood sugar decreasing action on the state of hyperglycemia, but does not affect the blood sugar when it is in the normal range or in the hypoglycemic state, which means that it is free of serious side effects such as hypoglycemia. Therefore, the compound of the present invention is useful as a therapeutic drug for diabetes and also useful as a preventive of the chronic complications of diabetes.