29456-22-2

Upstream product

• 100-64-1 cyclohexanone-oxime 
• 98-88-4 benzoyl chloride 
• 4231-62-3 1-benzoyl-1H-benzotriazole 
• 1122-60-7 1-nitrocyclohexane 
• 65-85-0 benzoic acid 
• 108-94-1 cyclohexanone 

Downstream Products

• 105-60-2 caprolactam 
• 7015-50-1 2-amino-2-phenylcyclohexan-1-one 

Relevant academic research and scientific papers

Structure-activity relationships for the anaesthetic and analgaesic properties of aromatic ring-substituted ketamine esters

A series of benzene ring substituted ketamine N-alkyl esters were prepared from the corresponding substituted norketamines. Few of the latter have been reported since they have not been generally accessible via known routes. We report a new general route to many of these norketamines via the Neber (oxime to α-aminoketone) rearrangement of readily available substituted 2-phenycyclohexanones. We explored the use of the substituents Cl, Me, OMe, CF3, and OCF3, with a wide range of lipophilic and electronic properties, at all available benzene ring positions. The 2- and 3-substituted compounds were generally more active than 4-substituted compounds. The most generally acceptable substituent was Cl, while the powerful electron-withdrawing substituents CF3 and OCF3 provided fewer effective analogues.

Transition-Metal-Promoted Direct C?H Cyanoalkylation and Cyanoalkoxylation of Internal Alkenes via Radical C?C Bond Cleavage of Cycloketone Oxime Esters

Transition-metal-catalyzed alkyl-Heck-type cross-coupling of olefinic C?H bonds has been a challenge in the C?H activation area. Herein, we report FeCl3-promoted efficient direct C?H cyanoalkylation of internal alkenes, that is, ketene dithioacetals, with cycloketone oxime esters via radical C?C bond cleavage under the redox-neutral conditions. With CuCl2 as the catalyst under a dioxygen atmosphere direct C?H cyanoalkoxylation of the same internal alkenes was achieved. The cyanoalkylated tetrasubstituted alkene products could be diversely transformed to cyanoalkyl-funtionalized N- and S-heterocyclic compounds. The mechanistic studies have revealed that these C?H cyanoalkylation and cyanoalkoxylation reactions proceed through a radical pathway. (Figure presented.).

Sequential [3,3]-Sigmatropic Rearrangement/Nucleophilic Arylation of N -(Benzoyloxy)enamides towards the Preparation of Cyclic β-Aryl-β-amino Alcohols

A new method has been developed for the efficient synthesis of cyclic β-aryl-β-amino alcohol derivatives bearing a tetrasubstituted carbon center via the [3,3]-sigmatropic rearrangement of N-(benzoyl oxy)enamides followed by nucleophilic arylation reactio

A convenient practical synthesis of alkyl and aryl oxime esters

A facile access to the synthesis of alkyl and aryl oxime esters of ketoximes and aldoximes in high yields (90-97%) is reported. The reactions were performed using N-[3-(methylamino)propyl]-N′-ethylcarbodiimide hydrochloride (EDCI) reagent in the presence of 4-(dimethylamino)pyridine (DMAP) as a catalyst at room temperature. The isolation and purification of products is very simple and in cases where product is solid, column chromatography is avoided. Georg Thieme Verlag Stuttgart New York.

A novel synthesis of carboxylic acid oxime esters catalyzed by 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate

We describe a facile synthesis of carboxylic acid oxime esters in acetonitrile from the corresponding carboxylic acids and oximes catalyzed by 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate in the presence of triethylamine at room temperature under mild conditions.

Preparative synthesis of cyclohexanone oxime esters

Preparative procedures have been developed for the synthesis of cyclohexanone oxime esters by acylation of cyclohexanone oxime with carboxylic acid anhydrides in the presence of perchloric acid or with carboxylic acid chlorides in the presence of pyridine

α-nitro ketone synthesis using N-acylbenzotriazoles

Readily available N-acylbenzotriazoles 2a-1 (derived from a variety of aliphatic, (hetero)aromatic, and N-protected α-amino carboxylic acids) smoothly convert primary 3a-c and α-functionalized primary nitroalkanes 3d into the corresponding α-nitro ketones

Reaction of Trimethylsilyl Azide with C=N-O Bond

Trimethylsilyl azide (TMSA) was reacted with an oxime ester or a Reissert salt in the presence of trimethylsilyl trifluoromethanesulfonate to give tetrazole derivative.The details of these reactions are examined.