Cyclohexylamine derivatives

A)Ai-dicyclohexyl-2-benzotliiazolesulfenamide (42) [4979-32-2], The cyclohexylamine derivative is preferred over /n/ butylamine [75-64-9] and morpholine sulfenamide analogues because of lower amine volatility and less nitrosamine risk respectively. 

Bromocresol green (3.8...5.4) aliphatic carboxylic acids[103,187 — 204] triiodobenzoic acid [205], derivatives of barbituric acid [206] amphetamine derivatives [207, 208] phenazones, morazone [209] alkaloids [91, 209] nephopam [210] phenyramidol metabolites [211] diethylalkylacetamide derivatives [212] zipeprol (Mirsol) [213] thalidomide and hydrolysis products [214] cyclohexylamine derivatives [215] herbicide residues [216]... 

Vapor phase inhibitors These are used for the temporary protection of new plant in transit or prior to commissioning. Volatile corrosion inhibitors such as cyclohexylamine derivatives are used. The plant must be sealed or contained to prevent rapid loss of the inhibitor. Sachets of these materials are placed in packing cases. Papers impregnated with them are available for wrapping steel items. These inhibitors are used primarily to protect steel. 

Analysis of the above product for carbon, hydrogen, nitrogen, inositol, and phosphorus gave values corresponding to the cyclohexylamine derivative. It had a melting point of 124-126°C. 

Kloog, Y., Rehavi, M., Maayani, S., Sokolovsky, M. (1977). Anticholinesterase and antiacetylcholine activity of 1-phen-cyclohexylamine derivatives. Eur. J. Pharmacol. 45 221-7. 

Cyclohexylamine, hydroxylamine, semicarbazide, (p-nitrophenyl)hy-drazine and (2,4-dinitrophenyl)hydrazine, and isonicotinoylhydrazine gave derivatives (18) of the free dialdehyde. Reduction of the cyclohexylamine derivative occurred with elimination of a molecular proportion of amine, to give the heterocyclic compound (19). The above reactions proved the existence of an equilibrium between the dialdehyde and the hemialdal forms in solution. 

In a further example, a biocatalytic route for the production of optically pure 3-substituted cyclohexylamine derivatives from prochiral bicychc P-diketones was established by employing three biocatalytic reaction steps (Scheme 4.16) [53]. The sequence combined the stereoselective hydrolysis of a C-C bond catalyzed by a P-diketone hydrolase [54] (6-oxocamphor hydrolase (OCH) from Rhodococcus sp. [55]), followed by an Upase-catalyzed esterification [Candida antarctica lipase B (CAL-B), Novozyme 435], and a subsequent asymmetric amination by either an (S)-or (1 )-selective m-TA [V.fluvialis [27] or a variant of the Arthrobacter sp. TA [16a] (ArRmutll)]. 

Scheme 4.16 Diastereoselective production of 3-substituted cyclohexylamine derivatives via a linear cascade combining three enzymatic steps.

Table 4.5 Selected results of the investigated three-step cascade reaction providing 3-substitued cyclohexylamine derivatives.

Subsequently, the same group disclosed that in the presence of 10mol% of 5b, diketones 39, primary amine 40, and Hantzsch ester 37b could also undergo a cascade aldol-reduction reaction to provide cyclohexylamine derivatives 41 with up to 96% ee (Scheme 2.11) [18]. 

Diastereoselective preparation of 3-substituted cyclohexylamine derivatives using two hydrolases and one co-TA. 

Hydrolases were also successfully coupled with co-TAs for the production of 3-cyclohexylamine derivatives from prochiral bicyclic diketones (Scheme 2.17) [41]. The reaction sequence was based on three biocatalytic steps— namely, stereoselective hydrolysis of a C—C bond using a p-diketone hydrolase (6-oxocamphor hydrolase (OCH) from Rhodococcus sp.), followed by Candida antarctica lipase B (C AL-B)-catalyzed esterification, and finally asymmetric amination by stereocomplementary (R)-selective ArRmutll or (S)-selective VF-co-TA. The first two reactions were performed simultaneously in an organic solvent (diisopropyl etirer H O MeOH 97.5/2.5/1). The ami-nation step could also be conducted in an organic solvent after removing the hydrolases by filtration, avoiding the change of the reaction media. 

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