32958-56-8

Usage

Uses

Used in Pharmaceutical Synthesis:
(cis)-3,3,5-trimethylcyclohexylamine is used as a building block for the synthesis of pharmaceuticals, contributing to the development of new drugs due to its unique chemical properties and functional groups.
Used in Agrochemical Production:
It is also utilized as an intermediate in the production of agrochemicals, playing a role in the creation of substances that help protect and enhance crop yields.
Used in Specialty Chemicals:
(cis)-3,3,5-trimethylcyclohexylamine is used as a component in the synthesis of specialty chemicals, which are tailored for specific industries and applications.
Used in Rubber Chemicals:
(cis)-3,3,5-trimethylcyclohexylamine is used as an intermediate in the production of rubber chemicals, which are essential for enhancing the properties of rubber materials.
Used in Dyes and Coatings:
(cis)-3,3,5-trimethylcyclohexylamine is employed in the production of dyes and coatings, where its chemical properties contribute to the development of high-quality and durable products.

InChI:InChI=1/C9H19N/c1-7-4-8(10)6-9(2,3)5-7/h7-8H,4-6,10H2,1-3H3/t7-,8+/m1/s1

Upstream product

• 37694-11-4 3,3,5-trimethylcyclohexanone oxime 
• 37690-43-0 trans-3.3.5-Trimethylcyclohexanol-tosylat 
• 134734-56-8 (E)-O-acetyl 3,5,5-trimethyl-2-cyclohexene-1-one oxime 
• 2157-58-6 3,5,5-trimethyl-cyclohex-2-enone oxime 

Downstream Products

• 1803274-65-8 3-(2-{[4-(trifluoromethoxy)phenyl]amino}-1-[(1R,5R)-3,3,5-trimethylcyclohexyl]-1H-benzimidazol-5-yl)propanoic acid 

Relevant academic research and scientific papers

SYNTHESIS AND REACTIONS OF α,β-UNSATURATED AMINES AND THEIR DERIVATIVES. PART VI. ACTION OF DIBORANE ON O-ACETYL 3,5,5-TRIMETHYL-2-CYCLOHEXENE-1-ONE OXIME

The reaction of diborane with O-acetyl 3,5,5-trimethyl-2-cyclohexene-1-one oxime (1) has been examined.The effect of the temperature, molar ratio of substrates and O-acetyl oxime configuration on the stoichiometry and direction of the reaction is described.

REDUCTION OF CONJUGATED CYCLOHEXENONE OXIMES WITH ALUMINIUM HYDRIDE

The reduction of representative conjugated cyclohexenone oximes with aluminium hydride in tetrahydrofuran yields 2-cyclohexenylamines and saturated aziridines - 7-azabicycloheptane derivatives, as the main reaction products.Small quantities of cyclohexylamines and perhydroazepines are also formed.Regioselectivity of the reduction depends on oxime configuration.Higher yields of 2-cyclohexenylamines are obtained from E than Z isomers.The reaction mechanism is proposed.

Stereoselective Reductions of Substituted Cyclohexyl and Cyclopentyl Carbon-Nitrogen ? Systems with Hydride Reagents

Reductions of 3- and 4-substituted cyclohexyl imines, iminium salts, and enamines (via iminium ions) with various hydride reagents reveal that while small reagents (NaBH4, NaBH3CN) favor axial approach as observed with the corresponding ketones, even moderately bulky reagents (i.e., acetoxyboranes) attack preferentially from the equatorial side.This is in direct contrast to the results observed for the same reagents with the corresponding ketones and is interpreted as implying that additional steric interactions induced by the nitrogen substituents encumber axial attack by substituted hydride reagents and force approach from the equatorial direction.The very bulky tri-sec-butylborohydride anion affords highly stereodiscriminating equatorial attack.Reductions of 2-alkylcyclohexyl and 2-alkylcyclopentyl imines and enamines also proceed with high stereoselectivity to give cis-2-alkyl cyclic amines with both hindered and unhindered reagents.This is interpreted to be the result of (1) augmented steric interactions between nitrogen substituents and equatorial 2-alkyl groups (1,3-allylic strain) which induces conformational changes to favor the axial 2-alkyl conformer and (2) hindrance toward equatorial approach by reagents induced by axial alkyl substituents.The result is that equatorial approach is favored with equatorial 2-alkyl conformers and preferential axial approach with axial 2-alkyl conformers, leading to stereoselective production of cis-2-alkylamines. trans-2-n-Propyl-4-tert-butylcyclohexanone is reduced by LiBH(sec-Bu)3 preferentially from the axial direction in contrast to the usual highly selective equatorial attack observed with other cyclohexanones.