1195-42-2

Usage

Uses

Used in Pharmaceutical Industry:
N-ISOPROPYLCYCLOHEXYLAMINE is used as a reagent for the synthesis of 7-hydroxy cannabidiol and cannabidiol-7-oic acid. It plays a crucial role in the production of these compounds, which have potential applications in the medical and pharmaceutical fields due to their therapeutic properties.
Used in Chemical Synthesis:
N-ISOPROPYLCYCLOHEXYLAMINE is also used as a reagent in the synthesis of various other chemicals. Its unique chemical properties make it a valuable component in the creation of different compounds, contributing to the development of new products and materials in the chemical industry.

Synthesis Reference(s)

The Journal of Organic Chemistry, 37, p. 2060, 1972 DOI: 10.1021/jo00978a002

InChI:InChI=1/C9H19N/c1-8(2)10-9-6-4-3-5-7-9/h8-10H,3-7H2,1-2H3/p+1

Upstream product

• 6407-36-9 N-isopropyliden-cyclohexyl amine 
• 108-91-8 cyclohexylamine 
• 67-64-1 acetone 
• 108-94-1 cyclohexanone 
• 75-31-0 isopropylamine 
• 95-47-6 o-xylene 
• 72316-22-4 C₉H₁₈N^(1-)*K⁽¹⁺⁾ 
• 106-42-3 para-xylene 
• 100-41-4 ethylbenzene 
• 19099-48-0 1,1-bis(4-t-butylphenyl)methane 
• 32400-20-7 lithium cyclohexylisopropylamide 
• 4957-14-6 4,4'-dimethyldiphenylmethane 
• 93000-48-7 Methyltriisopropoxyphosphonium tetrafluoroborate 
• 108-88-3 toluene 

Downstream Products

• 52812-84-7 N-Cyclohexyl-N-isopropyl-benzamide 
• 45941-84-2 N-Methyl-N-isopropylamin 
• 42184-44-1 Cyclohexyl-isopropyl-dithiophosphoramidic acid diethyl ester 
• 52702-59-7 2,4-Dibromo-6-[(cyclohexyl-isopropyl-amino)-methyl]-phenol 
• 52702-80-4 2,4-Dichloro-6-[(cyclohexyl-isopropyl-amino)-methyl]-phenol 
• 57375-68-5 N-Isopropoxycarbonyl-3-(N-cyclohexyl-N-isopropylcarbamoyloxy)anilin 
• 64796-74-3 3-[1-(3-Chloro-phenyl)-1-methyl-ethyl]-1-cyclohexyl-1-isopropyl-urea 
• 64796-98-1 3-[1-(4-Chloro-phenyl)-1-methyl-ethyl]-1-cyclohexyl-1-isopropyl-urea 
• 32418-60-3 (Cyclohexyl-isopropyl-amino)-acetic acid ethyl ester 
• 57233-38-2 N-Cyclohexyl-N-isopropyl-butyramide 
• 52702-89-3 4-Chloro-2-[(cyclohexyl-isopropyl-amino)-methyl]-phenol 
• 52702-85-9 4-Bromo-2-[(cyclohexyl-isopropyl-amino)-methyl]-phenol 
• 55413-98-4 N-{4-Acetyl-2-[(cyclohexyl-isopropyl-amino)-methyl]-phenyl}-acetamide 
• 69592-55-8 N-Cyclohexyl-N-isopropyl-4-(2-oxo-1,2-dihydro-quinolin-6-yloxy)-butyramide 

Relevant academic research and scientific papers

Photoredox-mediated C-H functionalization and coupling of tertiary aliphatic amines with 2-chloroazoles

Herein, conditions for C-H functionalization of tertiary aliphatic amines and their subsequent coupling with a number of 2-chloroazole derivatives are reported. The reaction is facilitated by a catalytic amount of tris-fac-Ir(ppy)3, with blue light irradiation and takes place under mild and convenient conditions. Most couplings take place with excellent regioselectivity. The reaction is tolerant of a number of functional groups and allows for rapid access to α-azole carbinamines commonly found in post-translationally modified peptides.

Development of prohibitin ligands against osteoporosis

Current therapeutic approaches to osteoporosis display some potential adverse effects and a limited efficacy on non-vertebral fracture reduction. Some sulfonylamidines targeting the scaffold proteins prohibitins-1 and 2 (PHB1/2) have been showed to inhibit the formation of osteoclasts in charge of bone resorption. Herein, we report the development of a second generation of anti-osteoclastic PHB ligands. The most potent compound, IN45, showed 88% inhibition at the low concentration of 5 μM, indicates that it might serve as a basis for the development of new antiosteoporotic drugs.

Reductive amination of ketones/aldehydes with amines using BH3N(C2H5)3as a reductant

Herein, we report the first example of efficient reductive amination of ketones/aldehydes with amines using BH3N(C2H5)3 as a catalyst and a reductant under mild conditions, affording various tertiary and secondary amines in excellent yields. A mechanistic study indicates that BH3N(C2H5)3 plays a dual function role of promoting imine and iminium formation and serving as a reductant in reductive amination. This journal is

Imine reduction with me2s-bh3

Although there exists a variety of different catalysts for hydroboration of organic substrates such as aldehydes, ketones, imines, nitriles etc., recent evidence suggests that tetra-coordinate borohydride species, formed by activation, redistribution, or decomposition of boron reagents, are the true hydride donors. We then proposed that Me2S-BH3 could also act as a hydride donor for the reduction of various imines, as similar compounds have been observed to reduce carbonyl substrates. This boron reagent was shown to be an effective and chemoselective hydroboration reagent for a wide variety of imines.

Highly efficient one-pot multi-directional selective hydrogenation and N-alkylation catalyzed by Ru/LDH under mild conditions

Atomic economy, non-toxicity, harmlessness and multidirectional selectivity advocated by green chemistry have increasingly become a hot and difficult research topic. Herein, we present a highly efficient, one-pot tandem and easy-to-operate method through which we could directly produce a broad range of multi-directional selective hydrogenated amines or N-alkyl aliphatic amines using aromatic nitro compounds as raw materials. Ru/LDH with characteristics of layered mesoporous structure, well dispersed small Ru nanoparticles and LDH stabilization to the Ru NPs was employed as the catalyst. It is remarkable that multi-directional superb chemoselectivity to aromatic amines, alicyclic amines as well as N-alkyl aliphatic amines could be achieved with excellent catalytic activity and recyclability by tuning reaction conditions over 5wt%Ru/LDH-2. Additionally, this catalytic system also exhibited attractive activity and multi-directional chemoselectivity in the hydrogenation of quinoline and its derivatives with solvents of different polarity. Chemoselectivity to 5,6,7,8-tetrahydroquinoline derivatives could reach as high as 95.6 %.

Photometric Characterization of the Reductive Amination Scope of the Imine Reductases from Streptomyces tsukubaensis and Streptomyces ipomoeae

Imine reductases (IREDs) have emerged as promising enzymes for the asymmetric synthesis of secondary and tertiary amines starting from carbonyl substrates. Screening the substrate specificity of the reductive amination reaction is usually performed by time-consuming GC analytics. We found two highly active IREDs in our enzyme collection, IR-20 from Streptomyces tsukubaensis and IR-Sip from Streptomyces ipomoeae, that allowed a comprehensive substrate screening with a photometric NADPH assay. We screened 39 carbonyl substrates combined with 17 amines as nucleophiles. Activity data from 663 combinations provided a clear picture about substrate specificity and capabilities in the reductive amination of these enzymes. Besides aliphatic aldehydes, the IREDs accepted various cyclic (C4–C8) and acyclic ketones, preferentially with methylamine. IR-Sip also accepted a range of primary and secondary amines as nucleophiles. In biocatalytic reactions, IR-Sip converted (R)-3-methylcyclohexanone with dimethylamine or pyrrolidine with high diastereoselectivity (>94–96 % de). The nucleophile acceptor spectrum depended on the carbonyl substrate employed. The conversion of well-accepted substrates could also be detected if crude lysates were employed as the enzyme source.

Colloid and nanosized catalysts in organic synthesis: XII. Hydrogenation of carbonitriles catalyzed by nickel nanoparticles

Hydrogenation of carbonitriles catalyzed by nickel nanoparticles in isopropanol proceeds under atmospheric pressure of hydrogen within 6-15 h to yield mainly secondary amines. Hydrogenation of α-aminonitriles results in reductive decyanation. β-Aminonitriles undergo hydrogenolysis at the nitrogen-carbon bond.

Supported gold-palladium alloy nanoparticle catalyzed tandem oxidation routes to N-substituted anilines from non-aromatic compounds

In the presence of a supported gold-palladium alloy nanoparticle catalyst (Au-Pd/Al2O3), various kinds of N-substituted anilines can be synthesized from non-aromatic compounds. The observed catalysis is truly heterogeneous, and Au-Pd/Al2O3 can be reused without a significant loss of its catalytic performance.

Design of a bifunctional Ir-Zr based metal-organic framework heterogeneous catalyst for the N-alkylation of amines with alcohols

The direct N-alkylation of amines with alcohols was performed with an Ir-Zr-based metal-organic framework multifunctional heterogeneous catalyst. This system is efficient and environmentally benign for the synthesis of various organic amines in air in the absence of a base. The catalyst was recovered and reused without significant loss of activity, and only water was produced as a byproduct. Better be direct than elusive: The direct N-alkylation of amines with alcohols is performed with an Ir-Zr-based metal-organic framework multifunctional heterogeneous catalyst. This system is efficient and environmentally benign for the synthesis of various organic amines in air in the absence of a base. The catalyst is recovered and reused without significant loss of activity, and only water is produced as a byproduct.

Post-functionalized iridium-Zr-MOF as a promising recyclable catalyst for the hydrogenation of aromatics

The multifunctional heterogeneous catalyst iridium-Zr-based MOF is able to effectively catalyze the hydrogenation of aromatic compounds in high yields under mild conditions. The catalyst was found to be highly active and reusable, giving similar reactivity and selectivity after at least five catalytic uses. This journal is the Partner Organisations 2014.