35018-62-3

Usage

Uses

Used in Pharmaceutical Industry:
(1S-trans)-1,2-Cyclohexanediamine dihydrochloride is used as a pharmaceutical intermediate for the synthesis of various pharmaceutical drugs, contributing to the development of new medications and improving existing ones.
Used in Chiral Ligand and Catalyst Preparation:
(1S-trans)-1,2-Cyclohexanediamine dihydrochloride is used as a chiral building block in the preparation of chiral ligands and catalysts, which are essential in asymmetric synthesis and other enantioselective chemical reactions, enhancing the efficiency and selectivity of these processes.
Used in Specialty Chemical Production:
(1S-trans)-1,2-Cyclohexanediamine dihydrochloride is used in the production of specialty chemicals, where its unique properties and reactivity contribute to the creation of high-value chemical products with specific applications.
Used in Organic Synthesis:
(1S-trans)-1,2-Cyclohexanediamine dihydrochloride is used as a raw material in organic synthesis, providing a versatile starting point for the development of new organic compounds and materials with various applications across different industries.

Upstream product

• 34126-95-9 2-aminocyclohexanecarboxamide 
• 71172-32-2 1,2-dinitrocyclohexane 
• 32044-22-7 (R,R)-1,2-diaminocyclohexane tartrate 
• 116407-32-0 (1R,2R)-(-)-1,2-diammoniumcyclohexane mono-L-(+)-tartrate 
• 32044-22-7 (1R,2R)-1,2-diaminocyclohexane tartrate 
• 87-69-4 L-Tartaric acid 
• 1121-22-8 trans-1,2-Diaminocyclohexane 
• 186144-56-9 N-[(1R,2R)-2-(2-Methoxycarbonyl-acetylamino)-cyclohexyl]-malonamic acid methyl ester 
• 64162-07-8 2-amino-cyclohexanecarboxylic acid ethyl ester 

Downstream Products

• 71172-32-2 1,2-dinitrocyclohexane 
• 327050-72-6 (1R,2R)-N-(2,4-Dinitro-phenyl)-cyclohexane-1,2-diamine 
• 215057-24-2 2,2'-(1E,1'E)-(1R,2R)-cyclohexane-1,2-diylbis(azan-1-yl-1-ylidene)bis(methan-1-yl-1-ylidene)diphenol 
• 96027-57-5 (1R,2R)-N¹-Benzoyl-N²-(2,4-dinitrophenyl)-1,2-cyclohexane diamine 
• 20439-47-8 (1R,2R)-1,2-diaminocyclohexane 
• 1200403-92-4 (1R,2R)-N₁,N₂-bis(pyridin-3-ylmethyl)cyclohexane-1,2-diamine 
• 1383854-72-5 (R,R)-N,N'-bis[(4-dimethylaminophenyl)methyl]-1,2-cyclohexanediamine 
• 193824-05-4 (1R,2R)-N,N’-di(2-hydroxybenzyl)-1,2-diaminocyclohexane 
• 65838-10-0 (1R,2R)-N,N'-dibenzylcyclohexane-1,2-diamine 

Relevant academic research and scientific papers

Cyclic (Alkyl)(amino)carbene Ligand-Promoted Nitro Deoxygenative Hydroboration with Chromium Catalysis: Scope, Mechanism, and Applications

Transition metal catalysis that utilizes N-heterocyclic carbenes as noninnocent ligands in promoting transformations has not been well studied. We report here a cyclic (alkyl)(amino)carbene (CAAC) ligand-promoted nitro deoxygenative hydroboration with cost-effective chromium catalysis. Using 1 mol % of CAAC-Cr precatalyst, the addition of HBpin to nitro scaffolds leads to deoxygenation, allowing for the retention of various reducible functionalities and the compatibility of sensitive groups toward hydroboration, thereby providing a mild, chemoselective, and facile strategy to form anilines, as well as heteroaryl and aliphatic amine derivatives, with broad scope and particularly high turnover numbers (up to 1.8 × 106). Mechanistic studies, based on theoretical calculations, indicate that the CAAC ligand plays an important role in promoting polarity reversal of hydride of HBpin; it serves as an H-shuttle to facilitate deoxygenative hydroboration. The preparation of several commercially available pharmaceuticals by means of this strategy highlights its potential application in medicinal chemistry.

New cyclic aminals derived from rac-trans-1,2-diaminocyclohexane: Synthesis and crystal structure of racemic 1,8,10,12-tetraazatetracyclo[8.3.1.1. 8,1202,7] pentadecane and a route to its enantiomerically pure (R,R) and (S,S) isomers

New enantiomerically pure macrocyclic aminals (2R,7R)- and (2S,7S)-1,8,10,12-tetraazatetracyclo[8.3.1.1.8,120 2,7]pentadecane (4a and 4b) were obtained by a three component reaction between their respective pure enantiomer of trans-1,2- diaminocyclohexane, ammonia, and formaldehyde. Additionally, the X-ray structure of the racemic compound 4 and the specific rotations of the racemic and optically pure compounds were determined. To further understand the synthetic utilities of enantiomers 4a and 4b, Mannich-type reactions with 1H-benzotriazole were performed, affording (3aR,7aR)- and (3aS,7aS)-1,1′-{[2,3,3a,4,5,6,7, 7a-octahydro-1H-1,3-benzimidazole-1,3-diyl]bis(methylene)}bis-1H-benzotriazole (9 and 10) and allowing for new possibilities related to the preparation of chiral ligands for asymmetric catalysis.

SYNTHESIS OF CYCLIC CARBONATES

A dimeric aluminium(salen) catalyst of formula I: herein: Y-Q is CRC1=N or CRC1RC2-NRN1, where RC1, RC2 and RN1 are independently selected from H, halo, optionally substituted C1-20 alkyl, optionally substituted C5-20 aryl, ether and nitro; each of the substituents R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, and R16, is independently selected from H, halo, optionally substituted C1-20 alkyl, optionally substituted C5-20 aryl, optionally substituted C3-20 heterocyclyl, ether and nitro; X1 and X2 are independently either (i) a C2-5 alkylene chain, which is optionally substituted by one or more groups selected from C1-4 alkyl and C5-7 aryl, or a C1-3 bisoxyalkylene chain, which is optionally substituted by one or more groups selected from C1-4 alkyl and C5-7 aryl or (ii) represent a divalent group selected from C5-7 arylene, C5-7 cyclic alkylene and C3-7 heterocyclylene, which may be optionally substituted; (i) (a) at least one of R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, and R16 is selected from L-A, where L is a single bond or a C1-10 alkylene group and A is an ammonium group paired with a counterion selected from Cl, Br and I; and/or (b) at least one of X1 and X2 is a divalent C3-7 heterocyclene group, containing a ring atom which is a quaternary nitrogen atom paired with a counterion selected from Cl, Br and I; and/or (c) at least one of X1 and X2 is a C2-5 alkylene chain or a C1-3 bisoxyalkylene chain, substituted by a group -Q-L-A, where Q is either -C(=O)-O-, -C(=O)-NH-, or a single bond; and/or (ii) (a) one of R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, and R16 is L-A', where L is as defined above and A' is a ammonium linking group bound to a solid support and paired with a counterion selected from Cl, Br and I; or (b) one of X1 and X2 is a divalent C3-7 heterocyclene group, containing a ring atom which is a quaternary nitrogen forming part of an ammonium linking group bound to a solid support and paired with a counterion selected from Cl, Br and I; or (c) one of X1 and X2 is a C2-5 alkylene chain or a C1-3 bisoxyalkylene chain, substituted by a group -Q-L-A'.

Instantaneous low temperature gelation by a multicomponent organogelator liquid system based on ammonium salts

A new synergistic multicomponent organogelator liquid system (MOGLS) was discovered during the standard protocol of tartaric acid-mediated racemic resolution of (±)-trans-1,2-diaminocyclohexane. The MOGLS is formed by a 0.126 M methanolic solution of (1R,2R)-(+)-1,2-diaminocyclohexane L-tartrate and 1 equiv of concentrated hydrochloric acid. Nonreversible gelation of oxygenated and nitrogenated solvents occurs efficiently at low temperature. Several features make this system unique: (1) it is a multicomponent solution where each of the five components is required for the organogelation property; (2) the multicomponent organogelator liquid system (MOGLS) is formed by simple, small, and commercially available chiral building blocks dissolved in a well-defined solvent system (MeOH/HCl/H2O); (3) the chiral building blocks are easily amenable for further modifications in structure-property relationship studies; (4) the gelation phenomenon takes place efficiently at low temperature upon warming up the isotropic solution, conversely to the typical gel preparation protocol (gel formation upon cooling down the isotropic solution); (5) the formed organic gels are not thermoreversible in spite of the noncovalent interactions that hold the 3D-fibrillar network together.

SYNTHESIS OF CYCLIC CARBONATES IN THE PRESENCE OF DIMERIC ALUMINIUM (SALEN) CATALYSTS

A process for the production of cyclic carbonates comprising contacting an epoxide with carbon dioxide in the presence of a dimeric aluminium(salen) catalyst, and a co-catalyst capable of supplying Y-, where Y is selected from Cl, Br and I, where the dimeric aluminium(salen) catalyst is of formula I:

De novo synthesis of tamiflu via a catalytic asymmetric ring-opening of meso-aziridines with TMSN3

An asymmetric ring-opening reaction of meso-aziridines with TMSN3 was developed using a catalyst prepared from Y(OiPr)3 and chiral ligand 2 in a 1:2 ratio. Excellent enantioselectivity was realized from a wide range of substrates with a practical catalyst loading. The products were efficiently converted to enantiomerically enriched 1,2-diamines, which are versatile chiral building blocks for pharmaceuticals and chiral ligands. This reaction was applied to a catalytic asymmetric synthesis of Tamiflu, a very important anti-influenza drug containing a chiral 1,2-diamino functionality. Copyright

A chiral sensor for arginine and lysine

(Graph presented) We provide access to a new class of C1-or C2-symmetrical host molecules 1 and 2 based on a spirobisindane skeleton. Whereas 1 is selective for short, rigid diamines, 2 prefers longer α,ω-dications. Of all the amino acid methyl esters, only those of lysine and arginine with the correct distance between their cationic groups form strong 1:1 complexes in DMSO with 2. NMR titrations reveal high association constants as well as discrimination between the enantiomers of lysine and arginine.

Chemoenzymatic syntheses of two optically active hexa-azamacrocycles

Two optically active hexa-azamacrocycles with C2 and D2 symmetry, respectively, have been efficiently synthesized from the enzymatically prepared (R,R)-cyclohexane-1,2-diamine bis(amidoester) derivative (R,R)-4.

Enantioselective addition of diethylzinc to benzaldehyde catalyzed by chiral titanate complexes with helical ligands

Enantioselective alkylation of benzaldehyde with Et2Zn has been studied. This reaction is catalyzed by helical titanium complexes of tetradentate ligands and has been found to give good to excellent enantioselectivities.