32044-22-7

Usage

Uses

Used in Pharmaceutical Industry:
(1R,2R)-(+)-1,2-CYCLOHEXANEDIAMINE L-TARTRATE is used as a chiral resolving agent for the separation and purification of racemic mixtures. Its chiral nature allows for the production of pure enantiomers, which are essential in the development of pharmaceuticals with specific therapeutic effects and reduced side effects.
Used in Coordination Chemistry:
In the field of coordination chemistry, (1R,2R)-(+)-1,2-CYCLOHEXANEDIAMINE L-TARTRATE serves as a ligand in metal complexes. Its unique structure and properties enable the formation of stable complexes with various metal ions, which can be utilized in a range of applications, including catalysis and the development of new materials.

Upstream product

• 87-69-4 L-Tartaric acid 
• 1121-22-8 trans-1,2-Diaminocyclohexane 
• 147-71-7 D-tartaric acid 
• 694-83-7 rac-diaminocyclohexane 
• 20439-47-8 (1R,2R)-1,2-diaminocyclohexane 
• 138508-61-9 L-(-)-tartaric acid 
• 64-19-7 acetic acid 

Downstream Products

• 1421697-46-2 (S)-2-(3-((1S,2S)-2-aminocyclohexyl)thioureido)-N-benzhydryl-N,3,3-trimethylbutanamide 
• 21436-03-3 (S,S)-1,2-diaminocyclohexane 
• 284497-48-9 (1S,2S)-N,N'-bis-pyridin-2-ylmethylene-cyclohexane-1,2-diamine 
• 81748-00-7 N,N'-bis(pyridin-2-ylmethyl)-(S,S)-1,2-cyclohexanediamine 
• 143585-47-1 (R,R)-1,2-bis(tosylamino)cyclohexane 
• 98795-02-9 (R,R)-N,N'-bis(2-hydroxy-3-tert-butyl-benzylidene)-1,2-diaminocyclohexane 
• 182368-90-7 (R,R)-N,N'-bis(3-tert-butyl-5-methylsalicylidene)-1,2-cyclohexanediamine 
• 951153-76-7 N,N′-((1R,2R)-cyclohexane-1,2-diyl)bis(benzene-1,2-diamine) 
• 174291-96-4 (1R,2R)-(-)-N-p-tosyl-1,2-cyclohexanediamine 
• 135616-40-9 (R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine 
• 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 
• 1315511-05-7 (1R,2R)-[N,N'-bis(2'-hydroxy-5'-tert-butylbenzylidene)]-1,2-diaminocyclohexane 

Relevant academic research and scientific papers

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.

Copolymerization of carbon dioxide and propylene oxide catalyzed by two kinds of bifunctional salen-cobalt(III) complexes bearing four quaternary ammonium salts

Two new bifunctional salen-cobalt(III) complexes were synthesized, which consist of salicylaldehyde bearing four quaternary ammonium salts and two different diamines. The copolymerization results indicated that decreasing temperature is advantageous for both the complexes. Of both the diamines, the complex 9 with o-diaminobenzene has a higher catalytic effect compared to complex 6 with 1,2-diaminocyclohexane. The catalytic effect of complex 9 is over 3.5 times than that of complex 6 at a temperature of 30°C. The research of PCO2 on the copolymerization revealed that the first-rank pressure was at 2 MPa for the two complexes. The highest turnover number are under conditions of T = 30°C, PCO2 = 2 MPa, and t = 24 hr. Differential scanning calorimeter curves indicated that poly(propylene carbonate) (PPC) by complex 9 has the highest Tg of 54.2°C. DTGA curves showed that there were two thermal degradation peaks, the first is for the ester bond, and the second is for the C–C bond.

Design and synthesis of cage-like NADH model molecule intermediate with multi-chiral centers

Studying NADH molecules is one of the most active areas in biomimetic research. It is important to design novel and efficient chiral NADH model molecules. Herein, a cage-like NADH model with multi-chiral centers was designed, and key intermediates have been synthesized. In this study, we found that pentafluorophenoxy group is an excellent leaving group for our synthetic route.

Spectroscopic exploration of binding of new imidazolium-based palladium(II) saldach complexes with CT-DNA as anticancer agents against HER2/neu overexpression

The HER2/neu has shown a potential role in the choice of active chemotherapy for breast tumors because of its prognostic relevance and putative role in predicting drug resistance. Moreover, suppressing DNA replication has become an attractive strategy for treating cancer patients. In this attempt, the present study aimed to prepare new series of bis-imidazolium-based saldach {H2(Et)2saldach (nBu-Im+-X–)2} and their cis-Pd(II) complexes (saldach = N,N′-bis-(salicylidene)-R,R-1,2-diaminocyclohexane; X = Cl, PF6, BF4) as anticancer agents. The in vitro cytotoxicity activity of new cis-Pd(II) complexes against human breast adenocarcinoma cell lines (MCF-7) revealed higher growth-inhibitory effect than the native ligands. They induced a significant decrease for the protein HER2/neu expression with p 50 = 8.5 ± 0.2 μM) in inhibition of cell proliferation. Additionally, in vitro studies of Pd(II) complex (5a) using UV–Vis spectroscopy and binding affinity toward the calf thymus (CT) DNA) showed a combination of covalent, intercalation, hydrogen bonding interactions through formation of (CT-DNA).

Preparation method and application of trans-cyclohexanediamine tartrate

The invention provides a preparation method of trans-cyclohexanediamine tartrate. The preparation method comprises the steps of charging, dropwise adding of trans-cyclohexanediamine, dropwise adding of glacial acetic acid, heat-insulation reaction and cooling. The invention further provides application of the trans-cyclohexanediamine tartrate in preparation of a schiff base metallic cobalt complex. The specific rotation of the prepared trans-cyclohexanediamine tartrate is minus 11 degrees to minus 13 degrees, the content is greater than or equal to 98.0%, and the appearance of the trans-cyclohexanediamine tartrate is off-white or light yellow crystal. The yield of the prepared trans-cyclohexanediamine tartrate is 55.8-56%; and reaction conditions are mild, and the preparation method is simple to operate, is carried out under normal pressure, and is high in safety.

Synthesis of N,N′-Dialkylated Cyclohexane-1,2-diamines and Their Application as Asymmetric Ligands and Organocatalysts for the Synthesis of Alcohols

A series of N,N′-dialkylated derivatives of (1R,2R)-cyclohexane-1,2-diamine were synthesized, and a new approach to the one-pot preparation of this type of amine was demonstrated. The prepared diamines were used as organocatalysts for the two-step synthesis of α-hydroxy γ-keto esters from arenes, chlorooxoacetates, and ketones; they were also used as chiral ligands for Meervein-Ponndorf-Verley reductions and Henry reactions.

A novel water-soluble highly selective “switch-on” ionic liquid-based fluorescent chemi-sensor for Ca(II)

A novel chemi-sensor involve new bis-ionic Schiff base sensor (BISBS), N,N′-bis-[5-((2,4-lutidiniumchloride)methylene)-3-methoxysalicylidene]-R,R-1,2-cyclohexanediimine, has been synthesized and characterized. BISBS chemi-sensor was designed based on internal charge transfer (ICT) fluorescence mechanism. This new water soluble chemi-sensor provides great selectivity fluorescence detection for Ca(II) ions in an important physiological pH range. Moreover, the interaction of Ca(II) with the deprotonated BISBS to produce a metal-ligand complex with a ratio of (1: 1) accompanying with an enhancement in the intensity of emission band located at 502?nm. Fluorescence switching-on during the chemical interaction between BISBS and Ca(II) ions is very easily noticed with naked eye, but other metal cations such as alkali, alkaline earth and transition metal don't give any fluorescence changes. The novel developed BISBS sensor successively offers low limit of detection (LOD) 1.5?nM and fast tracing of Ca(II) in the physiological pH?7.6. Thus BISBS may provide a novel auspicious methodology for detection calcium cations in the environmental and biological samples.

Asymmetric Grignard Synthesis of Tertiary Alcohols through Rational Ligand Design

A simple, general and practical method is reported for highly enantioselective construction of tertiary alcohols through the direct addition of organomagnesium reagents to ketones. Discovered by rational ligand design based on a mechanistic hypothesis, it has an unprecedented broad scope. It utilizes a new type of chiral tridentate diamine/phenol ligand that is easily removed from the reaction mixture. It is exemplified by application to a formal asymmetric synthesis (>95:5 d.r.) of vitamin E.

METHOD OF PRODUCING OPTICALLY ACTIVE TRANS-1,2-DIAMINOCYCLOHEXANE

A method produces optically active trans-1,2-diaminocyclohexane, in which a crystal of optically active trans-1,2-diaminocyclohexane is obtained by crystallization from a solution of optically active trans-1,2-diaminocyclohexane. Optically active trans-1,2-diaminocyclohexane with high purity is obtained in a favorable yield from a solution of optically active trans-1,2-diaminocyclohexane. The optically active trans-1,2-diaminocyclohexane with high purity is useful as a raw material for a large number of medicines.

Preparation of C 2-Symmetric Biaryl Bisiminium Salts and Their Use as Organocatalysts for Asymmetric Epoxidation

Two C 2-symmetric bisiminium salt species containing biphenylazepinium units and derived from two chiral diamines were prepared and tested as organocatalysts for asymmetric epoxidation.