320778-92-5

Usage

Uses

Used in Chemical Synthesis:
1,2-Cyclohexanediamine,N,N-dimethyl-,(1R,2R)-(9CI) is used as a chiral amine catalyst for asymmetric direct aldol and Michael addition reactions. Its application in these reactions is crucial for the synthesis of complex organic molecules with high enantioselectivity and yield, which is essential in the pharmaceutical and fine chemicals industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,2-Cyclohexanediamine,N,N-dimethyl-,(1R,2R)-(9CI) is used as a key intermediate in the synthesis of various drugs and drug candidates. Its ability to act as a chiral amine catalyst allows for the production of enantiomerically pure compounds, which is vital for the development of effective and safe medications.
Used in Fine Chemicals Industry:
1,2-Cyclohexanediamine,N,N-dimethyl-,(1R,2R)-(9CI) is also utilized in the fine chemicals industry for the production of specialty chemicals, fragrances, and flavors. The chiral nature of 1,2-Cyclohexanediamine,N,N-dimethyl-,(1R,2R)-(9CI) enables the creation of high-quality enantiomerically pure products, which are in high demand for various applications.
Used in Research and Development:
In the field of research and development, 1,2-Cyclohexanediamine,N,N-dimethyl-,(1R,2R)-(9CI) serves as an important tool for studying the mechanisms of asymmetric catalysis and the development of new synthetic methods. Its unique properties make it a valuable asset in advancing the understanding of chemical reactions and the design of novel catalysts.

Upstream product

• 67198-21-4 (±)-N,N-dimethyl-trans-1,2-diaminocyclohexane 
• 34218-57-0 (R,R)-trans-N-[2-(N',N'-dimethylamino)hexyl]acetamide 
• 877677-96-8 N-[(1R,2R)-2-(dimethylamino)cyclohexyl]benzamide 
• 1234860-01-5 (1R,2R)-N₁,N₁-dimethylcyclohexane-1,2-diamine bishydrochloride 
• 931-16-8 (+/-)-trans-2-aminocyclohexanol 
• 286-18-0 7-azabicyclo[4.1.0]heptane 

Downstream Products

• 38383-49-2 (1R,2R)-bis(dimethylamino)cyclohexane 
• 620960-26-1 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea 
• 820242-14-6 1-((1R,2R)-2-N,N-dimethylaminocyclohexyl)-3-(3,5-bis(trifluoromethyl)phenyl)urea 
• 919113-01-2 1-{(S)-1-(benzylcarbamoyl)-2,2-dimethylpropyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea 
• 919112-93-9 1-{(1R,2R)-2-(dimethylamino)cyclohexyl}-3-(pyridine-3-yl)thiourea 
• 919112-92-8 1-{(1R,2R)-2-(dimethylamino)cyclohexyl}urea 
• 852202-59-6 1-{(R)-1-(N-benzyl-N-methylcarbamoyl)-2,2-dimethylpropyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea 
• 919113-03-4 1-{(S)-1-(N-benzyl-N-methylcarbamoyl)-3,3-dimethylbutyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea 
• 1020665-66-0 (1R,2R)-2-isothiocyanato-N,N-dimethylcyclohexanamine 
• 849024-91-5 1-{(1R,2R)-2-(dimethylamino)cyclohexyl}-3-mesitylurea 
• 919112-95-1 1-adamantan-1-yl-3-{(1R,2R)-2-dimethylaminocyclohexyl}thiourea 
• 849024-93-7 1-(3,5-dinitrophenyl)-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}urea 
• 852202-53-0 1-{(1R,2R)-2-(dimethylamino)cyclohexyl}-3-{(R)-1-phenylethyl}urea 

Relevant academic research and scientific papers

Synthesis, resolution, and absolute configuration of trans-1-amino-2-dimethylaminocyclohexane

Racemic trans-1-amino-2-dimethylaminocyclohexane was prepared by aziridine ring opening reaction of 7-azabicyclo[4.1.0]heptane with HNMe2. The resolution of the racemate was accomplished by crystallization as the L-tartrate. The optical purity

A new chiral primary-tertiary diamine-Bronsted acid salt organocatalyst for the highly enantioselective direct anti-aldol and syn-Mannich reactions

A new primary-tertiary diamine catalyst is easily prepared in a few steps from inexpensive, commercially available, enantiopure materials. This organocatalyst can be effective catalyzed the direct asymmetric aldol and Mannich reactions. The anti-aldol products can be obtained with up to a 99:1 anti/syn ratio and >98 % ee, while the syn-Mannich products could be obtained with up to a 99:1 syn/anti ratio and >99 % ee. Catalyst 1c can be used efficiently on a large scale with the enantioselectivities of the anti-aldol and syn-Mannich reactions being maintained at the same level, which offers a great possibility for application in industry.

The first catalytic, enantioselective aza-Henry reaction of an unactivated cyclic imine

The aza-Henry reaction is an efficient route to important chiral, vicinal diamines. Reports of the asymmetric version typically use electron-deficient acyclic imines. We report the first example of a catalytic, asymmetric aza-Henry reaction on an unfunctionalized cyclic imine that gives access to enantiopure diamine derivatives under experimentally straightforward conditions. The stereocentre is established through the initial nitromethane addition to the imine. The scalemic intermediate may be trapped through acylation, then crystallized. Copyright

Design and development of bioinspired guanine-based organic catalyst for asymmetric catalysis

Design, preparation, and studies of a family of new organic catalysts are presented. The design of the catalysts is inspired by the ability of DNA nucleobases to develop precise and explicit hydrogen bonds. We have shown that this phenomenon can be used to create a useful organic catalyst that demonstrates a recognition pattern similar to those of common organic substrates. A selected bifunctional catalyst based on a guanine structure has been shown to catalyze the conjugate addition of 1,3-dicarbonyl compounds to various nitroalkenes, providing the products in good yields and enantioselectivities.

A simple primary-tertiary diamine-Bronsted acid catalyst for asymmetric direct aldol reactions of linear aliphatic ketones

Compared with the well-explored enamine catalysis with secondary amines, the development of efficient enamine-based primary amine catalysts has remained as an elusive goal until recently. We present herein that a simple chiral primary-tertiary diamine 1d

Structural optimization of thiourea-based bifunctional organocatalysts for the highly enantioselective dynamic kinetic resolution of azlactones

This article describes the synthesis of a library of structurally diverse bifunctional organocatalysts bearing both a quasi-Lewis acidic (thio)urea moiety and a Bronsted basic tertiary amine group. Sequential modification of the modular catalyst structure and subsequent screening of the compounds in the alcoholytic dynamic kinetic resolution (DKR) of azlactones revealed valuable structure-activity relationships. In particular, a "hit-structure" was identified which provides e.g. N-benzoyl-tert-leucine allyl ester in an excellent enantiomeric excess of 95%. The Royal Society of Chemistry 2006.

Facile monoprotection of trans-1,2-diaminocyclohexane

A new method of monoprotection of C2-symmetric trans-1,2-diaminocyclohexane as the N-phthaloyl, N-tetrachlorophthaloyl or N-1,8-naphthaloyl derivative is presented. The first two derivatives are obtained with high yields and can be readily transformed into other unsymmetrical derivatives of trans-1,2-diaminocyclohexane.

An efficient method for the preparation of N,N-disubstituted 1,2-diamines

C2-Symmetric 1,2-diamines are useful precursors to numerous reagents used in asymmetric synthesis and catalysis. We report here an efficient protocol for converting the two most commonly used trans-1,2-diamines to N,N-disubstituted derivatives, a transformation that simplifies the preparation of non-C2-symmetric diamines. Central to the method is the high-yielding conversion of the diamines to the corresponding monoacetylated derivatives via imidazoline intermediates. (C) 2000 Published by Elsevier Science Ltd.