191480-61-2

Usage

Uses

Used in Organic Synthesis:
1S,2S-N,N'-bis(phenylMethyl)-1,2-CyclohexanediaMine is used as a chiral ligand for facilitating asymmetric synthesis reactions. Its unique structure allows for the selective formation of enantiomerically pure compounds, which is crucial in the production of pharmaceuticals and agrochemicals where stereochemistry plays a significant role in biological activity.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1S,2S-N,N'-bis(phenylMethyl)-1,2-CyclohexanediaMine is utilized as a chiral building block for the development of new drugs. Its ability to induce selectivity in chemical reactions can lead to the creation of more effective and safer medications with fewer side effects.
Used in Materials Science:
1S,2S-N,N'-bis(phenylMethyl)-1,2-CyclohexanediaMine is employed in materials science for the design and synthesis of novel chiral materials. These materials have potential applications in various fields, including sensors, catalysts, and optoelectronic devices, where chirality can impart unique properties.
Used as an Anti-inflammatory Agent:
1S,2S-N,N'-bis(phenylMethyl)-1,2-CyclohexanediaMine has been found to exhibit anti-inflammatory properties, making it a potential candidate for the development of new treatments for inflammatory diseases such as arthritis, asthma, and inflammatory bowel disease.
Used as an Anti-cancer Agent:
1S,2S-N,N'-bis(phenylMethyl)-1,2-CyclohexanediaMine has demonstrated biological activity as an anti-cancer agent, suggesting its potential use in the development of new cancer therapies. Further research is needed to explore its mechanism of action and efficacy in treating various types of cancer.

Upstream product

• 65838-45-1 N,N'-(cyclohexane-1,2-diyl)bis(1-phenylmethanimine) 
• 3187-82-4 (±)-trans-N,N′-1,2-cyclohexylenebis(benzylideneamine) 
• 24417-01-4 7-Benzyl-7-aza-bicyclo[4.1.0]heptane 
• 100-46-9 benzylamine 
• 286-20-4 cyclohexane-1,2-epoxide 
• 100-52-7 benzaldehyde 
• 1121-22-8 trans-1,2-Diaminocyclohexane 
• 32044-22-7 (R,R)-1,2-diaminocyclohexane*(+)-tartric acid 
• 100-44-7 benzyl chloride 
• 32044-22-7 (1R,2R)-1,2-diaminocyclohexane tartrate 
• 20439-47-8 (1R,2R)-1,2-diaminocyclohexane 
• 57707-55-8 (1R,2R)-N¹,N²-dibenzoyl-1,2-diaminocyclohexane 
• 199180-98-8 (1R,2R)-N,N'-dibenzylidene-1,2-diaminocyclohexane 
• 100-39-0 benzyl bromide 

Downstream Products

• 1372610-45-1 (1R,2R)-N,N'-dibenzyl-N,N'-bis(ethan-(1-(S)-methyl)-1-ol)-trans-diaminocyclohexane 
• 65838-10-0 (1R,2R)-N,N'-dibenzylcyclohexane-1,2-diamine 
• 1446520-81-5 1,3-dibenzyl perhydrobenzimidazolinium chloride 
• 135613-99-9 (R,S)-(3al,7al,1'lu)-1,3-dibenzyloctahydro-2-(4'-methyl-1',2'-pentadienyl)-1H-1,3,2-benzodiazaphosphole 2-oxide 
• 135614-00-5 (R,S)-(3al,7al,1'lu)-1,3-dibenzyloctahydro-2-(4',4'-dimethyl-1',2'-pentadienyl)-1H-1,3,2-benzodiazaphosphole 2-oxide 
• 135613-97-7 (R,S)-(3al,7al,1'lu)-1,3-dibenzyl-2-(1',2'-butadienyl)-octahydro-1H-1,3,2-benzodiazaphosphole 2-oxide 
• 135613-98-8 (R,S)-(3al,7al)-1,3-dibenzyloctahydro-2-(3'-methyl-1',2'-butadienyl)-1H-1,3,2-benzodiazaphosphole 2-oxide 
• 1430069-04-7 C₄₄H₅₆N₄O₂P₂ 
• 1429938-87-3 C₄₄H₅₆N₄O₂P₂ 
• 1430069-15-0 C₄₄H₅₆N₄O₂P₂Se₂ 
• 1429938-89-5 C₄₆H₅₈N₄O₂P₂ 
• 1429939-23-0 C₄₄H₅₆N₄O₂P₂Se₂ 

Relevant academic research and scientific papers

Machine-Assisted Preparation of a Chiral Diamine Ligand Library and In Silico Screening Using Ab Initio Structural Parameters for Heterogeneous Chiral Catalysts

A ligand library containing 31 chiral diamines was synthesized using a flow-based semiautomatic reductive amination system. These ligands were evaluated in a continuous-flow asymmetric 1,4-addition reaction with a heterogeneous Ni catalyst. Based on the experimental results of ab initio DFT calculations, a prediction model for enantioselectivities was successfully constructed. Furthermore, virtual screening of possible ligands was conducted to identify promising structures, which showed good enantioselectivities in experiments. (Figure presented.).

Nickel-Catalyzed Asymmetric C-Alkylation of Nitroalkanes: Synthesis of Enantioenriched β-Nitroamides

A general catalytic method for asymmetric C-alkylation of nitroalkanes using nickel catalysis is described. This method enables the formation of highly enantioenriched β-nitroamides from readily available α-bromoamides using mild reaction conditions that are compatible with a wide range of functional groups. When combined with subsequent reactions, this method allows access to highly enantioenriched products with nitrogen-bearing fully substituted carbon centers.

METAL CHELATORS FOR IMAGING, THERAPEUTICS, AND BIOANALYSIS

A variety of compounds are provided capable of chelating a metal, in particular a lanthanide such as Eu(III) and Tb(III). Luminescent complexes of the compound and a metal ion are also provided, in particular luminescent metal complexes are provided containing a lanthanide such as Eu(III) or Tb(III) and a compound described herein. In some aspects, the luminescent complexes are capable of exhibiting bright emissions with high quantum yields. Methods of making the compound are provided. Methods of using the compounds and luminescent complexes are also provided, for example for imaging and therapeutic applications.

Nitroalkenes in the Ni(II) Catalyzed Asymmetric Michael Addition. Convenient Route to the Key Intermediate of Brivaracetam

A series of Ni(II) complexes with novel chiral ligands derived from (1R,2R)-1,2-diphenylethane-1,2-diamine was synthesized. The catalytic activity of these complexes in the asymmetric Michael reaction is demonstrated. Asymmetric addition of diethyl malonate to ω-nitrostyrene and 1-nitropent-1-ene in the presence of these complexes leads to the enantiomerically enriched diethyl (S)-2-(2-nitro-1-phenylethyl)malonate (up to 96 % ee) and (R)-diethyl 2-(1-nitropenthan-2-yl)malonate (up to 91 % ee). (4R)-4-Propylpyrrolidin-2-one, the key intermediate of antiepileptic drug brivaracetam, was obtained from the corresponding nitroester.

Efficient route to pre-organized and linear polyaminopolycarboxylates: Cy-TTHA, Cy-DTPA and mono/di- reactive, tert-butyl protected TTHA/Cy-TTHA

Pre-organized polyaminopolycarboxylate chelators Cy-TTHA and Cy-DTPA were synthesized via modular five-step syntheses from commercially available starting materials in ～62% and 47% overall yields, respectively. Furthermore, strategies are reported for the efficient preparation of mono- and di-reactive, tert-butyl-protected TTHA/Cy-TTHA to selectively functionalize central chelators’ carboxylic acids.

Synthesis and crystal structure of a chiral lactam and three amino alcohols as potential protein tyrosine phosphates 1B inhibitors

Chiral lactam 2 and three chiral β-amino alcohols 3–5 have been synthesized and characterized by spectroscopic techniques. Regioselective ring opening reaction of chiral styrene oxide by an amine nucleophile was confirmed by X-ray diffraction data. Ligand 2–4 crystallizes in the tetragonal, orthorhombic and tetragonal crystal lattice system respectively. Ligands 2–6 have been used as potential inhibitors for protein tyrosine phosphatase 1B enzyme (PTP1B). The potential inhibitor effect of these molecules to the target protein was investigated by Dock and molecular dynamics calculations. Dock score analysis and Lipinski parameters suggested that ligands 1, 2, 4–6 are potential inhibitors towards PTP1B, thus indicating that the residues Arg24, Arg254 and Met258, Asp29 in the second active site of PTP1B are essential for the high selectivity of inhibitors. The results indicate that the polar hydrogen bonding interacts with Asp29, Gln102, and the amino acid residues of PTP1B are responsible for governing inhibitory potency of ligands 1–6.

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.

Gas-Solid Chemisorption/Adsorption and Mechanochemical Selectivity in Dynamic Nonporous Hybrid Metal Organic Materials

Gas-solid chemisorption of HCl and adsorption of MeOH/EtOH by nonporous chiral copper(II) coordination complexes 1·MeOH and 1·MeOH occur in a cooperative and dynamic manner to give solvated second sphere adducts 1′·MeOH/EtOH. The chemisorption process involves dramatic atomic rearrangements in the crystalline state upon cleavage and formation of H-Cl, N-H, Cu-N, and Cu-Cl coordination and covalent bonds from the gas and solid state, respectively. Using mechanochemistry, the chloride-bridged coordination complex 1·MeOH is selectively produced by means of a dehydrochlorination reaction, but not in solution in which a mixture of 1·MeOH and 1·MeOH is obtained. 1·MeOH also via chemisorption and adsorption can trap HCl and MeOH to give the second sphere adduct 1′·MeOH. The adsorption process is confirmed by forming the second sphere adduct 1′·EtOH by exposing both 1·MeOH and 1·MeOH to HCl and ethanol. Quantum-mechanical (QM) calculations specific for solid phases give insights into the relative stabilities of the hybrid metal organic materials involved in the mechanochemical reaction producing selectively 1·MeOH, giving a good agreement with the experimental results.

Mechanosynthesis of Second-Sphere Coordination Salts and Chelating Complexes: Structures, Reversible Transformations, and Nitroaromatic Explosives Sensing

We have investigated the mechanosynthesis of a series of second-sphere salts, guest?[H2L]2+·[MCl4]2– [L = N,N′-dibenzyl-(±)-trans-1,2-diaminocyclohexane], and the reversible transformations to their chelating coordination complexes [MCl2(L)] through dehydrochlorination reactions. The second-sphere salts and their corresponding coordination complexes show different solid-state fluorescence spectra. The complex ZnCl2(L) (2′) acts as a sensor for the highly sensitive detection of nitroaromatic compounds through fluorescence quenching.

Organocatalytic Knoevenagel condensation by chiral: C 2-symmetric tertiary diamines

The efficient Knoevenagel condensation catalyzed by (1S,2S)-1,2-diaminocyclohexane derivatives is presented and investigated. Various aliphatic aldehydes undergo condensation with active methylene compounds to yield the corresponding products in high yields. α-Branched aldehydes were found to be efficiently converted to the corresponding enantiomerically enriched products by using these chiral tertiary diamine catalysts.