445479-92-5

Basic information

• Product Name: 1-(N-BENZYLOXYCARBONYL)-CIS-CYCLOHEXANE-1,2-DIAMINE
• Synonyms: 1-(N-BENZYLOXYCARBONYL)-CIS-CYCLOHEXANE-1,2-DIAMINE;1-(N-BENZYLOXYCARBONYL)-CIS-CYCLOHEXANE-1,2-DIAMINE (RACEMIC);cis-benzyl-2-aMinocyclohexylcarbaMate;Benzyl (cis-2-aMinocyclohexyl)carbaMate;CIS-1-AMINO-2-(CBZ-AMINO)-CYCLOHEXANE
• CAS NO: 445479-92-5
• Molecular Formula: C14H20N2O2
• Molecular Weight: 248.32
• Mol File: 445479-92-5.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-(N-BENZYLOXYCARBONYL)-CIS-CYCLOHEXANE-1,2-DIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(N-BENZYLOXYCARBONYL)-CIS-CYCLOHEXANE-1,2-DIAMINE(445479-92-5)
• EPA Substance Registry System: 1-(N-BENZYLOXYCARBONYL)-CIS-CYCLOHEXANE-1,2-DIAMINE(445479-92-5)

Safety Data

• Hazardous Substances Data: 445479-92-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(N-Benzyloxycarbonyl)-cis-cyclohexane-1,2-diamine is used as an intermediate in the synthesis of various pharmaceutical compounds for its ability to contribute to the development of new drugs and medications.
Used in Catalyst and Ligand Production:
In the field of catalysis, 1-(N-Benzyloxycarbonyl)-cis-cyclohexane-1,2-diamine is used as a component in the production of chiral catalysts and ligands, which are essential for enantioselective reactions and the synthesis of enantiomerically pure compounds.
Used in Medicinal Chemistry and Drug Development:
1-(N-BENZYLOXYCARBONYL)-CIS-CYCLOHEXANE-1,2-DIAMINE is utilized as a versatile building block in medicinal chemistry and drug development, enabling the creation of complex molecules and diverse chemical structures that can lead to the discovery of novel therapeutic agents.
Used in Advanced Materials and Organic Compounds Preparation:
1-(N-Benzyloxycarbonyl)-cis-cyclohexane-1,2-diamine is also used in the preparation of advanced materials and organic compounds, where its unique structure and properties contribute to the development of innovative products and technologies.

Upstream product

• 1257216-04-8 (3aR,7aR)-1,3,3a,4,5,6,7,7a-octahydrobenzimidazol-2-one 
• 100-51-6 benzyl alcohol 
• 28170-07-2 benzyl phenyl carbonate 
• 20439-47-8 (1R,2R)-1,2-diaminocyclohexane 
• 21436-03-3 (S,S)-1,2-diaminocyclohexane 
• 501-53-1 benzyl chloroformate 
• 180683-64-1 tert-butyl ((1S,2S)-2-aminocyclohexyl)carbamate 
• 957060-24-1 (1S,2R)-2-phthalimidocyclohexanecarboxylic acid 
• 957060-26-3 C₁₅H₁₄N₄O₃ 
• 383905-51-9 2-((R)-1-Phenyl-ethylamino)-cyclohex-1-enecarboxylic acid benzyl ester 
• 1436-59-5 cis-cyclohexane-1,2-diamine 
• 2205-32-5 benzyl 2-oxocyclohexanecarboxylate 
• 957060-27-4 (1S,2R)-1-(N-benzyloxycarbonylamino)-2-phthalimidocyclohexane 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 

Relevant articles and documents

DNA-cleavage activity of the iron(II) complex with optically active ligands, meta- and para-xylyl-linked N’,N’-dipyridylmethyl-cyclohexane-1,2-diamine

DNA-cleavage agents such as bleomycin have potential anticancer applications. The development of a DNA-cleavage reagent that recognizes specific sequences allows the development of cancer therapy with reduced side effects. In this study, to develop novel compounds with specific DNA-cleavage activities, we synthesized optically active binuclear ligands, (1R,1′R,2R,2′R)-N1,N1′-(meta/para-phenylenebis(methylene))bis(N2,N2-bis(pyridin-2-ylmethyl)cyclohexane-1,2-diamine) and their enantiomers. The DNA-cleavage activities of these compounds were investigated in the presence of Fe(II)SO4 and sodium ascorbate. The obtained results indicated that the Fe(II) complexes of those compounds efficiently cleave DNA and that their cleavage was subtle sequence-selective. Therefore, we succeeded in developing compounds that can be used as small-molecule drugs for cancer chemotherapy.

Design and synthesis of an anthranyl bridged optically active dinuclear iron(II)-ligand and evaluation of DNA-cleaving activity

It is necessary to design a ligand that is compatible with the target molecule to optimally use the DNA-cleaving ability of metal complexes. In this study, we synthesized an optically active dinuclear ligand, (1R,1′R,2R,2′R)-N1,N1′-(anthracene-1,8-diylbis(methylene))bis(N2,N2-bis(pyridin-2-ylmethyl)cyclohexane-1,2-diamine) (R-ABDC, 4a) and its enantiomer (S-ABDC, 4b). We then prepared their Fe(II) complexes by mixing the ligand with FeSO4·7H2O in situ and investigated DNA-cleaving activities using plasmid DNA in the presence of excess sodium ascorbate at atmospheric conditions. The Fe(II) complexes efficiently cleaved DNA and selectively recognized two consecutive A and/or T sequences.

Carbamate-based P,O-ligands for asymmetric allylic alkylations

Herein we report the design and successful catalytic application of modified Trost-ligands in asymmetric allylic alkylation (AAA) reactions. A small set of carbamate-monophosphine P,O-ligands has been prepared in a straightforward two-step synthetic procedure. After optimization of the reaction conditions, high catalytic activities and excellent enantioselectivity up to >99% have been attained.

Solvent-induced reversal of enantioselectivity in the synthesis of succinimides by the addition of aldehydes to maleimides catalysed by carbamate-monoprotected 1,2-diamines

A simple change in the polarity of the solvent allows both enantiomers of substituted succinimides to be obtained in the enantioselective conjugate addition reaction of aldehydes, mainly disubstituted, to maleimides catalysed by chiral carbamate-monoprote

Chiral primary amine tagged to ionic group as reusable organocatalyst for asymmetric Michael reactions of C-nucleophiles with α,β-unsaturated ketones

The first primary amine-derived organocatalyst modified with an ionic group for asymmetric Michael reactions of C-nucleophiles with α,β- unsaturated ketones was synthesized. In the presence of this catalyst and an acidic co-catalyst (AcOH), hydroxycoumarin and its sulfur-containing analogue reacted with benzylideneacetone derivatives or cyclohexenone to afford the corresponding Michael adducts in high yields (up to 97%) and with reasonable enantioselectivity (up to 80%). The catalyst could be easily recovered and efficiently reused three times, afterwards, its activity and stereodifferentiating ability gradually declined. The analysis of recovered catalyst samples by ESI-MS allowed us to detect undesirable side reactions that poisoned the catalyst, and propose an approach for its reactivation. Copyright

Synthesis of monoacylated derivatives of 1,2- cyclohexanediamine. Evaluation of their catalytic activity in the preparation of Wieland-Miescher ketone

Ureas, carbamoyl derivatives, amides, and sulfonamides can be easily prepared from the strained (R,R)-cylohexanediamine urea (1) in high yield, leaving a free amino group that shows good catalytic activity in intramolecular aldol condensations. The preparation of Wieland-Miescher ketone has been studied with these catalysts.

Design, synthesis, and biological evaluation of pirenzepine analogs bearing a 1,2-cyclohexanediamine and perhydroquinoxaline units in exchange for the piperazine ring as antimuscarinics

Pirenzepine (2) is one of the most selective muscarinic M1 versus M2 receptor antagonists known. A series of 2 analogs, in which the piperazyl moiety was replaced by a cis- and trans-cyclohexane-1,2-diamine (3-6) or a trans- and cis-

A novel bifunctional sulfonamide primary amine-catalyzed enantioselective conjugate addition of ketones to nitroolefins

The enantioselective conjugate addition of a variety of ketones to nitroolefins has been developed. The process is efficiently catalyzed by a novel bifunctional sulfonamide primary amine in good yields and with good levels of enantioselectivity.

A practical synthesis of enantiopure N-carbobenzyloxy-N′-phthaloyl-cis-1,2-cyclohexanediamine by asymmetric reductive amination and the Curtius rearrangement

Enantiomerically pure N-carbobenzyloxy-N′-phthaloyl-cis-1,2-cyclohexanediamine was synthesized by the asymmetric reduction of a β-enamino ester formed from benzyl 2-oxocyclohexanecarboxylate and (R)-phenylethylamine, followed by hydrogenolysis, phthaloyla

2,4-diamino-pyrimidines as aurora inhibitors

The present invention encompasses compounds of general formula (1) wherein R1 to R3 are defined as in claim 1, which are suitable for the treatment of diseases characterised by excessive or abnormal cell proliferation, and the use thereof for preparing a pharmaceutical composition having the above-mentioned properties.