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
• Article Data: 13

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

Description

1-(N-Benzyloxycarbonyl)-cis-cyclohexane-1,2-diamine is a chemical compound that serves as an intermediate in the preparation of various pharmaceutical compounds. It is also used in the production of chiral catalysts and ligands. This versatile building block is crucial in the creation of complex molecules and the construction of diverse chemical structures. It plays a significant role in medicinal chemistry, drug development, and the preparation of advanced materials and organic compounds.

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

• 20439-47-8 (1R,2R)-1,2-diaminocyclohexane 
• 501-53-1 benzyl chloroformate 
• 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 
• 21436-03-3 (S,S)-1,2-diaminocyclohexane 
• 180683-64-1 tert-butyl ((1S,2S)-2-aminocyclohexyl)carbamate 
• 957060-27-4 (1S,2R)-1-(N-benzyloxycarbonylamino)-2-phthalimidocyclohexane 
• 957060-24-1 (1S,2R)-2-phthalimidocyclohexanecarboxylic acid 
• 957060-26-3 C₁₅H₁₄N₄O₃ 
• 2205-32-5 benzyl 2-oxocyclohexanecarboxylate 
• 189101-41-5 (1S,2R)-(+)-2-aminocyclohexane-1-carboxylic acid 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 
• 383905-51-9 2-((R)-1-Phenyl-ethylamino)-cyclohex-1-enecarboxylic acid benzyl ester 

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.

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.

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