142350-85-4

Basic information

• Product Name: 1-(N-BENZYLOXYCARBONYL)-TRANS-CYCLOHEXANE-1,2-DIAMINE
• Synonyms: 1-(N-BENZYLOXYCARBONYL)-TRANS-CYCLOHEXANE-1,2-DIAMINE;1-(N-BENZYLOXYCARBONYL)-TRANS-CYCLOHEXANE-1,2-DIAMINE (RACEMIC);(1R,2S)-Benzyl 1,2-diaMinocyclohexanecarboxylate;Benzyl (1R,2R)-2-AMinocyclohexylcarbaMate;Trans (1R,2R)-1N-Cbz-cyclohexane-1,2-diaMine;N-Cbz-(1R,2R)-(-)-Diaminocyclohexane
• CAS NO: 142350-85-4
• Molecular Formula: C₁₄H₂₀N₂O₂
• Molecular Weight: 248.32
• Mol File: 142350-85-4.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-(N-BENZYLOXYCARBONYL)-TRANS-CYCLOHEXANE-1,2-DIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(N-BENZYLOXYCARBONYL)-TRANS-CYCLOHEXANE-1,2-DIAMINE(142350-85-4)
• EPA Substance Registry System: 1-(N-BENZYLOXYCARBONYL)-TRANS-CYCLOHEXANE-1,2-DIAMINE(142350-85-4)

Safety Data

• Hazardous Substances Data: 142350-85-4(Hazardous Substances Data)

Usage

Description

1-(N-BENZYLOXYCARBONYL)-TRANS-CYCLOHEXANE-1,2-DIAMINE, also known as N-Cbz-(1R,2R)-(-)-Diaminocyclohexane, is an organic compound with a unique chemical structure that features a cyclohexane ring with two amine groups and a benzyloxycarbonyl (Cbz) protecting group. 1-(N-BENZYLOXYCARBONYL)-TRANS-CYCLOHEXANE-1,2-DIAMINE is known for its role in the synthesis of various pharmaceutical agents and has potential applications in the development of new drugs.

Uses

Used in Pharmaceutical Industry:
1-(N-BENZYLOXYCARBONYL)-TRANS-CYCLOHEXANE-1,2-DIAMINE is used as a reagent for the synthesis of anti-cancer agents, specifically AA005 derivatives. It plays a crucial role in the development of these drugs, which target cancer cells and help in their destruction.
1-(N-BENZYLOXYCARBONYL)-TRANS-CYCLOHEXANE-1,2-DIAMINE is also used in the preparation of pirenzepine analogs, which are known for their antimuscarinic properties. These analogs have potential applications in the treatment of various conditions, such as gastrointestinal disorders and urinary incontinence, by blocking the action of acetylcholine on muscarinic receptors.

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 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 142350-86-5 N-(R,R)-trans-2-benzyloxycarbonylaminocyclohexyl-N-tert-butyloxycarbonyl-p-nitrophenylalaninamide 
• 199336-08-8 {(1R,2R)-2-[(R)-2-tert-Butoxycarbonylamino-3-(4-nitro-phenyl)-propionylamino]-cyclohexyl}-carbamic acid benzyl ester 
• 133725-77-6 N-<(S)-2-amino-3-(p-nitrophenyl)propyl>-trans-(R,R)-cyclohexane-1,2-diamine-N,N',N'N'',N''-penta-acetic acid 
• 1001601-38-2 C₂₈H₄₆N₂O₅ 
• 1155956-53-8 benzyl (1R,2R)-2-((E)-2-hydroxybenzylideneamino)cyclohexylcarbamate 
• 1438415-80-5 3-(5-((1R,2R)-2-aminocyclohexylamino)-5-oxopentyl)-1-methyl-1H-imidazol-3-iumhexafluorophosphate 
• 1438415-82-7 1-(5-((1R,2R)-2-(benzyloxycarbonylamino)cyclohexylamino)-5-oxopentyl)-3-methyl-1H-imidazol-3-ium bromide 
• 1438415-84-9 1-(5-((1R,2R)-2-(benzyloxycarbonylamino)cyclohexylamino)-5-oxopentyl)-3-methyl-1H-imidazol-3-ium hexafluorophosphate 
• 1438415-81-6 benzyl (1R,2R)-2-(5-bromopentanamido)cyclohexylcarbamate 

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.

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.