Cas no 149423-77-8 (trans-4-(Benzyloxycarbonylamino)cyclohexylamine)

Technical Introduction: trans-4-(Benzyloxycarbonylamino)cyclohexylamine is a chiral cyclohexylamine derivative featuring a benzyloxycarbonyl (Cbz) protecting group on the amine functionality. This compound is valuable in organic synthesis and pharmaceutical research, particularly for peptide coupling and as a building block in the preparation of stereochemically defined intermediates. The trans-configuration ensures consistent spatial orientation, enhancing selectivity in reactions. The Cbz group offers reversible protection, facilitating deprotection under mild conditions while maintaining stability during synthetic transformations. Its rigid cyclohexyl backbone contributes to conformational control, making it useful in designing bioactive molecules. Suitable for applications requiring controlled amine reactivity and stereochemical precision.
trans-4-(Benzyloxycarbonylamino)cyclohexylamine structure
149423-77-8 structure
Product Name:trans-4-(Benzyloxycarbonylamino)cyclohexylamine
CAS No:149423-77-8
MF:C14H20N2O2
MW:248.320803642273
MDL:MFCD03839901
CID:100236
Update Time:2025-10-29

trans-4-(Benzyloxycarbonylamino)cyclohexylamine Chemical and Physical Properties

Names and Identifiers

    • Benzyl (trans-4-aminocyclohexyl)carbamate
    • 1-N-CBZ-TRANS-1,4-CYCLOHEXYLDIAMINE
    • Benzyl trans-4-aminocyclohexylcarbamate
    • Carbamic acid,N-(trans-4-aminocyclohexyl)-, phenylmethyl ester
    • N-Cbz-trans-1,4-cyclohexanediamine
    • 4-cyclohexanediaMine
    • benzyl (1r,4r)-4-aMinocyclohexylcarbaMate
    • N-Cbz-trans-1
    • N-Cbz-trans-1,4-cyclohexanediaminehydrochloride
    • TRANS-(4-AMINO-CYCLOHEXYL)-CARBAMIC ACID BENZYL ESTER
    • trans-N-Cbz-4-aminocyclohexylamine
    • Cis-1N-Cbz-cyclohexane-1,4-diaMine
    • trans-Benzyl (4-aminocyclohexyl) carbamate
    • trans-4-(Benzyloxycarbonylamino)cyclohexylamine
    • MDL: MFCD03839901
    • Inchi: 1S/C14H20N2O2/c15-12-6-8-13(9-7-12)16-14(17)18-10-11-4-2-1-3-5-11/h1-5,12-13H,6-10,15H2,(H,16,17)
    • InChI Key: JQVBZZUMWRXDSQ-UHFFFAOYSA-N
    • SMILES: O(CC1C=CC=CC=1)C(NC1CCC(CC1)N)=O

Computed Properties

  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 18
  • Rotatable Bond Count: 5

Experimental Properties

  • Color/Form: Pale-yellow to Yellow-brown Solid
  • Water Partition Coefficient: Slightly soluble in water.

trans-4-(Benzyloxycarbonylamino)cyclohexylamine Security Information

trans-4-(Benzyloxycarbonylamino)cyclohexylamine Pricemore >>

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Additional information on trans-4-(Benzyloxycarbonylamino)cyclohexylamine

Professional Introduction to trans-4-(Benzyloxycarbonylamino)cyclohexylamine (CAS No. 149423-77-8)

trans-4-(Benzyloxycarbonylamino)cyclohexylamine, with the CAS number 149423-77-8, is a specialized organic compound that has garnered significant attention in the field of pharmaceutical research and development. This compound belongs to the class of amino acid derivatives, characterized by its unique structural and functional properties. The presence of a benzyloxycarbonyl (Boc) group and a cyclohexylamine moiety imparts distinct reactivity and stability, making it a valuable intermediate in the synthesis of various bioactive molecules.

The benzyloxycarbonyl group is a well-known protecting group in peptide chemistry, widely employed to prevent the deprotection of amino groups during synthetic procedures. This feature makes trans-4-(Benzyloxycarbonylamino)cyclohexylamine particularly useful in the construction of peptide mimetics and other peptidomimetic drugs. The cyclohexylamine portion contributes to the compound's solubility and bioavailability, which are critical factors in drug design and formulation.

In recent years, there has been a surge in research focused on developing novel therapeutic agents that target neurological disorders, such as Alzheimer's disease and Parkinson's disease. The cyclohexylamine backbone is known to enhance the blood-brain barrier penetration of drugs, a property that has been leveraged in the design of neuroprotective agents. Furthermore, the Boc-protected amino group allows for selective modification during synthetic pathways, enabling researchers to fine-tune the pharmacological properties of their target molecules.

One of the most compelling applications of trans-4-(Benzyloxycarbonylamino)cyclohexylamine is in the field of enzyme inhibition. The compound's structural framework is conducive to binding with various enzymatic targets, making it a promising scaffold for developing inhibitors of therapeutic interest. For instance, studies have demonstrated its potential in inhibiting enzymes involved in inflammation and pain signaling pathways. These findings have opened up new avenues for the development of anti-inflammatory and analgesic drugs.

The synthesis of trans-4-(Benzyloxycarbonylamino)cyclohexylamine involves multi-step organic reactions that require precise control over reaction conditions. The use of advanced catalytic systems and green chemistry principles has enabled more efficient and environmentally friendly synthetic routes. These advancements not only improve yield but also reduce waste, aligning with the growing emphasis on sustainable chemical practices.

Recent breakthroughs in computational chemistry have further enhanced the utility of trans-4-(Benzyloxycarbonylamino)cyclohexylamine. Molecular modeling studies have provided insights into its interaction with biological targets at an atomic level, facilitating the rational design of more effective drug candidates. These computational approaches are complemented by experimental validation, ensuring that the synthesized compounds exhibit the desired pharmacological properties.

The role of trans-4-(Benzyloxycarbonylamino)cyclohexylamine in drug discovery extends beyond its use as an intermediate. It has also been explored as a building block for designing novel molecular entities with unique pharmacokinetic profiles. For example, modifications to its structure have led to compounds with improved metabolic stability and reduced toxicity, key factors in successful drug development.

In conclusion, trans-4-(Benzyloxycarbonylamino)cyclohexylamine (CAS No. 149423-77-8) represents a significant advancement in pharmaceutical chemistry. Its unique structural features and versatile reactivity make it an indispensable tool in the synthesis of bioactive molecules targeting various diseases. As research continues to uncover new applications for this compound, its importance in drug development is set to grow even further.

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