Cas no 889858-07-5 (benzyl N-(1R)-1-cyanopropylcarbamate)

Benzyl N-(1R)-1-cyanopropylcarbamate is a chiral carbamate derivative featuring a cyanopropyl group, which enhances its utility in asymmetric synthesis and pharmaceutical intermediates. The (1R)-stereochemistry ensures high enantioselectivity, making it valuable for applications requiring precise chiral control. Its benzyloxycarbonyl (Cbz) protecting group offers stability under various reaction conditions while remaining selectively removable. The nitrile functionality provides additional reactivity for further derivatization. This compound is particularly useful in peptide synthesis and medicinal chemistry, where its structural features contribute to efficient coupling and functional group transformations. Its well-defined stereochemistry and synthetic versatility make it a reliable choice for research and industrial applications.
benzyl N-(1R)-1-cyanopropylcarbamate structure
889858-07-5 structure
Product Name:benzyl N-(1R)-1-cyanopropylcarbamate
CAS No:889858-07-5
MF:C12H14N2O2
MW:218.251762866974
CID:1935938
PubChem ID:66935237
Update Time:2025-11-01

benzyl N-(1R)-1-cyanopropylcarbamate Chemical and Physical Properties

Names and Identifiers

    • Carbamic acid, [(1R)-1-cyanopropyl]-, phenylmethyl ester
    • benzyl N-(1R)-1-cyanopropylcarbamate
    • SCHEMBL1186365
    • 889858-07-5
    • N-benzyloxycarbonyl-(1R)-1-cyanopropylamine
    • EN300-10837213
    • TWAWFUGNYJFAEX-LLVKDONJSA-N
    • benzyl N-[(1R)-1-cyanopropyl]carbamate
    • Inchi: 1S/C12H14N2O2/c1-2-11(8-13)14-12(15)16-9-10-6-4-3-5-7-10/h3-7,11H,2,9H2,1H3,(H,14,15)/t11-/m1/s1
    • InChI Key: TWAWFUGNYJFAEX-LLVKDONJSA-N
    • SMILES: O(C(N[C@@H](C#N)CC)=O)CC1C=CC=CC=1

Computed Properties

  • Exact Mass: 218.105527694Da
  • Monoisotopic Mass: 218.105527694Da
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 5
  • Complexity: 263
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2.2
  • Topological Polar Surface Area: 62.1?2

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Additional information on benzyl N-(1R)-1-cyanopropylcarbamate

Benzyl N-(1R)-1-Cyanopropylcarbamate: A Comprehensive Overview

Benzyl N-(1R)-1-cyanopropylcarbamate (CAS No. 889858-07-5) is a compound of significant interest in the field of organic chemistry and pharmaceutical research. This compound, with its unique structure and properties, has garnered attention for its potential applications in drug development and advanced material synthesis. In this article, we will delve into the structural characteristics, synthesis methods, biological activities, and recent advancements associated with benzyl N-(1R)-1-cyanopropylcarbamate.

The molecular structure of benzyl N-(1R)-1-cyanopropylcarbamate is defined by its chiral center at the propyl group, which imparts stereochemical properties to the molecule. The presence of a cyan group (-CN) and a carbamate functional group (-O-CO-N-) makes this compound versatile in terms of reactivity and functionality. Recent studies have highlighted the importance of stereochemistry in determining the biological activity of such compounds, making benzyl N-(1R)-1-cyanopropylcarbamate a valuable model for exploring enantioselective reactions and asymmetric catalysis.

One of the most notable aspects of benzyl N-(1R)-1-cyanopropylcarbamate is its role as an intermediate in the synthesis of bioactive molecules. Researchers have utilized this compound to construct complex structures with potential therapeutic applications. For instance, its ability to undergo nucleophilic substitution reactions has been exploited in the development of novel antibiotics and antiviral agents. The latest findings in this area suggest that benzyl N-(1R)-1-cyanopropylcarbamate could serve as a precursor for drugs targeting specific enzyme pathways involved in bacterial resistance mechanisms.

In terms of synthesis, benzyl N-(1R)-1-cyanopropylcarbamate can be prepared via several routes, including nucleophilic acylation and reductive amination. Recent advancements in catalytic asymmetric synthesis have enabled the efficient production of this compound with high enantiomeric excess (ee). These methods not only enhance the yield but also reduce the environmental footprint, aligning with current trends toward sustainable chemical processes.

The biological activity of benzyl N-(1R)-1-cyanopropylcarbamate has been extensively studied, particularly in relation to its potential as a chiral auxiliary in organic synthesis. Experimental data indicate that this compound exhibits moderate inhibitory effects on certain proteases, making it a candidate for further exploration in enzyme inhibition studies. Additionally, its role as a building block in peptide synthesis has been documented, showcasing its versatility in medicinal chemistry.

From an environmental perspective, understanding the fate and toxicity of benzyl N-(1R)-1-cyanopropylcarbamate is crucial for its safe handling and application. Recent toxicological studies have demonstrated that this compound exhibits low acute toxicity under standard test conditions. However, further research is needed to evaluate its long-term effects and potential bioaccumulation in aquatic systems.

In conclusion, benzyl N-(1R)-1-cyanopropylcarbamate (CAS No. 889858-07-5) stands out as a multifaceted compound with promising applications across various domains of chemistry and biology. Its unique structure, coupled with advancements in synthetic methodologies and biological studies, positions it as a key player in future research endeavors. As ongoing investigations continue to uncover new insights into its properties and uses, benzyl N-(1R)-1-cyanopropylcarbamate is poised to make significant contributions to the development of innovative chemical solutions.

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