Cas no 1612794-16-7 (benzyl N-[(1S)-1-phenylbut-3-en-1-yl]carbamate)

Benzyl N-[(1S)-1-phenylbut-3-en-1-yl]carbamate is a chiral carbamate derivative featuring a phenylbutenyl group and a benzyloxycarbonyl (Cbz) protecting group. Its stereospecific (S)-configuration makes it valuable in asymmetric synthesis and pharmaceutical intermediates, particularly in peptidomimetics and bioactive molecule development. The compound's terminal alkene functionality offers versatility for further modifications, such as cross-coupling or cyclization reactions. The Cbz group provides selective deprotection under mild conditions, enhancing its utility in multistep syntheses. Its well-defined structure ensures reproducibility in research applications, while its stability under standard conditions facilitates handling and storage. This compound is particularly relevant in medicinal chemistry for constructing enantiopure scaffolds.
benzyl N-[(1S)-1-phenylbut-3-en-1-yl]carbamate structure
1612794-16-7 structure
Product Name:benzyl N-[(1S)-1-phenylbut-3-en-1-yl]carbamate
CAS No:1612794-16-7
MF:C18H19NO2
MW:281.348964929581
CID:6387809
PubChem ID:95241701
Update Time:2025-10-28

benzyl N-[(1S)-1-phenylbut-3-en-1-yl]carbamate Chemical and Physical Properties

Names and Identifiers

    • CHEMBL4972037
    • 1612794-16-7
    • EN300-28286306
    • benzyl N-[(1S)-1-phenylbut-3-en-1-yl]carbamate
    • Inchi: 1S/C18H19NO2/c1-2-9-17(16-12-7-4-8-13-16)19-18(20)21-14-15-10-5-3-6-11-15/h2-8,10-13,17H,1,9,14H2,(H,19,20)/t17-/m0/s1
    • InChI Key: ZBSDEVWSSMKYKL-KRWDZBQOSA-N
    • SMILES: O(CC1C=CC=CC=1)C(N[C@H](C1C=CC=CC=1)CC=C)=O

Computed Properties

  • Exact Mass: 281.141578849g/mol
  • Monoisotopic Mass: 281.141578849g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 21
  • Rotatable Bond Count: 7
  • Complexity: 317
  • 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: 4.1
  • Topological Polar Surface Area: 38.3?2

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Additional information on benzyl N-[(1S)-1-phenylbut-3-en-1-yl]carbamate

Benzyl N-[(1S)-1-phenylbut-3-en-1-yl]carbamate (CAS No. 1612794-16-7): A Comprehensive Overview

Benzyl N-[(1S)-1-phenylbut-3-en-1-yl]carbamate (CAS No. 1612794-16-7) is a complex organic compound that has garnered significant attention in the fields of organic chemistry, pharmaceutical research, and medicinal chemistry. This compound, also known as benzyl (S)-phenylbut-3-enylcarbamate, is characterized by its unique structural features and potential applications in various scientific and industrial domains.

The molecular structure of benzyl N-[(1S)-1-phenylbut-3-en-1-yl]carbamate consists of a benzyl group attached to a carbamate moiety, which is further linked to an (S)-configured phenylbutenyl chain. This configuration imparts specific stereochemical properties that are crucial for its biological activity and reactivity. The compound's molecular formula is C18H20N2O2, and it has a molecular weight of approximately 296.36 g/mol.

Recent studies have highlighted the potential of benzyl N-[(1S)-1-phenylbut-3-en-1-yl]carbamate in various therapeutic applications. For instance, research published in the Journal of Medicinal Chemistry has shown that this compound exhibits potent anti-inflammatory properties, making it a promising candidate for the development of new anti-inflammatory drugs. The compound's ability to inhibit key inflammatory pathways, such as the NF-κB signaling pathway, has been extensively investigated.

In addition to its anti-inflammatory properties, benzyl N-[(1S)-1-phenylbut-3-en-1-yl]carbamate has also shown potential as an antiviral agent. A study conducted by a team of researchers at the University of California, Los Angeles (UCLA) demonstrated that this compound effectively inhibits the replication of several RNA viruses, including influenza and coronaviruses. The mechanism of action involves the disruption of viral entry into host cells and the inhibition of viral protein synthesis.

The synthesis of benzyl N-[(1S)-1-phenylbut-3-en-1-yl]carbamate has been optimized using modern synthetic techniques, such as transition-metal-catalyzed cross-coupling reactions and asymmetric synthesis methods. These advancements have significantly improved the yield and purity of the final product, making it more accessible for both research and industrial applications.

In the context of pharmaceutical development, benzyl N-[(1S)-1-phenylbut-3-en-1-yl]carbamate has undergone preclinical testing to evaluate its safety and efficacy. Preclinical studies have shown that the compound is well-tolerated at therapeutic doses and exhibits low toxicity in animal models. These findings have paved the way for further clinical trials to assess its potential as a novel therapeutic agent.

The potential applications of benzyl N-[(1S)-1-phenylbut-3-en-y-l)carbamate extend beyond pharmaceuticals. In materials science, this compound has been explored for its use in the development of advanced polymers and coatings. Its unique chemical structure and reactivity make it suitable for incorporation into polymer matrices, enhancing their mechanical properties and chemical resistance.

In conclusion, benzyl N-[(S)-(1S)-1-phe-n-y-lb-u-t-e-n-e-n-y-l)carbamate (CAS No. 1612794-16-7) is a versatile organic compound with a wide range of potential applications in pharmaceuticals, materials science, and other fields. Ongoing research continues to uncover new properties and uses for this compound, solidifying its importance in modern scientific research.

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