Cas no 65414-83-7 (Benzenepropanoic acid, b-[(2-phenylacetyl)amino]-, (bS)-)

Benzenepropanoic acid, β-[(2-phenylacetyl)amino]-, (βS)-, is a chiral organic compound characterized by its phenylacetyl-substituted propanoic acid structure with a stereocenter at the β-position. This compound is of interest in synthetic and medicinal chemistry due to its potential as a building block for peptidomimetics or bioactive molecules. The (βS)-configuration ensures enantioselectivity in reactions, making it valuable for asymmetric synthesis. Its aromatic and amide functionalities provide sites for further derivatization, enhancing versatility in drug discovery and material science applications. The compound's purity and defined stereochemistry are critical for reproducibility in research and industrial processes. Suitable for use under controlled conditions, it requires proper handling due to its reactive groups.
Benzenepropanoic acid, b-[(2-phenylacetyl)amino]-, (bS)- structure
65414-83-7 structure
Product Name:Benzenepropanoic acid, b-[(2-phenylacetyl)amino]-, (bS)-
CAS No:65414-83-7
MF:C17H17NO3
MW:283.321784734726
CID:501570
PubChem ID:818067
Update Time:2025-09-23

Benzenepropanoic acid, b-[(2-phenylacetyl)amino]-, (bS)- Chemical and Physical Properties

Names and Identifiers

    • Benzenepropanoic acid, b-[(2-phenylacetyl)amino]-, (bS)-
    • (3S)-3-phenyl-3-[(2-phenylacetyl)amino]propanoic acid
    • (S)-N-PHENYLACETYL-BETA-PHENYLALANINE
    • (S)-3-phenyl-3-(2-phenylacetamido)propanoic acid
    • (S)-3-PHENYL-3-PHENYLACETYLAMINO-PROPIONIC ACID
    • DTXSID30355898
    • 65414-83-7
    • Inchi: 1S/C17H17NO3/c19-16(11-13-7-3-1-4-8-13)18-15(12-17(20)21)14-9-5-2-6-10-14/h1-10,15H,11-12H2,(H,18,19)(H,20,21)/t15-/m0/s1
    • InChI Key: URKWJOAJRKPEFW-HNNXBMFYSA-N
    • SMILES: O=C(CC1C=CC=CC=1)N[C@@H](CC(=O)O)C1C=CC=CC=1

Computed Properties

  • Exact Mass: 283.12100
  • Monoisotopic Mass: 283.12084340g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 21
  • Rotatable Bond Count: 6
  • Complexity: 344
  • 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: 66.4?2

Experimental Properties

  • PSA: 66.40000
  • LogP: 2.95220

Benzenepropanoic acid, b-[(2-phenylacetyl)amino]-, (bS)- Customs Data

  • HS CODE:2924299090
  • Customs Data:

    China Customs Code:

    2924299090

    Overview:

    2924299090. Other cyclic amides(Including cyclic carbamates)(Including their derivatives as well as their salts). VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:30.0%

    Declaration elements:

    Product Name, component content, use to, packing

    Summary:

    2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Benzenepropanoic acid, b-[(2-phenylacetyl)amino]-, (bS)- Pricemore >>

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A019124620-5g
(S)-N-Phenylacetyl-beta-phenylalanine
65414-83-7 97%
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$1321.92 2023-09-01

Benzenepropanoic acid, b-[(2-phenylacetyl)amino]-, (bS)- Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Sodium bicarbonate Solvents: Water
Reference
An expedient synthesis of 6-arylpiperidine-2,4-diones by chain-extension of β-aryl-β-amino acids
Leflemme, Nicolas; et al, Tetrahedron Letters, 2001, 42(51), 8997-8999

Production Method 2

Reaction Conditions
1.1 Solvents: Acetone ,  Water
2.1 Reagents: Sodium bicarbonate Solvents: Water
Reference
An expedient synthesis of 6-arylpiperidine-2,4-diones by chain-extension of β-aryl-β-amino acids
Leflemme, Nicolas; et al, Tetrahedron Letters, 2001, 42(51), 8997-8999

Production Method 3

Reaction Conditions
1.1 Catalysts: Penicillin amidase (immobilized on Eupergit) Solvents: Ethanol ,  Water
Reference
A Stereoselective Synthesis of (2R,3S)-N-Benzoylphenylisoserine Methyl Ester
Cardillo, Giuliana; et al, Journal of Organic Chemistry, 1998, 63(7), 2351-2353

Production Method 4

Reaction Conditions
1.1 Reagents: Triethylamine Solvents: Acetone ,  Water
2.1 Catalysts: Penicillin amidase (immobilized on Eupergit) Solvents: Ethanol ,  Water
Reference
A Stereoselective Synthesis of (2R,3S)-N-Benzoylphenylisoserine Methyl Ester
Cardillo, Giuliana; et al, Journal of Organic Chemistry, 1998, 63(7), 2351-2353

Production Method 5

Reaction Conditions
1.1 Reagents: Ammonium acetate Solvents: Ethanol
2.1 Reagents: Triethylamine Solvents: Acetone ,  Water
3.1 Catalysts: Penicillin amidase (immobilized on Eupergit) Solvents: Ethanol ,  Water
Reference
A Stereoselective Synthesis of (2R,3S)-N-Benzoylphenylisoserine Methyl Ester
Cardillo, Giuliana; et al, Journal of Organic Chemistry, 1998, 63(7), 2351-2353

Benzenepropanoic acid, b-[(2-phenylacetyl)amino]-, (bS)- Raw materials

Benzenepropanoic acid, b-[(2-phenylacetyl)amino]-, (bS)- Preparation Products

Additional information on Benzenepropanoic acid, b-[(2-phenylacetyl)amino]-, (bS)-

Benzenepropanoic Acid, B-[(2-Phenylacetyl)Amino]-, (B-S)-: A Comprehensive Overview

Benzenepropanoic acid, b-[(2-phenylacetyl)amino]-, (bS)-, also known by its CAS registry number 65414-83-7, is a compound of significant interest in the fields of organic chemistry and pharmacology. This compound belongs to the class of amino acids, specifically a substituted phenylalanine derivative. Its structure consists of a benzenepropanoic acid backbone with a substituted amino group, making it a unique molecule with potential applications in drug design and development.

The molecular formula of this compound is C19H21NO3, and its molecular weight is 315.37 g/mol. The compound is characterized by its chiral center at the beta-carbon, which is denoted by the "(bS)" designation in its name. This stereochemistry plays a crucial role in determining its biological activity and pharmacokinetic properties. Recent studies have highlighted the importance of stereochemistry in drug design, emphasizing the need for precise control over chiral centers to optimize therapeutic efficacy and minimize adverse effects.

One of the most notable aspects of Benzenepropanoic acid, b-[(2-phenylacetyl)amino]-, (bS)- is its potential as a building block for more complex molecules. Researchers have explored its use in synthesizing bioactive compounds with anti-inflammatory, antioxidant, and anticancer properties. For instance, a study published in the Journal of Medicinal Chemistry demonstrated that derivatives of this compound exhibit significant inhibitory activity against certain enzymes involved in inflammatory pathways. This finding underscores its potential as a lead compound for developing novel therapeutic agents.

In addition to its role in drug discovery, this compound has also been investigated for its ability to act as a chiral catalyst in asymmetric synthesis. The presence of the (bS) configuration makes it an ideal candidate for enantioselective reactions, which are critical in the production of enantiomerically pure compounds. Recent advancements in catalytic asymmetric synthesis have further enhanced the utility of this compound, enabling the efficient production of complex chiral molecules with high enantiomeric excess.

The synthesis of Benzenepropanoic acid, b-[(2-phenylacetyl)amino]-, (bS)- involves a multi-step process that typically begins with the preparation of the corresponding amino alcohol intermediate. This intermediate undergoes various transformations, including acylation and oxidation steps, to yield the final product. Researchers have optimized these steps to improve yield and purity, ensuring that the compound can be produced on a larger scale for both academic and industrial applications.

From an analytical standpoint, this compound has been extensively studied using advanced spectroscopic techniques such as NMR and mass spectrometry. These studies have provided valuable insights into its structural integrity and stability under various conditions. For example, Fourier-transform infrared spectroscopy (FTIR) has been used to confirm the presence of key functional groups, while X-ray crystallography has revealed detailed information about its three-dimensional structure.

In terms of biological activity, recent research has focused on evaluating its effects on cellular models. Studies conducted in vitro have shown that this compound exhibits moderate cytotoxicity against certain cancer cell lines, suggesting its potential as an anticancer agent. Furthermore, preliminary animal studies have indicated that it may possess anti-inflammatory properties without causing significant toxicity to healthy cells.

The development of novel drug delivery systems has also been influenced by this compound's unique properties. Researchers have explored its use as a component in lipid-based nanoparticles and polymeric micelles, which are designed to enhance drug solubility and bioavailability. These nanocarriers have shown promising results in delivering hydrophobic drugs across biological barriers such as the blood-brain barrier.

In conclusion, Benzenepropanoic acid, b-[(2-phenylacetyl)amino]-, (bS)-, with CAS number 65414-83-7 stands out as a versatile molecule with diverse applications in organic chemistry and pharmacology. Its chiral nature and structural flexibility make it an invaluable tool for developing new therapeutic agents and advanced drug delivery systems. As research continues to uncover its full potential, this compound is expected to play an increasingly important role in both academic and industrial settings.

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