(2S)-3-phenyl-2-(pyrazin-2-ylformamido)propanoic acid

• ChemBase编号: 177122
• 分子式: C14H13N3O3
• 平均质量: 271.27132
• 单一同位素质量: 271.09569129
• SMILES: c1ncc(nc1)C(=O)N[C@@H](Cc1ccccc1)C(=O)O
• Canonical SMILES: OC(=O)[C@@H](NC(=O)c1nccnc1)Cc1ccccc1
• InChI: InChI=1S/C14H13N3O3/c18-13(12-9-15-6-7-16-12)17-11(14(19)20)8-10-4-2-1-3-5-10/h1-7,9,11H,8H2,(H,17,18)(H,19,20)/t11-/m0/s1
• InChIKey: DWYZPDHMMZGQAP-NSHDSACASA-N

名称和登记号

名称

• IUPAC标准名: (2S)-3-phenyl-2-(pyrazin-2-ylformamido)propanoic acid
• IUPAC传统名: (2S)-3-phenyl-2-(pyrazin-2-ylformamido)propanoic acid
• 别名: N-(2-pyrazinylcarbonyl)-L-phenylalanine; 3-Phenyl-2-[(pyrazine-2-carbonyl)amino]propionic Acid; N-Pyrazinylcarbonyl-L-phenylalanine

登记号

• CAS号: 114457-94-2
• PubChem SID: 164233032
• PubChem CID: 15042559

理论计算性质

• Acid pKa: 3.2107542
• 质子受体: 5
• 质子供体: 2
• LogD (pH = 5.5): -1.5661561
• LogD (pH = 7.4): -2.7424119
• Log P: 0.70114154
• 摩尔折射率: 70.5448 cm^3
• 极化性: 27.049767 Å^3
• 极化表面积: 92.18 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSo; Methanol
• 外观: Light Beige Solid
• 熔点: 148-150°C

安全信息

• 保存条件: Refrigerator

详细说明

Toronto Research Chemicals - P841500

Used for the synthesis of Bortezomib from L-phenylalanine via dipeptidyl boronic acid ester intermediates.

参考文献

• Zhu, Y., et al.: J. Med. Chem., 52, 4192 (2009)