N-benzoyl-(4'-nitro)phenylalanine | 101468-97-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-benzoyl-(4'-nitro)phenylalanine
• 英文别名: N-benzoyl-4-nitro-DL-phenylalanine；N-Benzoyl-4-nitro-DL-phenylalanin；N-Benzoyl-4-nitrophenylalanine；2-benzamido-3-(4-nitrophenyl)propanoic acid
• CAS: 101468-97-7
• 化学式: C₁₆H₁₄N₂O₅
• 分子量: 314.298
• InChiKey: VPKNYNJAINDWNE-UHFFFAOYSA-N

物化性质

• 熔点：
  200-202 °C
• 沸点：
  619.8±50.0 °C(Predicted)
• 密度：
  1.364±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-benzoyl-(4'-nitro)phenylalanine 在 acylase-substance from pseudomonas 作用下， 生成 4-硝基-L-苯丙氨酸
  参考文献：
  名称：

  Kameda et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1958, vol. 78, p. 767

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl (N-benzoyl)-4'-nitrophenylalaninate 在 sodium hydroxide 作用下， 反应 0.58h， 生成 N-benzoyl-(4'-nitro)phenylalanine
  参考文献：
  名称：

  Sikdar, Atul P.; Chetri, Ajoy B.; Das, Pranab J., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 11, p. 2878 - 2881

  摘要：

  DOI：

文献信息

• Synthesis of fluorinated α-amino ketones part I: α-benzamidoalkyl mono- di- and trifluoromethyl ketones
  作者：Michael Kolb、Jacqueline Barth、Bernhard Neises

  DOI：10.1016/s0040-4039(00)84319-1

  日期：1986.1

  2-Phenyl-5(4H)-oxazolones, obtained from α-amino acids, are reacted with di- and trifluoro acetic anhydride by a modified Dakin-West procedure to yield in a one-pot reaction α-benzamidoalkyl-di- and trifluoromethyl ketones in good yields. The monofluoromethyl analogues were also prepared from α-amino acids, however the use of the highly toxic fluoroacetic anhydride was avoided. The key step is the

  由α-氨基酸制得的2-苯基-5（4H）-恶唑酮通过改良的Dakin-West方法与二氟和三氟乙酸酐反应，以一锅法反应生成α-苯甲酰胺基烷基二氟和三氟甲基酮收率高。单氟甲基类似物也由α-氨基酸制备，但是避免了使用剧毒的氟乙酸酐。关键步骤是在相应的溴甲基酮上进行卤素交换反应。
• Ring opening with kinetic resolution of azlactones by Ti-TADDOLates
  作者：Konstanze Gottwald、Dieter Seebach

  DOI：10.1016/s0040-4020(98)01064-3

  日期：1999.1

  The kinetic resolution of azlactones by the Lewis-acid-mediated transfer of an isopropoxide ligand from the chiral ligand sphere of Ti-TADDOLate is described. The reactions proceed with in-situ racemization of the starting material to afford highly enantiomerically enriched N-benzoyl-amino acid isopropylesters (er > 95:5 after recrystallization). The absolute configuration of the major enantiomer of N-benzoyl-phenylalanine isopropyl ester and its analogs with other aromatic substituents was shown to be (S)-(+) when the (R,R)-Ti-TADDOLate was employed. Only benzyl-substituted azlactones can be opened enantioselectively by the method described here. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Some p-Arsenic-substituted Derivatives of Phenylalanine¹
  作者：W. L. Bressler、Leon S. Ciereszko

  DOI：10.1021/ja01613a090

  日期：1955.4
• Kameda et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1958, vol. 78, p. 767
  作者：Kameda et al.

  DOI：——

  日期：——
• Sikdar, Atul P.; Chetri, Ajoy B.; Das, Pranab J., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 11, p. 2878 - 2881
  作者：Sikdar, Atul P.、Chetri, Ajoy B.、Das, Pranab J.

  DOI：——

  日期：——