N-Benzoyl-p-nitro-D-phenylalanine | 76684-78-1

• 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-p-nitro-D-phenylalanine
• 英文别名: N-benzoyl-4-nitro-D-phenylalanine；N-Benzoyl-4-nitro-D-phenylalanin；(2R)-2-benzamido-3-(4-nitrophenyl)propanoic acid
• CAS: 76684-78-1
• 化学式: C₁₆H₁₄N₂O₅
• 分子量: 314.298
• InChiKey: VPKNYNJAINDWNE-CQSZACIVSA-N

物化性质

• 熔点：
  160-162 °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-p-nitro-D-phenylalanine 在 乙醇 、 钯 作用下， 生成 N-Benzoyl-p-amino-D-phenylalanine
  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：

  (Z)-2-苯酰胺-3-(4-硝基苯基)丙烯酸 在 BF4 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 N-Benzoyl-p-nitro-D-phenylalanine
  参考文献：
  名称：

  Asymmetric Synthesis XXVIII: Novel Chiral Aminophosphine Phosphinite Ligand and Its Application in Homogenous Catalytic Asymmetric Hydrogenation of Dehydroamino Acid Derivatives

  摘要：

  新型手性氨基膦膦酸酯DPAMPP是由(1S,2R)-1,2-二苯基-2-氨基甲醇设计和合成的。其阳离子铑配合物被发现是一种优良的催化剂，能够对脱氨基酸进行优异的选择性氢化（对映体过量超过95.0%）。

  DOI：

  10.1055/s-1998-1821

文献信息

• Aminophosphine Phosphinites Derived from Chiral 1,2-Diphenyl-2-aminoethanols: Synthesis and Application in Rhodium-Catalyzed Asymmetric Hydrogenation of Dehydroamino Acid Derivatives
  作者：Rongliang Lou、Aiqiao Mi、Yaozhong Jiang、Yong Qin、Zhi Li、Fangmin Fu、Albert S.C Chan

  DOI：10.1016/s0040-4020(00)00481-6

  日期：2000.8

  A series of chiral aminophosphine phosphinites DPAMPPs was synthesized from optically active 1,2-diphenyl-2-aminoethanols. The erythro-DPAMPPs were found to serve as excellent ligands for rhodium-catalyzed asymmetric hydrogenation of dehydroamino acid derivatives. For an array of dehydroamino acid precursors, remarkably high enantioselectivity (up to 98.4% e.e.) and reactivity (the ratio of substrate/catalyst

  由旋光的1,2-二苯基-2-氨基乙醇合成了一系列手性氨基膦次膦酸酯DPAMPP。所述赤发现-DPAMPPs以作为脱氢氨基酸衍生物的铑催化的不对称氢化优异的配体。对于一系列脱氢氨基酸前体，观察到非常高的对映选择性（高达98.4％ee）和反应性（高达10000的底物/催化剂比例）。研究和讨论了控制对映选择性的一些因素。
• Unusual amino acids III. Asymmetric synthesis of 3-arylalanines
  作者：Stefan Taudien、Klaus Schinkowski、Hans-Walter Krause

  DOI：10.1016/s0957-4166(00)86017-6

  日期：1993.1

  21 (Z)-alpha-N-benzoylamino-beta-arylacrylic acids and their esters were prepared by known procedures and hydrogenated to the corresponding optically active alpha-benzoyl-beta-arylalanine derivatives with optical yields in the range of 82-95% ee using the cationic rhodium complex of ''PROPRAPHOS'' as the chiral catalyst No electronical influences of the substituents at the aryl moiety on the enantioselectivity were observed but a sterical one, proved by X-ray crystallographic analysis and computer-aided modellings. Deacylation of the hydrogenated spezies produced the hydrochlorides of the 3-arylalanines attended by a partial racemisation In this case the hydrogenation of urethane type protected dehydroaminoacid derivatives seems to be the alternative.