(2R)-2-benzamido-3-(1H-imidazol-3-ium-5-yl)propanoate | 127063-22-3

• 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: (2R)-2-benzamido-3-(1H-imidazol-3-ium-5-yl)propanoate
• CAS: 127063-22-3
• 化学式: C₁₃H₁₃N₃O₃
• mdl: MFCD27879352
• 分子量: 259.265
• InChiKey: AUDPUFBIVWMAED-LLVKDONJSA-N

物化性质

• 沸点：
  662.3±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)：
  1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  95.1
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (Z)-2-benzamido-3-(1H-imidazol-5-yl)acrylic acid 在 [Rh(COD)2]ClO₄ tetrafluoroboric acid 、 氢气 作用下， 以 甲醇 、 乙醚 为溶剂， 19.84 ℃ 、100.0 kPa 条件下， 反应 120.0h， 生成 (2R)-2-benzamido-3-(1H-imidazol-3-ium-5-yl)propanoate 、 NΑ-苯甲酰-L-组氨酸
  参考文献：
  名称：

  Histidine and deuterium labelled histidine by asymmetric catalytic reduction with gaseous H2 or D2; the role of strong non-coordinating acids

  摘要：

  An efficient and convenient route for the preparation of natural and unnatural histidine by asymmetric hydrogenation with rhodium-phosphine complexes is described. The reductions were performed in the presence of HBF(4) to generate an essential imidazolyl cation. Stereoselective incorporation of D(2) in the alpha,beta-positions was obtained by catalytic deuteration in the presence of MeOD. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.12.013

文献信息

• Histidine and deuterium labelled histidine by asymmetric catalytic reduction with gaseous H2 or D2; the role of strong non-coordinating acids
  作者：E. Cesarotti、I. Rimoldi、D. Zerla、G. Aldini

  DOI：10.1016/j.tetasy.2007.12.013

  日期：2008.2

  An efficient and convenient route for the preparation of natural and unnatural histidine by asymmetric hydrogenation with rhodium-phosphine complexes is described. The reductions were performed in the presence of HBF(4) to generate an essential imidazolyl cation. Stereoselective incorporation of D(2) in the alpha,beta-positions was obtained by catalytic deuteration in the presence of MeOD. (c) 2008 Elsevier Ltd. All rights reserved.