(R)-(+)-N-苯甲酰基组氨酸甲酯 | 1015244-12-8

• 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
• 中文名称: (R)-(+)-N-苯甲酰基组氨酸甲酯
• 英文名称: (R)-(+)-N-benzoylhistidine methyl ester
• 英文别名: methyl (2R)-2-benzamido-3-(1H-imidazol-5-yl)propanoate
• CAS: 1015244-12-8
• 化学式: C₁₄H₁₅N₃O₃
• 分子量: 273.291
• InChiKey: POUMRJPRROOAGQ-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  84.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (Z)-methyl 2-benzamido-3-(1H-imidazol-5-yl)acrylate 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 72.0h， 生成 (R)-(+)-N-苯甲酰基组氨酸甲酯 、 N-苄基-L-组氨酸甲酯
  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.