(Z)-methyl 2-benzamido-3-(1H-imidazol-5-yl)acrylate | 1015244-09-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-methyl 2-benzamido-3-(1H-imidazol-5-yl)acrylate
• 英文别名: (Z)-2-benzamido-4(5)-N-imidazolylpropenoic acid methyl ester；methyl (Z)-2-benzamido-3-(1H-imidazol-5-yl)prop-2-enoate
• CAS: 1015244-09-3
• 化学式: C₁₄H₁₃N₃O₃
• 分子量: 271.276
• InChiKey: OVCSDFNQZWABQD-GHXNOFRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  84.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-methyl 2-benzamido-3-(1H-imidazol-5-yl)acrylate 在 甲烷磺酸 、 C₂₇H₄₂P₂Rh⁽¹⁺⁾*ClO₄^(1-) 、 氘 作用下， 以 氘代甲醇-d 为溶剂， 生成
  参考文献：
  名称：

  Histidine and deuterium-labelled histidine by asymmetric catalytic reduction and assignment of the absolute stereochemistry by neutron diffraction

  摘要：

  We describe an efficient and convenient route for the preparation of enantiomerically pure D-labelled histidine by asymmetric hydrogenation with a Rh-diphosphine complex in the presence of strong non-coordinating acids. A single-crystal neutron diffraction study of the selectively dideuterated N-benzoyl-histidine methyl ester, tetrafluoroborate salt determined the absolute stereochemistry. This allowed us to clarify the role of H(+) in the whole reduction process. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.03.044

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.
• Histidine and deuterium-labelled histidine by asymmetric catalytic reduction and assignment of the absolute stereochemistry by neutron diffraction
  作者：A. Albinati、E. Cesarotti、S.A. Mason、I. Rimoldi、S. Rizzato、D. Zerla

  DOI：10.1016/j.tetasy.2010.03.044

  日期：2010.5

  We describe an efficient and convenient route for the preparation of enantiomerically pure D-labelled histidine by asymmetric hydrogenation with a Rh-diphosphine complex in the presence of strong non-coordinating acids. A single-crystal neutron diffraction study of the selectively dideuterated N-benzoyl-histidine methyl ester, tetrafluoroborate salt determined the absolute stereochemistry. This allowed us to clarify the role of H(+) in the whole reduction process. (C) 2010 Elsevier Ltd. All rights reserved.