(+)-(R)-2-cyano-2-(1H-indol-3-yl)propanoic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (+)-(R)-2-cyano-2-(1H-indol-3-yl)propanoic acid
• 英文别名: (2R)-2-cyano-2-(1H-indol-3-yl)propanoic acid
• 化学式: C₁₂H₁₀N₂O₂
• 分子量: 214.224
• InChiKey: CRYWSDDVLLWSHR-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  76.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(+)-1-苯基乙醇 、 (+)-(R)-2-cyano-2-(1H-indol-3-yl)propanoic acid 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以53%的产率得到(+)-(R)-1-phenylethyl (R)-2-cyano-2-(1H-indol-3-yl)propanoate
  参考文献：
  名称：

  2-Cyano-2-indolylpropanoic acid as a chiral derivatizing agent for the absolute configuration assignment of secondary alcohols and primary amines by 1 H NMR and VCD

  摘要：

  A convenient approach for the absolute configuration assignment of secondary alcohols in the (8R,1'R,2'S,5'R)-15,25, (8S,1'R,2'S,5'R)-15,25, (8R,1'R)-21-24, and (8S,l'R)-21-24 ester series, and of primary amines in the (8R,1'R)-32-37 and (8S,1'R)-32-37 amide series, by means of H-1 NMR and VCD spectroscopy, using 2-cyano-2-indolylpropanoic acid as a chiral derivatizing agent is presented. DFT calculations were carried out to demonstrate the anisotropic effect of the indole skeleton on the chiral alcohol or the amine fragment. Vibrational circular dichroism (VCD) measurements of the above series indicated a VCD bisignated couplet resulting from the interaction of the ester carbonyl group and the -CN group. The absolute configuration assignments were further tested by X-ray diffraction analysis. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.04.011
• 作为产物：
  描述：

  2-氰基-2-吲哚-3-基-丙酸 在 4-二甲氨基吡啶 、 水 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 28.5h， 生成 (+)-(R)-2-cyano-2-(1H-indol-3-yl)propanoic acid
  参考文献：
  名称：

  2-Cyano-2-indolylpropanoic acid as a chiral derivatizing agent for the absolute configuration assignment of secondary alcohols and primary amines by 1 H NMR and VCD

  摘要：

  A convenient approach for the absolute configuration assignment of secondary alcohols in the (8R,1'R,2'S,5'R)-15,25, (8S,1'R,2'S,5'R)-15,25, (8R,1'R)-21-24, and (8S,l'R)-21-24 ester series, and of primary amines in the (8R,1'R)-32-37 and (8S,1'R)-32-37 amide series, by means of H-1 NMR and VCD spectroscopy, using 2-cyano-2-indolylpropanoic acid as a chiral derivatizing agent is presented. DFT calculations were carried out to demonstrate the anisotropic effect of the indole skeleton on the chiral alcohol or the amine fragment. Vibrational circular dichroism (VCD) measurements of the above series indicated a VCD bisignated couplet resulting from the interaction of the ester carbonyl group and the -CN group. The absolute configuration assignments were further tested by X-ray diffraction analysis. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.04.011

文献信息

• 2-Cyano-2-indolylpropanoic acid as a chiral derivatizing agent for the absolute configuration assignment of secondary alcohols and primary amines by 1 H NMR and VCD
  作者：Claudia I. Bautista-Hernández、Nayely Trejo-Carbajal、Erick A. Zúñiga-Estrada、Alberto Aristeo-Dominguez、Myriam Meléndez-Rodríguez、Oscar R. Suárez-Castillo、Maricruz Sánchez-Zavala、Julián Cruz-Borbolla、Martha S. Morales-Ríos、Pedro Joseph-Nathan

  DOI：10.1016/j.tetasy.2017.04.011

  日期：2017.6

  A convenient approach for the absolute configuration assignment of secondary alcohols in the (8R,1'R,2'S,5'R)-15,25, (8S,1'R,2'S,5'R)-15,25, (8R,1'R)-21-24, and (8S,l'R)-21-24 ester series, and of primary amines in the (8R,1'R)-32-37 and (8S,1'R)-32-37 amide series, by means of H-1 NMR and VCD spectroscopy, using 2-cyano-2-indolylpropanoic acid as a chiral derivatizing agent is presented. DFT calculations were carried out to demonstrate the anisotropic effect of the indole skeleton on the chiral alcohol or the amine fragment. Vibrational circular dichroism (VCD) measurements of the above series indicated a VCD bisignated couplet resulting from the interaction of the ester carbonyl group and the -CN group. The absolute configuration assignments were further tested by X-ray diffraction analysis. (C) 2017 Elsevier Ltd. All rights reserved.