2-(1-methyl-3-ethyl-2-oxo-2,3-dihydro-1H-indol-3-yl)acetic acid | 1203474-60-5

• 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: 2-(1-methyl-3-ethyl-2-oxo-2,3-dihydro-1H-indol-3-yl)acetic acid
• CAS: 1203474-60-5
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: BWAZJDFTRHFZKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.79
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.61
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(1-methyl-3-ethyl-2-oxo-2,3-dihydro-1H-indol-3-yl)acetic acid 、 氯甲酸乙酯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 生成
  参考文献：
  名称：

  Absolute configuration determination of 2-(2-oxo-3-indolyl)acetamide derivatives

  摘要：

  We describe a reliable method for determining the absolute configuration of 2-(2-oxo-3-indolyl)acetamides based on analysis of the H-1 NMR spectra of their phenylethylamide diastereomers. The conformational preferences for two diastereomeric amides were calculated by DFT, which matched well with the experimental results. X-ray diffraction analysis allowed us to validate the method. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.09.017
• 作为产物：
  描述：

  methyl 2-(1-methyl-3-ethyl-2-oxo-2,3-dihydro-1H-indol-3-yl)acetate 在 水 、 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 1.5h， 以85%的产率得到2-(1-methyl-3-ethyl-2-oxo-2,3-dihydro-1H-indol-3-yl)acetic acid
  参考文献：
  名称：

  Absolute configuration determination of 2-(2-oxo-3-indolyl)acetamide derivatives

  摘要：

  We describe a reliable method for determining the absolute configuration of 2-(2-oxo-3-indolyl)acetamides based on analysis of the H-1 NMR spectra of their phenylethylamide diastereomers. The conformational preferences for two diastereomeric amides were calculated by DFT, which matched well with the experimental results. X-ray diffraction analysis allowed us to validate the method. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.09.017

文献信息

• Absolute configuration assignment of oxindole derivatives by vibrational circular dichroism exciton coupling
  作者：Claudia I. Bautista-Hernández、Reyna E. Cordero-Rivera、Erick A. Zúñiga-Estrada、Nayely Trejo-Carbajal、Myriam Meléndez-Rodríguez、Oscar R. Suárez-Castillo、Maricruz Sánchez-Zavala、Martha S. Morales-Ríos、Pedro Joseph-Nathan

  DOI：10.1016/j.tetasy.2016.06.004

  日期：2016.8

  A convenient and reliable approach for the absolute configuration assignment of oxindole derivatives 2a-m by vibrational circular dichroism (VCD) measurements and evaluation of the VCD bisignated couplet resulting from the interaction of the C2 and C9 carbonyl groups is presented. The absolute configuration assignments were further tested by H-1 NMR measurements and by X-ray diffraction analysis. (C) 2016 Elsevier Ltd. All rights reserved.