1-Phenyl-3-methyl-oxindol-3-essigsaeure | 3450-97-3

• 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: 1-Phenyl-3-methyl-oxindol-3-essigsaeure
• 英文别名: 3-Methyl-2-oxo-1-phenyl-indolin-3-essigsaeure；(3-methyl-2-oxo-1-phenyl-2,3-dihydro-indol-3-yl)-acetic acid；2-(3-Methyl-2-oxo-1-phenylindol-3-yl)acetic acid；2-(3-methyl-2-oxo-1-phenylindol-3-yl)acetic acid
• CAS: 3450-97-3
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: QDVBMPZCETWEJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-4-苯基-2-恶唑烷酮 、 1-Phenyl-3-methyl-oxindol-3-essigsaeure 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 26.5h， 以14%的产率得到(S)-3-(2-((R)-3-methyl-2-oxo-1-phenylindolin-3-yl)-acetyl)-4-phenyloxazolidin-2-one
  参考文献：
  名称：

  Absolute configuration assignment of 3-oxindolylacetyl-4-phenyloxazolidinone derivatives

  摘要：

  The straightforward determination of the absolute configuration of 2-oxo-3-indolylacetic acid derivatives 5a-e, based on analysis of the H-1 NMR spectra of their oxindolylacetyl-phenyloxazolidinones 6a-e, is described. The conformational preferences for two diastereomeric amides were calculated by DFT, which matched well with the experimental results, while X-ray diffraction analysis allowed us to validate the methodology. Independent absolute configuration evidence was also obtained by vibrational circular dichroism. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.11.018

文献信息

• Absolute configuration assignment of 3-oxindolylacetyl-4-phenyloxazolidinone derivatives
  作者：Oscar R. Suárez-Castillo、Myriam Meléndez-Rodríguez、Luis E. Castelán-Duarte、Erick A. Zúñiga-Estrada、Julián Cruz-Borbolla、Martha S. Morales-Ríos、Pedro Joseph-Nathan

  DOI：10.1016/j.tetasy.2011.11.018

  日期：2011.12

  The straightforward determination of the absolute configuration of 2-oxo-3-indolylacetic acid derivatives 5a-e, based on analysis of the H-1 NMR spectra of their oxindolylacetyl-phenyloxazolidinones 6a-e, is described. The conformational preferences for two diastereomeric amides were calculated by DFT, which matched well with the experimental results, while X-ray diffraction analysis allowed us to validate the methodology. Independent absolute configuration evidence was also obtained by vibrational circular dichroism. (C) 2011 Elsevier Ltd. All rights reserved.