(R)-3-(2-((S)-1,3-dimethyl-2-oxoindolin-3-yl)acetyl)-4-phenyloxazolidin-2-one | 1360238-43-2

• 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)-3-(2-((S)-1,3-dimethyl-2-oxoindolin-3-yl)acetyl)-4-phenyloxazolidin-2-one
• CAS: 1360238-43-2
• 化学式: C₂₁H₂₀N₂O₄
• 分子量: 364.401
• InChiKey: CNRWYPANOUPSCT-UWJYYQICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-3-(2-((S)-1,3-dimethyl-2-oxoindolin-3-yl)acetyl)-4-phenyloxazolidin-2-one 在 双氧水 、 lithium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 18.0h， 以90%的产率得到(S)-(+)-2-(1,3-dimethyl-2-oxoindolin-3-yl)acetic acid
  参考文献：
  名称：

  Absolute configuration assignment of oxindole derivatives by vibrational circular dichroism exciton coupling

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2016.06.004
• 作为产物：
  描述：

  2-(1,3-dimethyl-2-oxoindolin-3-yl)acetic acid 、 (R)-4-苯基-2-唑烷酮 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， 生成 (R)-3-(2-((S)-1,3-dimethyl-2-oxoindolin-3-yl)acetyl)-4-phenyloxazolidin-2-one 、 (R)-3-(2-((R)-1,3-dimethyl-2-oxoindolin-3-yl)acetyl)-4-phenyloxazolidin-2-one
  参考文献：
  名称：

  Absolute configuration assignment of oxindole derivatives by vibrational circular dichroism exciton coupling

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2016.06.004

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.