(S)-3-(2-((S)-1,3-dimethyl-2-oxoindolin-3-yl)acetyl)-4-phenyloxazolidin-2-one | 1360238-42-1

• 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: (S)-3-(2-((S)-1,3-dimethyl-2-oxoindolin-3-yl)acetyl)-4-phenyloxazolidin-2-one
• 英文别名: (4S)-3-[2-[(3S)-1,3-dimethyl-2-oxoindol-3-yl]acetyl]-4-phenyl-1,3-oxazolidin-2-one
• CAS: 1360238-42-1
• 化学式: C₂₁H₂₀N₂O₄
• 分子量: 364.401
• InChiKey: CNRWYPANOUPSCT-UTKZUKDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(1,3-dimethyl-2-oxoindolin-3-yl)acetic acid 、 (S)-4-苯基-2-恶唑烷酮 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 26.5h， 以45%的产率得到(S)-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 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.