2-{3-oxo-3-[(4R)-4-(1-pyrrolidinylcarbonyl)-1,3-thiazolidin-3-yl]propyl}-1H-isoindole-1,3(2H)-dione | 188587-38-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-{3-oxo-3-[(4R)-4-(1-pyrrolidinylcarbonyl)-1,3-thiazolidin-3-yl]propyl}-1H-isoindole-1,3(2H)-dione
• 英文别名: 2-[3-oxo-3-[(4R)-4-(pyrrolidine-1-carbonyl)-1,3-thiazolidin-3-yl]propyl]isoindole-1,3-dione
• CAS: 188587-38-4
• 化学式: C₁₉H₂₁N₃O₄S
• 分子量: 387.459
• InChiKey: XYJDJICFLXSCTJ-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-{3-oxo-3-[(4R)-4-(1-pyrrolidinylcarbonyl)-1,3-thiazolidin-3-yl]propyl}-1H-isoindole-1,3(2H)-dione 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 7.0h， 以63%的产率得到2-{3-oxo-3-[(1R,4R)-1-oxido-4-(1-pyrrolidinylcarbonyl)-1,3-thiazolidin-3-yl]propyl}-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  Stereoselective sulfoxide formation from a thioproline derivative

  摘要：

  Oxidation of the PEP inhibitor, thioprolylpyrrolidine derivative 3 affords a mixture of the two possible trans- and cis-sulfoxide isomers 4 and 5. 3-Chloroperbenzoic acid oxidation resulted almost exclusive formation of the trans-isomer (a-sulfoxide, 4, d.e. >99% in CHCl3), whereas when NaIO4 was used the cis isomer (beta-sulfoxide, 5) was also obtained, the ratio of the isomers varying with the reaction conditions applied. The structures of the separated isomers 4 and 5 were assigned on the basis of the aromatic solvent-induced shifts (ASIS) in the NMR spectra. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00134-9
• 作为产物：
  描述：

  3-(N-苯二甲酰亚氨基)丙酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-{3-oxo-3-[(4R)-4-(1-pyrrolidinylcarbonyl)-1,3-thiazolidin-3-yl]propyl}-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  Stereoselective sulfoxide formation from a thioproline derivative

  摘要：

  Oxidation of the PEP inhibitor, thioprolylpyrrolidine derivative 3 affords a mixture of the two possible trans- and cis-sulfoxide isomers 4 and 5. 3-Chloroperbenzoic acid oxidation resulted almost exclusive formation of the trans-isomer (a-sulfoxide, 4, d.e. >99% in CHCl3), whereas when NaIO4 was used the cis isomer (beta-sulfoxide, 5) was also obtained, the ratio of the isomers varying with the reaction conditions applied. The structures of the separated isomers 4 and 5 were assigned on the basis of the aromatic solvent-induced shifts (ASIS) in the NMR spectra. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00134-9