triethyl (2'R,3S,3'R,4's,5'S)-2,2''-dioxodispiro[indoline-3,1'-cyclopentane-2',3''-indoline]-3',4',5'-tricarboxylate | 1585206-66-1

• 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: triethyl (2'R,3S,3'R,4's,5'S)-2,2''-dioxodispiro[indoline-3,1'-cyclopentane-2',3''-indoline]-3',4',5'-tricarboxylate
• CAS: 1585206-66-1
• 化学式: C₂₈H₂₈N₂O₈
• 分子量: 520.539
• InChiKey: BJZHFAKIDWDDFH-IGIDYPRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.32
• 重原子数：
  38.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  137.1
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  1-carbethoxymethyl-4-dimethylaminopyridinium bromide 、 (2-oxo-1,2-dihydro-indol-3-ylidene)-acetic acid ethyl ester 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以65%的产率得到triethyl (2'R,3S,3'R,4's,5'S)-2,2''-dioxodispiro[indoline-3,1'-cyclopentane-2',3''-indoline]-3',4',5'-tricarboxylate
  参考文献：
  名称：

  Synthesis of complex dispirocyclopentanebisoxindoles via cycloaddition reactions of 4-dimethylamino-1-alkoxycarbonylmethylpyridinium bromides with 2-oxoindolin-3-ylidene derivatives

  摘要：

  The cycloaddition reactions of 4-dimethylamino-1-alkoxycarbonylmethylpyridinium bromides with various 2-oxoindolin-3-ylidene derivatives in ethanol in the presence of triethylamine afforded the unprecedented dispirocyclopentanebisoxindole derivatives in good yields and in high diastereoselectivity. Under similar reaction conditions, the reactions of 1-alkoxycarbonylmethylpyridinium bromides with 3-phenacylideneoxindoles only resulted in 4-oxo-3-(2-oxoindolin-3-ylidene)-4-arylbutanoates. The stereochemistry of the complex spirooxindoles was established by H-1 NMR data and single crystal structures. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.02.050