dioxindole-3-propionamide | 133603-34-6

• 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: dioxindole-3-propionamide
• 英文别名: 3-(3-hydroxy-2-oxo-1H-indol-3-yl)propanamide
• CAS: 133603-34-6
• 化学式: C₁₁H₁₂N₂O₃
• 分子量: 220.228
• InChiKey: PYGCTEXLLFKMRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.09
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  92.42
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3-吲哚丙酸 在 溴代叔丁烷 、 氨 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 24.0h， 生成 dioxindole-3-propionamide
  参考文献：
  名称：

  An improved synthesis of dioxindole-3-propionic acid and some transformations of the C-3 hydroxyl group

  摘要：

  Dioxindole-3-propionic acid lactone (3) is obtained in 80% yield by oxidative cyclization of indole-3-propionic acid with t-BuBr/DMSO. In the presence of 18-crown-6 in DMSO, KCN opens the spirolactone ring of 3 at C-3 with the formation of 3-cyanooxindole-3-propionic acid (4a) in 14% yield. Methanolysis of the lactone is strongly promoted by DMAP, and the resulting 3-hydroxy ester (5) is converted into the 3-fluoro ester (6) with methyl DAST. Every attempt to isolate 3-fluorooxindole-3-propionic acid resulted in rapid intramolecular displacement of fluorine by the free carboxyl group to reform the spirolactone. The 3-hydroxy ester is converted into the 3-chloro ester (9) with SOCl2/Et3N. The halogen is readily displaced by nucleophiles (e.g., N3-, CN-, NH3, AcO-, H2O) to generate the corresponding methyl 3-X-oxindole-3-propionate. Saponification of the ester function provides the corresponding 3-X-oxindole-3-propionic acid. Acetylation of the 3-hydroxy ester provides a separable mixture of the O-acetyl (16) and N-acetyl (17) derivatives. As in the case of 3, the O-acetyl derivative undergoes hydrogenolysis at C-3, while the 3-hydroxyl function is stable to removal by hydrogenolysis.

  DOI：

  10.1021/jo00011a035

文献信息

• LABROO, RITA B.;LABROO, VIRENDER M.;KING, MICHAEL M.;COHEN, LOUIS A., J. ORG. CHEM., 56,(1991) N1, C. 3637-3642
  作者：LABROO, RITA B.、LABROO, VIRENDER M.、KING, MICHAEL M.、COHEN, LOUIS A.

  DOI：——

  日期：——
• An improved synthesis of dioxindole-3-propionic acid and some transformations of the C-3 hydroxyl group
  作者：Rita B. Labroo、Virender M. Labroo、Michael M. King、Louis A. Cohen

  DOI：10.1021/jo00011a035

  日期：1991.5

  Dioxindole-3-propionic acid lactone (3) is obtained in 80% yield by oxidative cyclization of indole-3-propionic acid with t-BuBr/DMSO. In the presence of 18-crown-6 in DMSO, KCN opens the spirolactone ring of 3 at C-3 with the formation of 3-cyanooxindole-3-propionic acid (4a) in 14% yield. Methanolysis of the lactone is strongly promoted by DMAP, and the resulting 3-hydroxy ester (5) is converted into the 3-fluoro ester (6) with methyl DAST. Every attempt to isolate 3-fluorooxindole-3-propionic acid resulted in rapid intramolecular displacement of fluorine by the free carboxyl group to reform the spirolactone. The 3-hydroxy ester is converted into the 3-chloro ester (9) with SOCl2/Et3N. The halogen is readily displaced by nucleophiles (e.g., N3-, CN-, NH3, AcO-, H2O) to generate the corresponding methyl 3-X-oxindole-3-propionate. Saponification of the ester function provides the corresponding 3-X-oxindole-3-propionic acid. Acetylation of the 3-hydroxy ester provides a separable mixture of the O-acetyl (16) and N-acetyl (17) derivatives. As in the case of 3, the O-acetyl derivative undergoes hydrogenolysis at C-3, while the 3-hydroxyl function is stable to removal by hydrogenolysis.