methyl 3-chlorooxindole-3-propionate | 133603-29-9

• 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: methyl 3-chlorooxindole-3-propionate
• 英文别名: methyl 3-(3-chloro-2-oxo-1H-indol-3-yl)propanoate
• CAS: 133603-29-9
• 化学式: C₁₂H₁₂ClNO₃
• 分子量: 253.685
• InChiKey: FULASXDJMFSCRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-chlorooxindole-3-propionate 在 sodium azide 、 15-冠醚-5 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以84.8%的产率得到methyl 3-azidooxindole-3-propionate
  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
• 作为产物：
  描述：

  3-吲哚丙酸 在 4-二甲氨基吡啶 、 氯化亚砜 、 溴代叔丁烷 、 二甲基亚砜 、 三乙胺 作用下， 生成 methyl 3-chlorooxindole-3-propionate
  参考文献：
  名称：

  1-Thia-4,7-diaza-spiro[4.4]nonane-3,6-dione: A Structural Motif for 5-hydroxytryptamine 6 Receptor Antagonism

  摘要：

  A series of potent 5‐hydroxytryptamine 6 (5‐HT6) receptor antagonists based on 1‐thia‐4,7‐diaza‐spiro[4.4]nonane‐3,6‐dione motif has been disclosed. Enantiomers of potent racemate compound 8a (Ki = 26 nm) displayed difference in activity (Ki of 15 nm versus 855 nm) signaling the influence of the stereochemistry of the chiral center on potency. In addition, the potent enantiomer displayed significant selectivity in biological activities over several related family members.

  DOI：

  10.1111/cbdd.12240

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：——