methyl dioxindole-3-propionate | 133603-25-5

• 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 dioxindole-3-propionate
• 英文别名: methyl 3-(3-hydroxy-2-oxoindolin-3-yl)propanoate；methyl 3-(3-hydroxy-2-oxo-1H-indol-3-yl)propanoate
• CAS: 133603-25-5
• 化学式: C₁₂H₁₃NO₄
• 分子量: 235.24
• InChiKey: AGJNZWMUJBSBIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.78
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.63
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl dioxindole-3-propionate 在 氯化亚砜 、 三乙胺 作用下， 以100%的产率得到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
• 作为产物：
  描述：

  3-吲哚丙酸 在 polystyrene 、 4-二甲氨基吡啶 溴代叔丁烷 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 生成 methyl dioxindole-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

文献信息

• Reductive Coupling of Isatins with α,β-Unsaturated Carbonyl Compounds by Low-Valent Titanium
  作者：Naoki Kise、Yuki Mitsui、Toshihiko Sakurai

  DOI：10.1246/bcsj.20210357

  日期：2022.1.15

  The reductive coupling of isatins with α,β-unsaturated carbonyl compounds by Zn-TiCl4 in THF at 0 °C gave one-to-one coupled products, 3-hydoxy-3-alkyloxindoles. The coupled products obtained from α,β-unsaturated esters were transformed to the corresponding spiro-γ-lactones by refluxing in cat. PPTS/benzene. The two-to-one coupled products, 3,3-bis(2-carbomethoxyethyl)oxindoles, were formed by the

  靛红与 α,β-不饱和羰基化合物在 0 °C 下通过 Zn-TiCl 4在 THF 中的还原偶联得到一对一的偶联产物，3-羟基-3-烷氧基吲哚。由α,β-不饱和酯获得的偶联产物通过在催化剂中回流转化为相应的螺-γ-内酯。PPTS/苯。2:1 偶联产物 3,3-双（2-碳甲氧基乙基）羟吲哚是通过 Zn-TiCl 4在 THF 中在 30 °C 下用丙烯酸甲酯还原靛红形成的。靛红与丙烯酸甲酯还原偶联得到的一对一偶联产物通过Zn-TiCl 4还原为3-(2-甲氧基乙基)羟吲哚在 30 °C 的 THF 中。将 3-(2- 碳甲氧基乙基) 羟吲哚加入丙烯腈中得到 3-(2- 碳甲氧基乙基)-3-(2-氰乙基) 羟吲哚。
• 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：——