ethyl 5-methoxy-1,3-dimethyl-2-oxoindoline-3-carboxylate | 1236055-95-0

• 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: ethyl 5-methoxy-1,3-dimethyl-2-oxoindoline-3-carboxylate
• 英文别名: ethyl 1,3-dimethyl-5-methoxy-2-oxoindoline-3-carboxylate；Ethyl 5-methoxy-1,3-dimethyl-2-oxoindoline-3-carboxylate；ethyl 5-methoxy-1,3-dimethyl-2-oxoindole-3-carboxylate
• CAS: 1236055-95-0
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: JIBZLILGLILJNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl 3-((4-methoxyphenyl)(methyl)amino)-2-methyl-3-oxopropanoate 在 copper(I) oxide 作用下， 以 neat (no solvent) 为溶剂， 以96%的产率得到ethyl 5-methoxy-1,3-dimethyl-2-oxoindoline-3-carboxylate
  参考文献：
  名称：

  在无溶剂和有氧条件下通过金属催化的分子内CC键形成原子经济合成羟吲哚

  摘要：

  各种取代的苯甲酸酯和吡啶基酰胺与金属盐作为催化剂的原子经济的直接CC键形成反应，获得了不同取代的羟吲哚，其中金属盐包括Cu2O，FeCl3，Fe2O3，TiO2，ZnO，...

  DOI：

  10.1039/c5gc00703h

文献信息

• Synthesis of oxindolesvia visible light photoredox catalysis
  作者：Xuhui Ju、Yan Liang、Pingjing Jia、Weifei Li、Wei Yu

  DOI：10.1039/c1ob06652h

  日期：——

  2-Electron-withdrawing-group-substituted 2-bromoanilides can be converted to the corresponding 3,3-disubstituted oxindoles with high efficiency under visible light irradiation by using fac-Ir(ppy)3 as the photoredox catalyst. This protocol is suitable for the synthesis of oxindoles with chloro and bromo atoms attached to the phenyl ring.

  在可见光照射下，通过将2-抽电子基团取代的2-溴苯胺可以高效转化为相应的3,3-二取代的羟吲哚。 fac -Ir（ppy）3作为光氧化还原催化剂。该方案适用于合成具有连接在苯环上的氯和溴原子的羟吲哚。
• Atom economical synthesis of oxindoles by metal-catalyzed intramolecular C–C bond formation under solvent-free and aerobic conditions
  作者：Se In Son、Won Koo Lee、Jieun Choi、Hyun-Joon Ha

  DOI：10.1039/c5gc00703h

  日期：——

  Diversely substituted oxindoles were obtained from atom economical direct C-C bond formation reactions of various substituted anilides and pyridinylamides with metal salts as catalysts including Cu2O, FeCl3, Fe2O3, TiO2, ZnO,...

  各种取代的苯甲酸酯和吡啶基酰胺与金属盐作为催化剂的原子经济的直接CC键形成反应，获得了不同取代的羟吲哚，其中金属盐包括Cu2O，FeCl3，Fe2O3，TiO2，ZnO，...
• First C−H Activation Route to Oxindoles using Copper Catalysis
  作者：Johannes E. M. N. Klein、Alexis Perry、David S. Pugh、Richard J. K. Taylor

  DOI：10.1021/ol1012668

  日期：2010.8.6

  The preparation of 3,3-disubstituted oxindoles by a formal C-H, Ar-H coupling of anilides is described. Highly efficient conditions have been Identified using catalytic (5 mol %) Cu(OAc)(2)center dot H(2)O with atmospheric oxygen as the reoxidant; no additional base is required, and the reaction can be run in toluene or mesitylene. Optimization studies are reported together with a scope and limitation investigation based on variation of the anilide precursors. The application of this methodology to prepare a key Intermediate for the total synthesis of the anticancer, analgesic oxindole alkaloid Horsfiline is also described.
• Intramolecular Dehydrogenative Coupling Approach to 2‐Oxindoles Using Fe(OAc) ₂ /NaI/Na ₂ S ₂ O ₈
  作者：Junyan Zhao、Xun Song、Dong Li、Jinfeng Zhao、Jingping Qu、Yuhan Zhou

  DOI：10.1002/ejoc.202001111

  日期：2020.10.31

  A novel method for the synthesis of 2‐oxindoles from 1,3‐dicarbonyl compounds based on ferrous salt and iodide catalyst was described. Through a new catalytic oxidation system, the intramolecular dehydrogenation coupling reaction was completed by using catalytic amount of iodine.

  描述了一种基于亚铁盐和碘化物催化剂由1,3-二羰基化合物合成2-吲哚的新方法。通过新的催化氧化体系，利用催化量的碘完成了分子内脱氢偶联反应。