methyl 2-(3-hydroxy-5-methyl-2-oxo-1H-indol-3-yl)prop-2-enoate | 1021359-55-6

• 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: methyl 2-(3-hydroxy-5-methyl-2-oxo-1H-indol-3-yl)prop-2-enoate
• CAS: 1021359-55-6
• 化学式: C₁₃H₁₃NO₄
• 分子量: 247.251
• InChiKey: VSBKASWKPVGPBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-(3-hydroxy-5-methyl-2-oxo-1H-indol-3-yl)prop-2-enoate 在 ammonium cerium(IV) nitrate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 0.08h， 以87%的产率得到methyl 2-(5-formyl-3-hydroxy-2-oxo-1H-indol-3-yl)prop-2-enoate
  参考文献：
  名称：

  A mild and efficient CAN mediated oxidation of Morita–Baylis–Hillman adducts of 5-methyl-N-alkylisatin to 5-formyl-N-alkylisatin

  摘要：

  A simple, mild and efficient CAN mediated oxidation of Morita-Baylis-Hillman adducts of 5-methyl-N-alkylisatins 1a-13a to 5-formyl-N-alkylisatins lb-13b under ambient reaction conditions is reported. Simple and isomerized 5-methyl-N-alkylisatin derivatives 1-4 have also been tested and failed to provide the corresponding formylated products. A plausible reaction mechanism has been proposed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.01.119

文献信息

• Cooperative Tertiary Phosphine/Palladium Catalyzed Nucleophilic Allylation between Morita‐Baylis‐Hillman Carbonates and Alkenes
  作者：Yue Li、Peng Chen、Zhi‐Chao Chen、Wei Du、Ying‐Chun Chen

  DOI：10.1002/ejoc.202200218

  日期：2022.9.6

  A nucleophilic allylation reaction between isatin-derived Morita–Baylis–Hillman carbonates and simple alkenes was developed via cooperative tertiary phosphine and palladium catalysis. The in situ generated onium salts and η1-allylpalladium species were finely assembled with exclusive linear selectivity, producing a spectrum of 3,3-disubstituted oxindoles in moderate to good yields.

  通过协同叔膦和钯催化开发了靛红衍生的 Morita-Baylis-Hillman 碳酸盐和简单烯烃之间的亲核烯丙基化反应。原位生成的鎓盐和 η 1 -烯丙基钯物质以独特的线性选择性精细组装，以中等至良好的产率产生一系列 3,3-二取代羟吲哚。
• A mild and efficient CAN mediated oxidation of Morita–Baylis–Hillman adducts of 5-methyl-N-alkylisatin to 5-formyl-N-alkylisatin
  作者：Ponnusamy Shanmugam、Vadivel Vaithiyanathan、Kodirajan Selvakumar

  DOI：10.1016/j.tetlet.2008.01.119

  日期：2008.3

  A simple, mild and efficient CAN mediated oxidation of Morita-Baylis-Hillman adducts of 5-methyl-N-alkylisatins 1a-13a to 5-formyl-N-alkylisatins lb-13b under ambient reaction conditions is reported. Simple and isomerized 5-methyl-N-alkylisatin derivatives 1-4 have also been tested and failed to provide the corresponding formylated products. A plausible reaction mechanism has been proposed. (C) 2008 Elsevier Ltd. All rights reserved.