2-(3-Hydroxy-1,5-dimethyl-2-oxoindol-3-yl)prop-2-enenitrile | 1021359-50-1

• 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: 2-(3-Hydroxy-1,5-dimethyl-2-oxoindol-3-yl)prop-2-enenitrile
• 英文别名: 2-(3-hydroxy-1,5-dimethyl-2-oxoindol-3-yl)prop-2-enenitrile
• CAS: 1021359-50-1
• 化学式: C₁₃H₁₂N₂O₂
• 分子量: 228.25
• InChiKey: PFWJREZVOUHPPN-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：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  64.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-Hydroxy-1,5-dimethyl-2-oxoindol-3-yl)prop-2-enenitrile 在 ammonium cerium(IV) nitrate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 0.08h， 生成 2-(5-formyl-3-hydroxy-1-methyl-2-oxoindolin-3-yl) acrylonitrile
  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

• A short time isomerisation for the synthesis of 3-ylideneoxindoles from Morita-Baylis-Hillman adduct of isatin derivatives with 1-hexyn-3-ol using FeCl3 and K-10 clay
  作者：Vadivel Vaithiyanathan、Ganesan Ravichandran

  DOI：10.1016/j.tetlet.2021.153212

  日期：2021.7

  3-ylideneoxindoles are synthesized from Morita-Baylis-Hillman adduct of isatin derivatives with different alcohols using FeCl3 and K-10 clay under microwave irradiation. The reaction occurs in 3 min. As this work done with the help of FeCl3, K-10 clay and microwave irradiation for short time it is an eco-friendly green synthesis. The details of the work are elaborately discussed in this letter.

  在微波辐射下，使用 FeCl 3和 K-10 粘土，由靛红衍生物与不同醇的 Morita-Baylis-Hillman 加合物合成 3-ylideneoxindole 。反应在 3 分钟内发生。由于这项工作是在 FeCl 3、K-10 粘土和微波辐射的帮助下完成的，因此它是一种环保的绿色合成方法。这封信中详细讨论了这项工作的细节。
• Synthesis of five‐ring‐fused azepinone derivatives from bis‐isatins via sequential 6π‐electrocyclic ring closure, ring expansion, and dehydrogenation process
  作者：Sangku Lee、Junseong Lee、Jae Nyoung Kim

  DOI：10.1002/bkcs.12672

  日期：——

  Five-ring-fused azepinone derivatives were synthesized serendipitously from bis-isatins via sequential 6π-electrocyclic ring closure, ring expansion, and dehydrogenation process in moderate yields (34%–47%). The reaction was carried out in diphenyl ether at 230 °C for 4–12 h under O2 balloon atmosphere.

  通过顺序 6π-电环闭环、扩环和脱氢过程，以中等产率 (34%–47%) 从双靛红偶然合成了五环稠合氮杂庚酮衍生物。反应在二苯醚中于 230 °C 在 O 2气球气氛下进行 4-12 小时。
• 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.