3-hydroxy-1-methyl-3-(pyridin-2-ylmethyl)indolin-2-one | 882750-63-2

• 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: 3-hydroxy-1-methyl-3-(pyridin-2-ylmethyl)indolin-2-one
• 英文别名: 3-Hydroxy-1-methyl-3-(pyridin-2-ylmethyl)indol-2-one
• CAS: 882750-63-2
• 化学式: C₁₅H₁₄N₂O₂
• 分子量: 254.288
• InChiKey: XULJCIFLVWEFHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  53.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxy-1-methyl-3-(pyridin-2-ylmethyl)indolin-2-one 、 苯 在 三氟甲磺酸 作用下， 反应 2.0h， 以81%的产率得到1-methyl-3-phenyl-3-(pyridin-2-ylmethyl)indolin-2-one
  参考文献：
  名称：

  Preparation of aryl-substituted 2-oxyindoles by superelectrophilic chemistry

  摘要：

  A series of pyridyl-substituted 3-hydroxy-2-oxyindoles have been prepared and reacted with arenes in superacid promoted Friedel-Crafts reactions. The product aryl-substituted 2-oxyindoles are formed in generally good yields. With substituted arenes such as toluene, bromobenzene, or ethyl salicylate, the Friedel-Crafts reactions occur with excellent regioselectivity. A mechanism is proposed involving dicationic, superelectrophilic species leading to the electrophilic aromatic substitution chemistry. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.04.011
• 作为产物：
  描述：

  碳酸甲丙酯 、 1-甲基靛红 在 ytterbium(III) triflate 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以39%的产率得到3-hydroxy-1-methyl-3-(pyridin-2-ylmethyl)indolin-2-one
  参考文献：
  名称：

  Yb(OTf)3-催化通过 CH 官能化将 2-甲基氮杂芳烃加成到靛红

  摘要：

  摘要 3-取代-3-羟基-2-羟吲哚富含一系列具有生物活性的天然产物和药物，开发构建这一关键基序的有效方法至关重要。开发了 Yb(OTf)3 催化通过 CH 官能化将 2-或 4-甲基氮杂芳烃加成到靛红。各种靛红和氮杂芳烃获得了中等至良好的产量。该方法为一步合成具有生物学意义的氮杂芳烃取代的 3-羟基-2-羟吲哚提供了快速方案。该反应的成功扩大了路易斯酸在有机合成中 sp3 CH 键催化功能化中的合成效用。

  DOI：

  10.1016/s1872-2067(11)60414-2

文献信息

• A novel and efficient synthesis of azaarene-substituted 3-hydroxy-2-oxindoles via sp3 C–H functionalization of 2-methyl azaarenes and (2-azaaryl)methanes over a heterogeneous, reusable silica-supported dodecatungstophosphoric acid catalyst
  作者：Shafeek A. R. Mulla、Mohsinkhan Y. Pathan、Santosh S. Chavan

  DOI：10.1039/c3ra43515f

  日期：——

  A novel and efficient protocol has been developed for the synthesis of azaarene-substituted 3-hydroxy-2-oxindoles via sp3 C–H functionalization of 2-methyl azaarenes and (2-azaaryl)methanes with isatin in good to excellent yield. This is the first example in which heterogeneous, reusable silica supported dodecatungstophosphoric acid (DTP/SiO2) catalyzed sp3 C–H functionalization of 2-substituted azaarenes and (2-azaaryl)methanes.

  开发了一种新颖且高效的方法，通过2-甲基吖嗪和(2-吖基苯基)甲烷在异钨酸硅（DTP/SiO2）催化下进行的sp3 C―H官能团化反应，合成取代的3-羟基-2-氧吲哚。此方法在良好至优异的产率下进行。这是首个实例，展示了可重复使用的非均相硅载体十二钨磷酸（DTP/SiO2）催化2-取代吖嗪和(2-吖基苯基)甲烷的sp3 C―H官能团化反应。
• Facile Synthesis of Azaarene-Substituted 3-Hydroxy-2-oxindoles via Brønsted Acid Catalyzed sp³ C–H Functionalization
  作者：Rui Niu、Jian Xiao、Tao Liang、Xingwei Li

  DOI：10.1021/ol2030982

  日期：2012.2.3

  Brønsted acid catalyzed functionalization of sp3 C–H bonds in 2-methyl azaarenes has been achieved in the reaction with isatins. This method provides facile synthesis of biologically important azaarene-substituted 3-hydroxy-2-oxindoles in one step in moderate to good yields.

  通过与靛红的反应，布朗斯台德酸催化了2-甲基氮杂芳烃中sp 3 C–H键的官能化。该方法以中等至良好的收率一步地提供了生物学上重要的氮杂芳烃取代的3-羟基-2-氧吲哚的容易的合成。
• Iodine-catalyzed efficient synthesis of azaarene substituted 3-hydroxy-2-oxindole derivatives through sp3 C–H functionalization
  作者：Srinivasu V.N. Vuppalapati、Yong Rok Lee

  DOI：10.1016/j.tet.2012.07.051

  日期：2012.9

  Iodine-catalyzed benzylic sp3 C–H bond functionalization of lutidines or picolines to isatins is described. This synthetic method provides a rapid entry towards biologically interesting 3-azaarene substituted 3-hydroxy-2-oxindole derivatives.

  本文描述了由碘催化的二甲基吡啶或甲基吡啶对靛红的苄基sp 3 C–H键官能化。这种合成方法提供了快速进入生物学上令人感兴趣的3-氮杂芳烃取代的3-羟基-2-氧吲哚衍生物的途径。
• A simple and sustainable tetrabutylammonium fluoride (TBAF)-catalyzed synthesis of azaarene-substituted 3-hydroxy-2-oxindoles through sp³ C–H functionalization
  作者：Kumkum Kumari、Bharat Kumar Allam、Krishna Nand Singh

  DOI：10.1039/c3ra47332e

  日期：——

  A green, practical, and metal-free protocol for direct addition of α-and γ-alkylazaarenes to isatins has been developed via sp3 C–H functionalization in water under controlled microwave radiation. This methodology provides a mild and fast route to biologically important azaarene-substituted 3-hydroxy-2-oxindoles in good to excellent yields.

  通过在受控的微波辐射下，通过sp 3 C–H在水中的官能化，开发了一种绿色，实用且无金属的方案，用于将α-和γ-烷基氮杂氮烯直接添加到靛红中。该方法提供了温和而快速的途径，以良好至极佳的产率获得了生物学上重要的氮杂芳烃取代的3-羟基-2-氧吲哚。
• β-Cyclodextrin catalysed C–C bond formation via C(sp³)–H functionalization of 2-methyl azaarenes with diones in aqueous medium
  作者：Atul Kumar、Ratnakar Dutt Shukla

  DOI：10.1039/c4gc02287d

  日期：——

  β-Cyclodextrin catalysed C(sp³)–H functionalization of 2-alkyl-azaarenes with homocyclic as well as heterocyclic diones in water has been developed. This biomimetic catalyst oriented methodology provides a sustainable protocol for C–H functionalization, an area mainly dominated by transition metals.

  β-环糊精在水中催化2-烷基-氮杂芳烃与同环和异环二酮的C(sp3)–H官能化反应已经被开发出来。这种生物模仿催化剂定向方法为C–H官能化提供了可持续的方案，这个领域主要由过渡金属主导。