3-hydroxy-1-methyl-3-((6-methylpyridin-2-yl)methyl)indolin-2-one | 1356219-59-4

• 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-((6-methylpyridin-2-yl)methyl)indolin-2-one
• 英文别名: 3-Hydroxy-1-methyl-3-[(6-methylpyridin-2-yl)methyl]indol-2-one；3-hydroxy-1-methyl-3-[(6-methylpyridin-2-yl)methyl]indol-2-one
• CAS: 1356219-59-4
• 化学式: C₁₆H₁₆N₂O₂
• 分子量: 268.315
• InChiKey: RBOZEMIQCLKCOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  53.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,6-二甲基吡啶 、 1-甲基靛红 在 iron(II) acetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以62%的产率得到3-hydroxy-1-methyl-3-((6-methylpyridin-2-yl)methyl)indolin-2-one
  参考文献：
  名称：

  Iron-catalyzed C(sp³)–H functionalization of methyl azaarenes: a green approach to azaarene-substituted α- or β-hydroxy carboxylic derivatives and 2-alkenylazaarenes

  摘要：

  使用铁催化的C(sp³)-H官能团化方法，将甲基氮杂芳烃与羰基化合物反应，合成了目标化合物。

  DOI：

  10.1039/c4ra10939b

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。
• Yb(OTf)3-Catalyzed Addition of 2-Methyl Azaarenes to Isatins via C-H Functionalization
  作者：Rui NIU、Shiying YANG、Jian XIAO、Tao LIANG、Xingwei LI

  DOI：10.1016/s1872-2067(11)60414-2

  日期：2012.9

  this key motif is of vital importance. Yb(OTf)3-catalyzed addition of 2- or 4-methyl azaarenes to isatins via C-H functionalization was developed. Moderate to good yields were obtained for various isatins and azaarenes. This method provides rapid protocol for the synthesis of biologically important azaarene-substituted 3-hydroxy-2-oxindoles in one step. The success of this reaction expands the synthetic

  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。
• Iron-catalyzed C(sp³)–H functionalization of methyl azaarenes: a green approach to azaarene-substituted α- or β-hydroxy carboxylic derivatives and 2-alkenylazaarenes
  作者：Danwei Pi、Kun Jiang、Haifeng Zhou、Yuebo Sui、Yasuhiro Uozumi、Kun Zou

  DOI：10.1039/c4ra10939b

  日期：——

  An iron-catalyzed C(sp³)–H functionalization of methyl azaarenes with carbonyls to access the title compounds have been described.

  使用铁催化的C(sp³)-H官能团化方法，将甲基氮杂芳烃与羰基化合物反应，合成了目标化合物。