3-hydroxy-5-nitro-3-(pyridin-2-ylmethyl)indolin-2-one | 187325-51-5

• 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-5-nitro-3-(pyridin-2-ylmethyl)indolin-2-one
• 英文别名: 3-hydroxy-5-nitro-3-(pyridin-2-ylmethyl)-1H-indol-2-one
• CAS: 187325-51-5
• 化学式: C₁₄H₁₁N₃O₄
• 分子量: 285.259
• InChiKey: BTQDWJZQZDTLIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-hydroxy-5-nitro-3-(pyridin-2-ylmethyl)indolin-2-one 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 24.0h， 以74.8%的产率得到(E)-5-nitro-3-(2-pyridinylmethylidene)-2-oxindole
  参考文献：
  名称：

  具有基本功能的吲哚的化学，第 31 部分 Spiro [cyclopropane-1,3 ' [3H] indole] -2 ' (1'H) -ones 的合成具有抗缺氧作用

  摘要：

  羟基吲哚酮 (1-6, 15-16) 通过用 4-甲苯磺酸脱水转化为靛红 (7,9-13, 17-19)。在少数情况下也分离出二聚体型化合物 (14, 20)。将获得的靛红转化为 3-螺-环丙烷-羟吲哚（21-32）与二甲基氧锍甲基化物。化合物 22 显示出对低压缺氧和三乙基锡诱导的脑水肿的保护作用。

  DOI：

  10.1002/ardp.19963291206
• 作为产物：
  描述：

  碳酸甲丙酯 、 5-硝基靛红 在 碘 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 以70%的产率得到3-hydroxy-5-nitro-3-(pyridin-2-ylmethyl)indolin-2-one
  参考文献：
  名称：

  碘催化通过sp 3 C–H官能团有效合成氮杂芳烃取代的3-羟基-2-氧吲哚衍生物

  摘要：

  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。

  DOI：

  10.1016/j.tet.2012.07.051

文献信息

• 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。
• Enhanced catalytic performance of magnetic Fe3O4–MnO2 nanocomposites for the decolorization of rhodamine B, reduction of 4-nitroaniline, and sp3 C–H functionalization of 2-methylpyridines to isatins
  作者：Kanchan Mishra、Tej Narayan Poudel、Nagaraj Basavegowda、Yong Rok Lee

  DOI：10.1016/j.jcat.2016.09.020

  日期：2016.12

  A novel biosynthesized nanocatalyst, iron oxide-loaded manganese dioxide nanocomposites (Fe3O4-MnO2 NCs), was fabricated with the aid of a Perilla frutescens leaf extract. The MnO2 is composed of numerous nanoflakes radiating from the center, which results to a flowerlike structure. A change in the flowerlike morphology of MnO2 in Fe3O4-MnO2 NCs was observed due to the distribution of Fe3O4 nanoparticles on the surface of MnO2. To check the catalytic performance of the synthesized NCs, they were utilized as a catalyst for the decolorization of rhodamine B (RhB), reduction of 4-nitroaniline (4-NA), and spa C-H functionalization of 2-methylpyridines to isatins for the-synthesis of azaarene-substituted 3-hydroxy-2-oxindole derivatives. The Fe3O4-loaded MnO2 exhibited enhanced catalytic ability over MnO2. Moreover, the nanocomposites could be recovered by a magnetic separation technique and reused for five consecutive reactions without significant loss of catalytic ability. (C) 2016 Elsevier Inc. All rights reserved.
• Preparation of aryl-substituted 2-oxyindoles by superelectrophilic chemistry
  作者：Rajasekhar Reddy Naredla、Erum K. Raja、Douglas A. Klumpp

  DOI：10.1016/j.tetlet.2013.04.011

  日期：2013.6

  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.
• Chemistry of Indoles Carrying a Basic Function, Part 31 Synthesis of Spiro[cyclopropane-1,3′[3H]indol]-2′(1′H)-ones with Antihypoxic Effects
  作者：István Moldvai、Eszter Gács-Baitz、Mihály Balázs、Mária Incze、Csaba Szántay

  DOI：10.1002/ardp.19963291206

  日期：——

  into isatinylidenes (7,9–13, 17–19) by dehydration with 4‐toluenesulfonic acid. The dimer‐type compounds (14, 20) were also isolated in a few cases. The obtained isatinylidenes were transformed into 3‐spiro‐cyclopropane‐oxindoles (21–32) with dimethyloxosulfonium methylide. Compound 22 shows protective effects against hypobaric hypoxia and triethyltin induced brain edema.

  羟基吲哚酮 (1-6, 15-16) 通过用 4-甲苯磺酸脱水转化为靛红 (7,9-13, 17-19)。在少数情况下也分离出二聚体型化合物 (14, 20)。将获得的靛红转化为 3-螺-环丙烷-羟吲哚（21-32）与二甲基氧锍甲基化物。化合物 22 显示出对低压缺氧和三乙基锡诱导的脑水肿的保护作用。
• 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。