5-chloro-3-hydroxy-3-(2-oxo-2-(p-tolyl)ethyl)indolin-2-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-chloro-3-hydroxy-3-(2-oxo-2-(p-tolyl)ethyl)indolin-2-one
• 英文别名: 5-chloro-3-hydroxy-3-[2-(4-methylphenyl)-2-oxoethyl]-1,3-dihydro-2H-indol-2-one；5-chloro-3-hydroxy-3-[2-(4-methylphenyl)-2-oxoethyl]-1H-indol-2-one
• 化学式: C₁₇H₁₄ClNO₃
• 分子量: 315.756
• InChiKey: WZMNWHFPHJNGEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-chloro-3-hydroxy-3-(2-oxo-2-(p-tolyl)ethyl)indolin-2-one 在 盐酸 、 4-氟苯乙酮 作用下， 生成
  参考文献：
  名称：

  tert‐Butyl Nitrite Promoted Visible‐Light‐Induced Steric‐Hindrance‐Regulated Concurrent Cross‐Coupling and Regioselective Nitration of 3‐Alkylidene‐2‐oxindoles

  摘要：

  A tert‐butyl nitrite (TBN) promoted visible‐light‐induced one‐pot C−N cross coupling reaction of 3‐alkylidene‐2‐oxindoles with benzene‐1,2‐diamine was explored. Simultaneously, the indoline motif of 3‐alkylidene‐2‐oxindoles as well as 3‐ylidene oxindoles are regioselectively nitrated at the C‐6 position by in‐situ formed NO₂ radical. (E)‐3‐(2‐(aryl)‐2‐oxoethylidene)oxindole and (E)‐3‐ylidene oxindole produce distinct nitrated diastereomeric coupling products, a phenomenon influenced by the steric bulk of the functional group. The experimental findings suggest the potential involvement of a radical pathway in this reaction.

  DOI：

  10.1002/adsc.202301159
• 作为产物：
  描述：

  5-氯靛红 、 对甲基苯乙酮 在 1,3,5-triazine-piperazine immobilised mesoporous silica 作用下， 以 四氢呋喃 为溶剂， 反应 192.0h， 以80%的产率得到5-chloro-3-hydroxy-3-(2-oxo-2-(p-tolyl)ethyl)indolin-2-one
  参考文献：
  名称：

  Ordered short channel mesoporous silica modified with 1,3,5-triazine–piperazine as a versatile recyclable basic catalyst for cross-aldol, Knoevenagel and conjugate addition reactions with isatins

  摘要：

  一种可回收的三嗪-哌嗪固定在硅胶支撑材料上的材料被探索作为在室温下从异吲哚酮合成的杂环骨架的非均相催化剂。

  DOI：

  10.1039/c5ra00406c

文献信息

• DABCO-catalyzed synthesis of 3-substituted-3-hydroxyindolin-2-ones in aqueous media
  作者：Keshri Nath Tiwari、Darshana Bora、Garima Chauhan、Deepika Yadav、Kavita Sharma、Ashima Thakur、Lachhman Singh、Vishwadeep Tripathi

  DOI：10.1080/00397911.2016.1160411

  日期：2016.4.2

  ABSTRACT An efficient and greener protocol for easy access to 3-susbstituted-3-hydroxy-2-oxindoles by the reaction with various substituted isatins and acetophenones is described. This protocol is widely applicable for a variety of isatins and acetophenones using water as a reaction media and 1,4-diazabicyclo[2.2.2]octane (DABCO) as catalyst with shorter reaction time and good to excellent yield of

  摘要描述了一种通过与各种取代的靛红和苯乙酮反应轻松获得 3-取代-3-羟基-2-oxindoles 的有效和更环保的协议。该方案广泛适用于以水为反应介质和 1,4-二氮杂双环 [2.2.2] 辛烷 (DABCO) 为催化剂的各种靛红和苯乙酮，具有较短的反应时间和良好的产品收率。图形概要
• Oxidative ring expansion of 3-hydroxy-3-phenacyloxindoles using phenyliodine diacetate and molecular iodine: Synthesis of 2-hydroxy-2-aryl/alkyl-2,3-dihydroquinolin-4(1H)-ones
  作者：Ashish C. Kavale、Amit H. Kalbandhe、Imran A. Opai、Atul A. Jichkar、Nandkishor N. Karade

  DOI：10.1016/j.tetlet.2020.152631

  日期：2021.1

  Oxidation of tertiary alcohol of the type 3-hydroxy-3-phenacyloxindoles using the combination of phenyliodine diacetate and molecular iodine in methanol results in oxidative cleavage of C2-C3 bond to form isocyanate as an intermediate with its subsequent trapping by methanol to form ortho-carbamates of 1,3-diaryl carbonyl compounds which further undergoes concurrent cyclization to furnish 2-hydroxy-2-aryl/alkyl-2

  使用苯乙酸二乙酸酯和分子碘在甲醇中对3-羟基-3-苯并氧杂吲哚类的叔醇进行氧化会导致C2-C3键的氧化裂解，形成异氰酸酯作为中间体，随后被甲醇捕获而形成邻位- 1,3-二芳基羰基化合物的氨基甲酸酯，进一步进行同时环化，以高收率提供2-羟基-2-芳基/烷基-2,3-二氢喹啉-4（1 H）-ones衍生物。
• An efficient and direct synthesis of substituted 2-phenylquinoline-4-carboxamides from 3-substituted-3-hydroxyindolin-2-ones
  作者：Keshri Nath Tiwari、Rinku Choubey、Saumya Shukla、Parul Gautam

  DOI：10.24820/ark.5550190.p009.760

  日期：——

  A simple and direct synthesis of substituted 2-phenylquinoline-4-carboxamides from 3-substituted-3hydroxyindolines in presence of ammonium acetate is described. The developed protocol also allows synthesis of the carboxamide moeity directly from isatin and acetophenone in one pot under optimized conditions. The protocol has the merits of simple reaction conditions, easy work up process and good yields

  描述了在乙酸铵存在下从 3-取代-3-羟基二氢吲哚中简单直接合成取代的 2-苯基喹啉-4-甲酰胺。开发的协议还允许在优化条件下在一锅中直接从靛红和苯乙酮合成羧酰胺部分。该方案具有反应条件简单、后处理容易、产品收率高等优点。
• Ordered short channel mesoporous silica modified with 1,3,5-triazine–piperazine as a versatile recyclable basic catalyst for cross-aldol, Knoevenagel and conjugate addition reactions with isatins
  作者：Naveen Gupta、Tamal Roy、Debashis Ghosh、Sayed H. R. Abdi、Rukhsana I. Kureshy、Noor-ul H. Khan、Hari C. Bajaj

  DOI：10.1039/c5ra00406c

  日期：——

  A recyclable triazine–piperazine immobilized silica supported material was explored as a heterogeneous catalyst for indole skeletal synthesized from isatins at RT.

  一种可回收的三嗪-哌嗪固定在硅胶支撑材料上的材料被探索作为在室温下从异吲哚酮合成的杂环骨架的非均相催化剂。
• Design, synthesis and insilico studies of 3-fluoro-3-substituted oxindoles against cancer targets
  作者：P.L.N. Ranganath、A. Venkat Narsaiah

  DOI：10.1016/j.jfluchem.2023.110134

  日期：2023.5

  substituted isatins were subjected to Aldol condensation with various ketones. The resulted 3-hydroxy compounds were transformed into fluorine derivatives. Thus obtained, 3-fluoro-3-substituted oxindoles were screened for Insilco evaluation against anti-cancer targets VEGFR2 and GSK-3β. The study reveals that the fluoro compounds showed binding at their active sites. Particularly, compounds 4i, 4n and

  靛红和取代的靛红经过与各种酮的羟醛缩合。将所得的 3-羟基化合物转化为氟衍生物。由此获得的 3-fluoro-3-substituted oxindoles 被筛选用于针对抗癌靶标 VEGFR2 和 GSK-3β 的 Insilco 评估。该研究表明，氟化合物在其活性位点显示出结合。特别是，化合物4i、4n和4q显示出最好的结合亲和力和与它们各自的共结晶配体相似的疏水相互作用。