3-Ethyl-3-hydroxy-1-methyl-1,3-dihydroindol-2-one | 61110-64-3

• 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-Ethyl-3-hydroxy-1-methyl-1,3-dihydroindol-2-one
• 英文别名: 3-ethyl-3-hydroxy-1-methylindolin-2-one；2H-Indol-2-one, 3-ethyl-1,3-dihydro-3-hydroxy-1-methyl-；3-ethyl-3-hydroxy-1-methylindol-2-one
• CAS: 61110-64-3
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: UJXQMZYRKZTGJC-UHFFFAOYSA-N

物化性质

• 熔点：
  181-182 °C
• 沸点：
  412.4±45.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Ethyl-3-hydroxy-1-methyl-1,3-dihydroindol-2-one 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 3-chloro-3-ethyl-1-methylindolin-2-one
  参考文献：
  名称：

  3-Halooxindole通过可见光光催化的同质耦合：轻度访问3,3'-Bioxindoles。

  摘要：

  本文介绍了一种简单的方法来光催化诱导的卤化三元的均相偶联。该方法具有温和的反应条件，出色的官能团耐受性，高收率，低的光催化剂负载量以及成功应用于高度空间受限的体系的特点。根据反应结果，提出了一种新的稳定自由基诱导的均偶联反应机理。

  DOI：

  10.1021/acs.joc.6b01045
• 作为产物：
  描述：

  N-甲基-2-氧代-N-苯基丁酰胺 在 三氟乙酸 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以94%的产率得到3-Ethyl-3-hydroxy-1-methyl-1,3-dihydroindol-2-one
  参考文献：
  名称：

  Trifluoroacetic Acid-Promoted Synthesis of 3-Hydroxy, 3-Amino and Spirooxindoles from α-Keto-N-Anilides

  摘要：

  Ketoanilides containing alkyl side chains were readily cyclized to 3-hydroxy-2-oxindoles or spirooxindoles by a single or double intramolecular Friedel-Crafts reaction in the presence of trifluoroacetic acid (TFA) at room temperature or at 45 degrees C. alpha-Iminocarboxamides, generated in situ from ketoamides, cyclized similarly to 3-aminooxindoles under identical conditions,

  DOI：

  10.1021/ol202263a

文献信息

• Cross-Dehydrogenative Cyclization–Dimerization Cascade Sequence for the Synthesis of Symmetrical 3,3′-Bisoxindoles
  作者：Farhaan Dobah、C. Munashe Mazodze、Wade F. Petersen

  DOI：10.1021/acs.orglett.1c01799

  日期：2021.7.16

  The synthesis of symmetrical 3,3′-bisoxindoles from simple acyclic β-oxoanilides is reported. The described method forges three new C–C bonds in a single step via a sequential Mn(OAc)3·2H2O mediated oxidative radical cyclization-fragmentation–dimerization process. The scope of this reaction is demonstrated in the preparation of a variety of 3,3′-bisoxindoles, as well as its application toward the formal

  报道了从简单的无环 β-氧代苯胺合成对称的 3,3'-双氧代吲哚。所描述的方法通过连续的 Mn(OAc) 3 · 2H 2 O 介导的氧化自由基环化-断裂-二聚化过程在一个步骤中形成三个新的 C-C 键。该反应的范围体现在各种 3,3'-双氧吲哚的制备中，以及其在花萼科生物碱 (±)-叶蓍碱的正式合成中的应用。
• Autocatalytic synthesis of 3-ethyl-3-hydroxy-indole-2-ones and their neuroprotection and antitumor activities' evaluation
  作者：Gang Chen、Jiao Lin、Jie Zhang、Ya Wu、Xuefan Gu、Xiaojiang Hao、Yu Zhang

  DOI：10.1016/j.crci.2018.02.009

  日期：2018.5

  Résumé In this study, a series of 3-ethyl-3-hydroxy-indole-2-ones were synthesized through the addition reaction of Et2Zn and N-substituted isatin by an autocatalytic process. The synthesized compounds were characterized by NMR spectroscopy and mass spectrometry, and the reaction mechanism was discussed. The antitumor and neuroprotection activities of these compounds were evaluated. The results showed that several compounds display protection activity on H2O2-induced apoptosis of PC12 cells, which are more effective than that of (±)-α-tocopherol Vitamin E (VE). Moreover, these compounds also show antitumor activity against A549 and P388 cell lines.

  摘要 本研究通过Et2Zn与N-取代靛红的加成反应，在自催化过程中合成了一系列3-乙基-3-羟基-吲哚-2-酮。通过核磁共振波谱和质谱对合成的化合物进行了表征，并讨论了反应机理。对这些化合物的抗肿瘤和神经保护活性进行了评估。结果表明，几种化合物对 H2O2 诱导的 PC12 细胞凋亡具有保护活性，其效果优于(±)-α-生育酚维生素 E（VE）。此外，这些化合物还显示出对 A549 和 P388 细胞株的抗肿瘤活性。
• Photoredox-catalyzed radical–radical cross coupling of ketyl radicals with unstabilized primary alkyl radicals
  作者：Shishen Feng、Hong Liu、Yan Li、Yewen Fang

  DOI：10.1039/d4cc00620h

  日期：2024.4.18

  sterically hindered alcohols has been successfully developed via radical–radical coupling reactions enabled by mild and redox-neutral photocatalysis. With alkylsilicates as the radical precursors, a range of primary alkyl radicals bearing various functional groups could couple with a range of phthalimides and activated ketones.

  在此，通过温和和氧化还原中性光催化实现的自由基-自由基偶联反应，成功开发了一种处理空间位阻醇制备的新方案。使用烷基硅酸酯作为自由基前体，一系列带有各种官能团的伯烷基可以与一系列邻苯二甲酰亚胺和活化酮偶联。
• Catalyst-free synthesis of 3-hydroxy-3-(alkyl/aryl)indolin-2-ones by addition of organoaluminum reagents to isatins
  作者：G. Santosh Kumar、Palakuri Ramesh、A. Sanjeeva Kumar、A. Swetha、H.M. Meshram

  DOI：10.1016/j.tetlet.2013.07.027

  日期：2013.9

  An efficient synthesis of 3-hydroxy-3-(alkyl/aryl)indol-2-one derivatives has been described by the reactions of isatin with organoaluminum reagents. The reaction is very rapid and yields are high. The protocol is applicable for substituted isatins as well as a variety of organoaluminums. (C) 2013 Elsevier Ltd. All rights reserved.
• Balk-Bindseil, Wiebke; Helmke, Elisabeth; Weyland, Horst, Liebigs Annalen, 1995, # 7, p. 1291 - 1294
  作者：Balk-Bindseil, Wiebke、Helmke, Elisabeth、Weyland, Horst、Laatsch, Hartmut

  DOI：——

  日期：——