ethyl 3-hydroxy-1-methyl-2-oxoindoline-3-carboxylate | 201665-52-3

• 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: ethyl 3-hydroxy-1-methyl-2-oxoindoline-3-carboxylate
• 英文别名: Ethyl 3-hydroxy-1-methyl-2-oxoindole-3-carboxylate
• CAS: 201665-52-3
• 化学式: C₁₂H₁₃NO₄
• 分子量: 235.24
• InChiKey: ZQYIHWXDHGUVMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-hydroxy-1-methyl-2-oxoindoline-3-carboxylate 、 alkaline earth salt of/the/ methylsulfuric acid 生成 1-甲基靛红
  参考文献：
  名称：

  Guyot; Martinet, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1913, vol. 156, p. 1627

  摘要：

  DOI：
• 作为产物：
  描述：

  N-甲基苯胺 在 N,N'-二环己基碳二亚胺 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 二氯甲烷 、 2,2,2-三氟乙醇 为溶剂， 反应 1.0h， 生成 ethyl 3-hydroxy-1-methyl-2-oxoindoline-3-carboxylate
  参考文献：
  名称：

  Phenyliodine Bis(trifluoroacetate)-Mediated Oxidative C–C Bond Formation: Synthesis of 3-Hydroxy-2-oxindoles and Spirooxindoles from Anilides

  摘要：

  The reaction of phenyliodine bis(trifluoroacetate) (PIFA) with a series of anilides 1 (E = CO2Et) In CF3CH2OH was found to give 3-hydroxy-2-oxindole derivatives 2, while that with various anilides 1' (E = CON(R-4)Ar) afforded the C-2-symmetric or unsymmetric spirooxindoles 3. These processes feature a metal-free oxidative C(sp(2))-C(sp(3)) bond formation, followed by oxidative hydroxylation or spirocyclization.

  DOI：

  10.1021/ol300418h

文献信息

• Phototandem Catalysis: Efficient Synthesis of 3-Ester-3-hydroxy-2-oxindoles by a Visible Light-Induced Cyclization of Diazoamides through an Aerobic Oxidation Sequence
  作者：Xu-Dong Xia、Yan-Liang Ren、Jia-Rong Chen、Xing-Long Yu、Liang-Qiu Lu、You-Quan Zou、Jian Wan、Wen-Jing Xiao

  DOI：10.1002/asia.201402990

  日期：2015.1

  An unprecedented phototandem catalysis based on a single iridium photocatalyst has been successfully developed. This powerful strategy consists of two mechanistically distinct catalytic cycles, namely, photocatalytic energy transfer (ET) and single electron transfer (SET). The novel protocol allows a rapid and efficient construction of biologically and synthetically important 3‐ester‐3‐hydroxy‐2‐oxindole

  已经成功开发了基于单一铱光催化剂的前所未有的光串联催化。这种强大的策略包括两个机械上截然不同的催化循环，即光催化能量转移（ET）和单电子转移（SET）。新颖的方案允许在非常温和的条件下，通过环化/有氧氧化序列，从容易获得的重氮酰胺快速高效地构建生物学上和合成上重要的3-酯-3-羟基-2-吲哚衍生物。
• Visible light mediated aerobic oxidative hydroxylation of 2-oxindole-3-carboxylate esters: an alternative approach to 3-hydroxy-2-oxindoles
  作者：Jinge Wang、Siyitemer Osman、Xinjiang Lu、Junyi Chen、Xu-Dong Xia

  DOI：10.1515/hc-2019-0114

  日期：2020.11.26

  A convenient aerobic oxidative hydroxylation of 3-substituted oxindoles under mild reaction conditions is described herein. This process was accomplished by the activation of molecular oxygen in the air in the presence of a photocatalyst under the irradiation of visible light. The desired product was delivered in up to 89% yield without the addition of base or stoichiometric oxidant.

  本文描述了一种便利的氧化氢化合成3-取代吲哚酮的方法，在温和的反应条件下完成。该过程通过在可见光照射下在光催化剂的存在下激活空气中的分子氧来实现。所需产物的产率高达89％，无需添加碱或化学氧化剂。

• Palladium-Catalyzed Reactions of Indolic Triflate with Allylic Alcohols
  作者：Béatrice Malapel-Andrieu、Jean-Yves Mérour

  DOI：10.1016/s0040-4039(97)10564-0

  日期：1998.1

  Reactions of 3-indolic triflate 2a with allylic alcohols in presence of palladium (II) acetate gave access to aldehydic compounds and in a more surprising way to C-2 substituted products and oxindole derivatives. © 1997 Elsevier Science Ltd. All rights reserved.

  在乙酸钯（II）的存在下3-吲哚三氟甲磺酸酯2a与烯丙基醇的反应得到醛化合物，并且以更令人惊奇的方式得到C -2取代的产物和羟吲哚衍生物。©1997 Elsevier ScienceLtd。保留所有权利。
• Synthesis and reactivity of substituted 3-([(Trifluoromethyl)sulfonyl]oxy)-1H-indole-2-carboxylate in palladium-catalyzed reactions
  作者：Béatrice Malapel-Andrieu、Jean-Yves Mérour

  DOI：10.1016/s0040-4020(98)00649-8

  日期：1998.9

  Palladium-catalysed Suzuki and Stille reactions of substituted 3-indolyltriflate afforded the corresponding 3-substituted indoles. By contrast, the Heck reaction of allyl alcohol with such triflates gave 2-allyloxy-3-oxoindole derivatives rather than the 3-substituted indole products as a result of a nucleophilic attack on an acyliminium intermediate. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Martinet, Annales de Chimie (Cachan, France), 1919, vol. <9> 11, p. 119
  作者：Martinet

  DOI：——

  日期：——