ethyl 2-(1-allyl-3-hydroxy-2-oxoindolin-3-yl)acrylate | 1392206-40-4

• 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: ethyl 2-(1-allyl-3-hydroxy-2-oxoindolin-3-yl)acrylate
• 英文别名: ethyl 2-(1-allyl-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acrylate；Ethyl 2-(3-hydroxy-2-oxo-1-prop-2-enylindol-3-yl)prop-2-enoate
• CAS: 1392206-40-4
• 化学式: C₁₆H₁₇NO₄
• 分子量: 287.315
• InChiKey: MIODIHGTXMLDLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-烯丙基-1H-吲哚-2,3-二酮 、 丙烯酸乙酯 在 BF₄^(1-)*C₉H₁₉N₂O⁽¹⁺⁾ 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 0.4h， 以92%的产率得到ethyl 2-(1-allyl-3-hydroxy-2-oxoindolin-3-yl)acrylate
  参考文献：
  名称：

  Highly Efficient Synthesis of Novel Morita-Baylis-Hillman Adducts from Activated Ketones Using a DABCO-Based Hydroxy Ionic Liquid (HIL) as a Recyclable Catalyst-Solvent

  摘要：

  A highly efficient non-imidazolium DABCO-based ionic liquid has been prepared for the synthesis of biologically active Morita-Baylis-Hillman adducts from activated ketones. The results show that the ionic liquid is very efficient in the Morita-Baylis-Hillman reaction due to its operational simplicity, high yields, dual catalyst-solvent properties, and excellent recyclability and reusability. This hydroxy ionic liquid acts as a protic solvent and tertiary amine for the preparation of biologically active compounds from isatin, ninhydrin, 1,2-acenaphthylenequinone, and benzil with high yields and very short reaction times.

  DOI：

  10.1055/s-0031-1290773

文献信息

• Diisobutylaluminium hydride mediated efficient synthesis of Morita–Baylis–Hilman adducts through α‐functionalization of alkyl propiolates
  作者：Sailam Sri Gogula、Ramakrishna Konakalla、Kamalaker Reddy Kamireddy、Muralidar Reddy Puchakayala、Ch. Abraham Lincoln、Venkata Subba Reddy Basireddy

  DOI：10.1002/jhet.4602

  日期：2023.3

  Generally, oxindole derivatives are biologically important molecules and valuable building blocks in organic synthesis. Herein, we report a diisobutylaluminium hydride mediated efficient one-pot synthesis of oxindole derivatives using N-substituted isatins with methyl or ethyl propiolates at lower temperature (−78°C) through Morita-Baylis-Hillman (MBH) reaction. Within a short reaction time, a wide

  通常，羟吲哚衍生物是生物学上重要的分子和有机合成中有价值的组成部分。在此，我们报道了一种二异丁基氢化铝介导的羟吲哚衍生物的高效一锅法合成，使用N-取代靛红与丙炔酸甲酯或乙酯在较低温度 (-78°C) 下通过 Morita-Baylis-Hillman (MBH) 反应。在较短的反应时间内，可以在温和的反应条件下以优异的产率轻松获得各种N-烷基或N-芳基 3-羟基羟吲哚衍生物（MBH 加合物）。