naphthalen-2-yl 2-(1-allyl-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acrylate | 1392206-59-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: naphthalen-2-yl 2-(1-allyl-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acrylate
• 英文别名: Naphthalen-2-yl 2-(3-hydroxy-2-oxo-1-prop-2-enylindol-3-yl)prop-2-enoate
• CAS: 1392206-59-5
• 化学式: C₂₄H₁₉NO₄
• 分子量: 385.419
• InChiKey: ZPWFFFXYYJKDHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 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 、 2-萘基丙烯酸酯 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 0.38h， 以83%的产率得到naphthalen-2-yl 2-(1-allyl-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-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