2-((3-chlorophenyl)(2-methyl-1H-indol-3-yl)methyl)malononitrile | 1306680-25-0

• 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: 2-((3-chlorophenyl)(2-methyl-1H-indol-3-yl)methyl)malononitrile
• 英文别名: 2-[(3-chlorophenyl)-(2-methyl-1H-indol-3-yl)methyl]propanedinitrile
• CAS: 1306680-25-0
• 化学式: C₁₉H₁₄ClN₃
• 分子量: 319.793
• InChiKey: ZUEJNYWAHNSBOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  63.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-氯苯甲醛 在 choline chloride - 1,3-dimethylurea deep-eutectic salt 作用下， 以 乙醇 、 水 为溶剂， 反应 36.17h， 生成 2-((3-chlorophenyl)(2-methyl-1H-indol-3-yl)methyl)malononitrile
  参考文献：
  名称：

  Water Assisted and Choline Chloride-Dimethylurea Deep Eutectic Salts as Catalyst towards the Attractive Reaction of Indole, Benzaldehyde, and Malononitrile

  摘要：

  The condensation of indole, benzaldehyde, and malononitrile was relatively rigorous compared with other Yonemitsu type reaction. We described a strategy using catalytic amount of choline chloride-dimethylurea deep eutectic salts as cheap and safe accelerator. We also found that introducing right amount of water in reaction system was crucial. This method tolerates variations in all three components to get desired 3-substituted indoles in satisfactory yields.

  DOI：

  10.3987/com-18-13913

文献信息

• An efficient and clean Michael addition of indoles to electron-deficient olefins under solvent- and catalyst-free condition
  作者：Xiong-Li Liu、Dong Xue、Zun-Ting Zhang

  DOI：10.1002/jhet.569

  日期：2011.3

  An efficient Michael addition of indoles to electron‐deficient olefins under solvent‐ and catalyst‐free condition afforded biologically important 3‐substituted indole derivatives in good to excellent yields was reported. The acidic NH proton of indole plays a key role in Michael addition of indoles to electron‐deficient olefins. This very simple procedure provides an efficient and clean process for

  据报道，在无溶剂和无催化剂的条件下，将吲哚高效迈克尔加成到缺电子的烯烃中，可得到生物学上重要的3-取代的吲哚衍生物，收率良好至极佳。吲哚的酸性NH质子在吲哚向缺乏电子的烯烃的迈克尔加成反应中起关键作用。这个非常简单的过程为吲哚衍生物的合成提供了一种有效而清洁的方法。J.杂环化​​学。（2011）。
• Polyethylene glycol (PEG-200)-promoted sustainable one-pot three-component synthesis of 3-indole derivatives in water
  作者：Leilei Wang、Manna Huang、Xinhai Zhu、Yiqian Wan

  DOI：10.1016/j.apcata.2012.12.008

  日期：2013.3

  A sustainable three-component reaction of indoles, aldehydes, and malononitrile in water promoted by polyethylene glycol (PEG-200) afforded 3-indole derivatives in good to excellent yields.

  聚乙二醇（PEG-200）促进了水中吲哚，醛和丙二腈的可持续三组分反应，得到了3-吲哚衍生物，收率良好。