2-(1-(3-chlorophenyl)propylidene)malononitrile | 1162678-13-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(1-(3-chlorophenyl)propylidene)malononitrile
• 英文别名: 2-[1-(3-Chlorophenyl)propylidene]propanedinitrile
• CAS: 1162678-13-8
• 化学式: C₁₂H₉ClN₂
• 分子量: 216.67
• InChiKey: CXWNXAHTBRNZLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(1-(3-chlorophenyl)propylidene)malononitrile 、 β-硝基苯乙烯 在 [BmIm]OH 、 air 作用下， 以 乙醇 为溶剂， 反应 5.5h， 以64%的产率得到2-Amino-5-methyl-4-phenyl-6-(m-chloro-phenyl)-3-nitrobenzonitrile
  参考文献：
  名称：

  Basic Ionic Liquid as Catalyst for the Efficient and Green Synthesis of 2-Amino-3-nitrobenzonitriles in Ethanol

  摘要：

  [image omitted] A basic ionic liquid, [BmIm]OH was used as catalyst in the cyclocondensation of various kinds of vinylmalononitriles with nitroolefins in ethanol at reflux. A series of 2-amino-3-nitrobenzonitriles were obtained in reasonable yields. The straightforward and green protocol was found to be fairly efficient, and the catalyst could be recycled and reused in subsequent reactions with consistent activity. The mechanism of the reaction was discussed.

  DOI：

  10.1080/00397911.2010.486503

文献信息

• Vinylogous Annulation Cascade Toward Stereoselective Synthesis of Highly Functionalized Indanone Derivatives
  作者：Vinod Bhajammanavar、Sumitava Mallik、Mahiuddin Baidya

  DOI：10.1002/adsc.201900860

  日期：2019.12.3

  been devised to furnish densely functionalized 3‐hydroxyindanone scaffolds in high yields with excellent diastereoselectivity. Unlike preceding approaches that account for the formation of the pentanoid ring, this strategy features construction of the aromatic ring. The protocol is scalable, displays very broad substrates scope including late‐stage functionalization of bioactive estrone, applicable

  已设计出碱促进的亚烷基丙二腈与环戊烯-1,3-二酮的乙烯基级联反应，以及随后的还原顺序，以高产率提供具有出色的非对映选择性的致密官能化的3-羟基茚满酮骨架。与前述解决戊二烯环形成的方法不同，该策略的特征在于芳香环的构建。该协议是可扩展的，显示了非常广泛的底物范围，包括生物活性雌酮的后期功能化，适用于活化的香豆素系统，并且适合于使用茚并喹啉衍生物。
• Efficient and Green Method for the Synthesis of Highly Substituted Cyclohexadiene Derivatives in Aqueous Media
  作者：Xiang-Shan Wang、Jie Zhou、Ke Yang、Mei-Mei Zhang

  DOI：10.1080/00397910903040237

  日期：2010.3.12

  2-amino-6-(3-chlorophenyl)-5-methyl-4-arylcyclohexa-1,5-diene-1,3,3-tricarbonitrile derivatives. The structure of 4e was further confirmed by x-ray diffraction. This three-component reaction had the advantages of green solvent, good yield, and operational simplicity.

  在四乙基苄基氯化铵 (TEBAC) 的催化下，芳香醛、丙二腈和 2-(1-(3-氯苯基)亚丙基)丙二腈在水性介质中的三组分反应在 90 °C 下得到 2-氨基-6-(3-氯苯基) -5-甲基-4-芳基环己-1,5-二烯-1,3,3-三甲腈衍生物。X射线衍射进一步证实了4e的结构。该三组分反应具有溶剂绿色、收率好、操作简单等优点。