2-(2,2-diphenylethylidene)propanedinitrile | 72227-96-4

• 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-(2,2-diphenylethylidene)propanedinitrile
• 英文别名: 3,3-diphenyl-1-propene-1,1-dicarbonitrile；3,3-diphenylprop-1-ene-1,1-dicarbonitrile；1,1-Dicyano-3,3-diphenyl-1-propen；Malononitrile, (2,2-diphenylethylidene)-
• CAS: 72227-96-4
• 化学式: C₁₇H₁₂N₂
• mdl: MFCD01715991
• 分子量: 244.296
• InChiKey: AJWQSBAALRXGHX-UHFFFAOYSA-N

物化性质

• 熔点：
  110-111 °C
• 沸点：
  451.8±45.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.058
• 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-(2,2-diphenylethylidene)propanedinitrile 在 硫酸 作用下， 反应 1.0h， 以90.3%的产率得到1-amino-4-phenylnaphthalene-2-carbonitrile
  参考文献：
  名称：

  Synthesis of α-arylnaphthalenes from diphenylacetaldehydes and 1,1-diphenylacetones

  摘要：

  Condensation of diphenylacetalclehydes and 1,1-diphenylacetones with malonodinitrile and cyclization of obtained aryl-ylidenemalonodinitriles in concentrated sulfuric acid leads to 1-amino-4-arylnaphthalene-2-carbonitriles. The benzannulation reaction is accompanied by a quasi-aromatic rearrangement. Preliminary tests of some synthesized aminonitriles have revealed their considerable biological activity against phytopathogenic fungi. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.04.067
• 作为产物：
  描述：

  联苯乙醛 、 丙二腈 在 polymers of carbon tetrachloride and ethylene diamine nanoparticles encapsulated in silicalite-1 zeolite shell 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 2-(2,2-diphenylethylidene)propanedinitrile
  参考文献：
  名称：

  One methyl group makes a major difference: shape-selective catalysis by zeolite nanoreactors in liquid-phase condensation reactions

  摘要：

  在包裹基本活性位点的沸石晶体上，可以实现具有一个甲基精度的形状选择性Knoevenagel缩合反应。

  DOI：

  10.1039/c7ta04187j

文献信息

• Tandem catalysis with a bifunctional site-isolated Lewis acid–Brønsted base metal–organic framework, NH2-MIL-101(Al)
  作者：Renganathan Srirambalaji、Soonsang Hong、Ramalingam Natarajan、Minyoung Yoon、Raghunandan Hota、Yonghwi Kim、Young Ho Ko、Kimoon Kim

  DOI：10.1039/c2cc36678a

  日期：——

  A metal–organic framework (MOF), NH2-MIL-101(Al), which acts as a bifunctional, site-isolated Lewis acid–Brønsted base heterogeneous catalyst, catalyzes a tandem Meinwald rearrangement–Knoevenagel condensation reaction with remarkable substrate selectivity.

  一种金属有机骨架（MOF），即NH2-MIL-101(Al)，作为一种双功能、位点隔离的路易斯酸-布朗斯坦碱异构催化剂，在麦恩瓦德重排-克诺文纳格尔缩合反应中表现出卓越的底物选择性。
• Novel pyridine catalysed reactions of dimethyl acetylenedicarboxylate (DMAD) and arylmethylidenemalononitriles: a stereoselective synthesis of highly substituted buta-1,3-dienes
  作者：Vijay Nair、B. Rema Devi、N. Vidya、Rajeev S. Menon、N. Abhilash、Nigam P. Rath

  DOI：10.1016/j.tetlet.2004.02.132

  日期：2004.4

  A pyridine catalysed addition of dimethyl acetylenedicarboxylate to various arylmethylidenemalononitriles to afford highly substituted 1,3-butadienes with complete stereoselectivity is described.

  描述了吡啶催化的乙炔二羧酸二甲酯向各种芳基亚甲基丙二腈的加成，以提供具有完全立体选择性的高度取代的1，3-丁二烯。
• Unusual organic photochemistry effected by cyano and methoxy substitution. Exploratory and mechanistic organic photochemistry
  作者：Howard E. Zimmerman、Diego Armesto、Mercedes G. Amezua、Thomas P. Gannett、Richard P. Johnson

  DOI：10.1021/ja00515a035

  日期：1979.10
• Novel synthesis of α-arylnaphthalenes from diphenylacetaldehydes and 1,1-diphenylacetones
  作者：Bartłomiej Kozik、Jarosław Wilamowski、Maciej Góra、Janusz J. Sepioł

  DOI：10.1016/j.tetlet.2006.03.054

  日期：2006.5

  A two-step synthesis of 1-amino-4-arylnaphthalene-2-carbonitriles from diphenylacetaldehydes and 1,1-diphenylacetones involves condensation of the carbonyl compounds with malonodinitrile and cyclization of the aryl-ylidenemalonodinitriles obtained in concentrated sulfuric acid. The benzannulation reaction is accompanied with a quasi-aromatic rearrangement. Some of synthesized aminonitriles reveal considerable biological activity against phytopathogenic fungi. (c) 2006 Elsevier Ltd. All rights reserved.
• The Huisgen 1,4-dipolar cycloaddition involving isoquinoline, dimethyl butynedioate and activated styrenes: a facile synthesis of tetrahydrobenzoquinolizine derivatives
  作者：Vijay Nair、B. Rema Devi、Luxmi R. Varma

  DOI：10.1016/j.tetlet.2005.06.014

  日期：2005.8

  A three-component reaction involving isoquinoline, dimethyl butynedioate and electrophilic styrenes is described. The reaction proceeds through a Huisgen 1,4-dipolar cycloaddition pathway. (c) 2005 Elsevier Ltd. All rights reserved.