3,3-bis(4-methylphenyl)-1-propene-1,1-dicarbonitrile | 674334-53-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3,3-bis(4-methylphenyl)-1-propene-1,1-dicarbonitrile
• 英文别名: 3,3-bis(4-methylphenyl)prop-1-ene-1,1-dicarbonitrile；2-[2,2-Bis(4-methylphenyl)ethylidene]propanedinitrile
• CAS: 674334-53-3
• 化学式: C₁₉H₁₆N₂
• 分子量: 272.349
• InChiKey: QVUAGFJEZSKLGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 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：

  3,3-bis(4-methylphenyl)-1-propene-1,1-dicarbonitrile 在 硫酸 作用下， 反应 1.0h， 以60.3%的产率得到1-amino-6-methyl-4-(4-methylphenyl)naphthalene-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：

  1,2-双(4-甲基苯基)乙烷-1,2-二醇 在 哌啶 、 硫酸 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 0.08h， 生成 3,3-bis(4-methylphenyl)-1-propene-1,1-dicarbonitrile
  参考文献：
  名称：

  Novel synthesis of α-arylnaphthalenes from diphenylacetaldehydes and 1,1-diphenylacetones

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2006.03.054

文献信息

• Structural and energetic characterization of ylidenemalonodinitrile tautomers, precursors of fungicidal species
  作者：Jacek Grochowski、Pawel Serda、Michal Markiewicz、Bartlomiej Kozik、Janusz J. Sepiol

  DOI：10.1016/j.molstruc.2003.10.021

  日期：2004.2

  Ylidenemalonodinitrile (3,3-bis(4-chlorophenyl)-1-propene-1,1-dicarbonitrile), precursor of fungicidal compounds, synthesized in Knoevenagel reaction appears in solution in two forms, not separable by TLC chromatography. The ratio of both forms: that predicted from the Knoevenagel condensation scheme, and the second one, was preserved in the recrystallization cycle, as estimated from NMR spectra. It was assumed that forms corresponding to two tautomers originated by shifting a carbon-carbon double bond CAryl(2)HC-CH=C(CN)(2) vs. Aryl(2)C=CH-CH(CN)(2)). Crystal structure analysis identified in the solid state only one tautomer corresponding to the first form dominating in solution. In the refined model of the crystal structure both C=C bond and relevant hydrogen atoms were located univocally. Energy calculations carried out in vacuum and in solution confirmed energetic preference for tautomer present in the solid state. (C) 2003 Elsevier B.V. All rights reserved.