1,1-二硝基-2-(对甲苯基)乙烯 | 109520-76-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,1-二硝基-2-(对甲苯基)乙烯
• 英文名称: 1,1-dinitro-2-(p-tolyl)ethene
• 英文别名: 1-(2,2-dinitroethenyl)-4-methylbenzene
• CAS: 109520-76-5
• 化学式: C₉H₈N₂O₄
• 分子量: 208.174
• InChiKey: BUJIDDXZDFSBOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1-二硝基-2-(对甲苯基)乙烯 在 sodium 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 51.0h， 生成 3-acetyl-2-methyl-5-nitro-4-(p-tolyl)-4,5-dihydrofuran
  参考文献：
  名称：

  Reaction of β,β-dinitrostyrenes with acetylacetone

  摘要：

  DOI：

  10.1007/s11178-005-0107-0
• 作为产物：
  描述：

  4-methyl-β-nitrostyrene 在 dinitrogen tetraoxide 作用下， 以 四氯化碳 为溶剂， 以65%的产率得到1,1-二硝基-2-(对甲苯基)乙烯
  参考文献：
  名称：

  β,β-Dinitrostyrenes: Specificity of synthesis and structure

  摘要：

  An improved procedure was developed for the synthesis of beta,beta-dinitrostyrenes, which increased the yield and reproducibility and made the products more accessible from the preparative viewpoint. Complex analysis of the spectral data (IR, UV, H-1 and C-13 NMR) and results of quantum-chemical calculations showed that 2-aryl-1,1-dinitroethene molecules have a structure in which one nitro group resides in the C=C bond plane while the other deviates from this plane. The C=C bond in 2-aryl-1,1-dinitroethene molecules was found to possess enhanced polarization and electrophilicity as compared to the corresponding bond in model mononitrostyrenes.

  DOI：

  10.1134/s1070363207110114

文献信息

• β,β-Dinitrostyrenes in reactions with cyclohexane-1,3-diones
  作者：E. V. Trukhin、E. A. Sheremet、V. M. Berestovitskaya

  DOI：10.1007/s11172-009-0278-x

  日期：2009.10

  The Michael-type addition of dimedone and dihydroresorcinol to β,β-dinitrostyrenes occurs easily without a catalyst. The adducts cyclize into 3-aryl-2-nitro-2,3,4,5,6-hexahydrobenzofuran-4-ones under the action of triethylamine.

  二甲酮和二氢间苯二酚与 β,β-二硝基苯乙烯的迈克尔型加成很容易在没有催化剂的情况下发生。在三乙胺的作用下，加合物环化成 3-芳基-2-硝基-2,3,4,5,6-六氢苯并呋喃-4-酮。
• Synthesis of 4-Aryl-5-nitro-1,2,3-triazoles
  作者：E. A. Sheremet、R. I. Tomanov、E. V. Trukhin、V. M. Berestovitskaya

  DOI：10.1023/b:rujo.0000036090.61432.18

  日期：2004.4
• Specific features of the reaction of β,β-dinitrostyrenes with indan-1,3-dione
  作者：E. A. Pabolkova、E. V. Trukhin、Ya. A. Kasem、V. M. Berestovitskaya

  DOI：10.1134/s1070363206080391

  日期：2006.8
• β,β-Dinitrostyrenes Reacted with Pyrrole
  作者：E. A. Sheremet、E. V. Trukhin、A. V. Skobeleva、V. M. Berestovitskaya

  DOI：10.1007/s10593-005-0202-8

  日期：2005.5
• β,β-Dinitrostyrenes: Specificity of synthesis and structure
  作者：V. M. Berestovitskaya、E. A. Pabolkova、A. V. Belyakov、E. V. Trukhin

  DOI：10.1134/s1070363207110114

  日期：2007.11

  An improved procedure was developed for the synthesis of beta,beta-dinitrostyrenes, which increased the yield and reproducibility and made the products more accessible from the preparative viewpoint. Complex analysis of the spectral data (IR, UV, H-1 and C-13 NMR) and results of quantum-chemical calculations showed that 2-aryl-1,1-dinitroethene molecules have a structure in which one nitro group resides in the C=C bond plane while the other deviates from this plane. The C=C bond in 2-aryl-1,1-dinitroethene molecules was found to possess enhanced polarization and electrophilicity as compared to the corresponding bond in model mononitrostyrenes.