2-(4'-methoxyphenyl)-1-nitro-2-trinitromethylethane | 10125-65-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4'-methoxyphenyl)-1-nitro-2-trinitromethylethane
• 英文别名: 1-Methoxy-4-(1,1,1,3-tetranitropropan-2-yl)benzene
• CAS: 10125-65-2
• 化学式: C₁₀H₁₀N₄O₉
• 分子量: 330.211
• InChiKey: KBSIPKVCYOHYMY-UHFFFAOYSA-N

物化性质

• 沸点：
  437.6±45.0 °C(Predicted)
• 密度：
  1.538±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  193
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-(4'-methoxyphenyl)-1-nitro-2-trinitromethylethane 在 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以67 mg的产率得到4-甲氧基-β-硝基苯乙烯
  参考文献：
  名称：

  Photochemical Nitration by Tetranitromethane. Part XLII. Photolysis of Some 4-Methoxystyrene Derivatives with Tetranitromethane.

  摘要：

  The photochemical reaction of 4-methoxystyrene (2a) with tetranitromethane in dichloromethane gives the nitro-trinitromethyl adduct, 2-(4'-methoxyphenyl)-1-nitro-2-trinitromethylethane (1), which on chromatography on silica gel yields the (E)-nitroalkene, (E)-4'-methoxy-2-nitrostyrene (3); in acetonitrile solution adduct 1 is also the major product together with minor adducts. Similar reaction of trans-1-(4'-methoxyphenyl)-1-propene (2b) in dichloromethane gives exclusively the stereoisomeric nitro-trinitromethyl adducts, 1-(4'-methoxyphenyl)-2-nitro-1-trinitromethylpropanes 6 and 7, but in acetonitrile adduct 7 is the major product together with a small amount of adduct 6 and a mixture of minor adducts. The base-catalysed reactions of adducts 1 and 6 gave nitroalkenes (E)-4'-methoxy-2-nitrostyrene (3) and (E)-1-(4'-methoxyphenyl)-2-nitro-1-propene (8), respectively, but reaction of adduct 7 gave a product of unknown structure. Kinetic studies of the base-catalysed reactions of nitro-trinitromethyl adducts 1, 6 and 7, and a nitro-trinitromethyl adduct derived from naphthalene, cis-1-nitro-4-trinitromethyl-1,4-dihydronaphthalene, are reported. A mixture of (E)- and (Z)-4-methoxycinnamonitrile did not react on extended photolysis with tetranitromethane. The photochemical reactions of 4-methoxystyrenes 2a and 2b with tetranitromethane are assumed to proceed via a radical chain reaction mechanism.

  DOI：

  10.3891/acta.chem.scand.52-0745
• 作为产物：
  描述：

  三硝基甲烷 、 1-(4-甲氧苯基)-2-硝基乙烯 在 哌啶 作用下， 以 乙醇 为溶剂， 生成 2-(4'-methoxyphenyl)-1-nitro-2-trinitromethylethane
  参考文献：
  名称：

  单和多硝基烷烃的研究II：取代的β-硝基苯乙烯的迈克尔反应

  摘要：

  描述了将2-硝基丙烷，宝石-二硝基烷烃和硝基仿的迈克尔加成到许多核取代的β-硝基苯乙烯上。研究了不同取代基和不同取代位置对β-硝基苯乙烯反应性的影响。

  DOI：

  10.1016/s0040-4020(01)99041-6