2-(dinitromethylene)benzimidazole | 137143-81-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(dinitromethylene)benzimidazole
• 英文别名: 2-(Dinitromethylidene)-1,3-dihydrobenzimidazole
• CAS: 137143-81-8
• 化学式: C₈H₆N₄O₄
• 分子量: 222.16
• InChiKey: VDWJNXRMAJECDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,1-diiodo-2,2-dinitroethylene 、 邻苯二胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以66%的产率得到2-(dinitromethylene)benzimidazole
  参考文献：
  名称：

  Synthesis and reactions of 1,1-diiododinitroethylene

  摘要：

  The nitration of tetraiodoethylene gave 1,1-diiododinitroethylene (1). X-ray crystallography showed that one of the two nitro groups is perpendicular to the ethylene plane. Simple amines (dimethylamine, propylamine, aniline) reacted with 1 to give 1,1-diamino-2,2-dinitroethylene derivatives; diamines (o-phenylenediamine, ethylenediamine, 1,3-diaminopropane, 1,4-diaminobutane) gave the corresponding cyclic products, and a tetramine [(tetrakis(aminomethyl)methane] gave the analogous spiro derivative. Ammonia gave only ammonium cyanodinitromethide, whereas phenol gave 1,1-dinitro-2,2,2-triphenoxyethane. The reaction of 1 with potassium nitrite gave the dipotassium salt of tetranitroethane. X-ray crystallography of the 1,1-diamino-2,2-dinitroethylenes showed twisted olefins, some with twist angles greater than any previously reported for twisted ethylenes, with concomitant bond-distance distortions.

  DOI：

  10.1021/jo00027a042