1,3-dinitrobicyclo<1.1.1>pentane | 148749-95-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 1,3-dinitrobicyclo<1.1.1>pentane
• 英文别名: Dinitrobicyclo[1.1.1]pentane；1,3-dinitrobicyclo[1.1.1]pentane
• CAS: 148749-95-5
• 化学式: C₅H₆N₂O₄
• 分子量: 158.114
• InChiKey: STBMAGHJTCWFGO-UHFFFAOYSA-N

物化性质

• 沸点：
  293.8±30.0 °C(predicted)
• 密度：
  1.58±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  1,3-dinitrobicyclo<1.1.1>pentane 在 草酰氯 作用下， 反应 120.0h， 生成 2,2-Dichloro-1,3-dinitrobicyclo<1.1.1>pentane
  参考文献：
  名称：

  2-Substituted bicyclo[1.1.1]pentanes

  摘要：

  A simple procedure has been developed for the conversion of 2-phenylbicyclo[1.1.1]pentan-2-ol to 2-phenyl-bicyclo[1.1.1]pentane. Oxidation gives bicyclo[1.1.1]pentane-2-carboxylic acid which may be converted to the amine, the nitro derivative, and the phenyl ketone. The pK(a) values for the carboxylic acid and related acids were determined, and the pK(s)'s of the amine hydrochloride and related compounds also were studied. The pK(a)'s of the amines were approximately linearly related to the percent s character determined from the (H-C)-H-1 NMR coupling constants. The pK(a) of the nitro derivative was determined, and the kinetic acidity of the phenyl ketone also was measured. The relationship of the differences in energy to the changes in strain energy is discussed. In an effort to prepare a compound with substituents at both the 1- and 2-positions, the reaction of 1,3-dinitrobicyclo[1.1.1]pentane with oxalyl chloride was examined. The reaction had a surprising course, leading to 2,2-dichloro-1,3-dinitrobicyclo[1.1.1]pentane.

  DOI：

  10.1021/jo00058a015
• 作为产物：
  描述：

  [1.1.1]螺桨烷 在 二氧化氮 作用下， 以 乙醚 为溶剂， 反应 0.25h， 以25%的产率得到1,3-dinitrobicyclo<1.1.1>pentane
  参考文献：
  名称：

  [1.1.1]丙烷的反应

  摘要：

  [1.1.1] 推进烷 (1) 的自由基加成反应进行了一些详细的描述，并允许制备各种 1,3-二取代双环 [1.1.1.] 戊烷。1 与自由基的反应比双环 [1.1.0] 丁烷 (2) 更快，而双环 [2.1.0] 戊烷 (3) 相对惰性

  DOI：

  10.1021/ja00162a022

文献信息

• Reactions of [1.1.1]propellane
  作者：Kenneth B. Wiberg、Sherman T. Waddell

  DOI：10.1021/ja00162a022

  日期：1990.3

  The free radical addition reactions of [1.1.1] propellane (1) are described in some detail and allowed the preparation of a wide variety of 1,3-disubstituted bicyclo [1.1.1.] pentanes. The reaction of 1 with free radicals was more rapid than that of bicyclo [1.1.0] butane (2), whereas bicyclo [2.1.0] pentane (3) was relatively inert

  [1.1.1] 推进烷 (1) 的自由基加成反应进行了一些详细的描述，并允许制备各种 1,3-二取代双环 [1.1.1.] 戊烷。1 与自由基的反应比双环 [1.1.0] 丁烷 (2) 更快，而双环 [2.1.0] 戊烷 (3) 相对惰性
• 2-Substituted bicyclo[1.1.1]pentanes
  作者：Kenneth B. Wiberg、Brenda S. Ross、John J. Isbell、Neil McMurdie

  DOI：10.1021/jo00058a015

  日期：1993.3

  A simple procedure has been developed for the conversion of 2-phenylbicyclo[1.1.1]pentan-2-ol to 2-phenyl-bicyclo[1.1.1]pentane. Oxidation gives bicyclo[1.1.1]pentane-2-carboxylic acid which may be converted to the amine, the nitro derivative, and the phenyl ketone. The pK(a) values for the carboxylic acid and related acids were determined, and the pK(s)'s of the amine hydrochloride and related compounds also were studied. The pK(a)'s of the amines were approximately linearly related to the percent s character determined from the (H-C)-H-1 NMR coupling constants. The pK(a) of the nitro derivative was determined, and the kinetic acidity of the phenyl ketone also was measured. The relationship of the differences in energy to the changes in strain energy is discussed. In an effort to prepare a compound with substituents at both the 1- and 2-positions, the reaction of 1,3-dinitrobicyclo[1.1.1]pentane with oxalyl chloride was examined. The reaction had a surprising course, leading to 2,2-dichloro-1,3-dinitrobicyclo[1.1.1]pentane.