12,15-dichloro<3.0>orthometacyclophane | 205439-93-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 12,15-dichloro<3.0>orthometacyclophane
• 英文别名: 12,15-Dichloro[3.0]orthometacyclophane；13,15-dichlorotricyclo[9.3.1.02,7]pentadeca-1(14),2,4,6,11(15),12-hexaene
• CAS: 205439-93-6
• 化学式: C₁₅H₁₂Cl₂
• 分子量: 263.166
• InChiKey: DLINNCSIKRYFMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  四氰基乙烯 、 12,15-dichloro<3.0>orthometacyclophane 以 氘代氯仿 为溶剂， 以100%的产率得到13,16-dichlorotetracyclo[11.3.1.02,7.011,16]heptadeca-1(17),2,4,6,11-pentaene-14,14,15,15-tetracarbonitrile
  参考文献：
  名称：

  12,15-Dichloro[3.0]orthometacyclophane:  A Highly Strained Biphenylophane

  摘要：

  The title compound, 3, in which two methylene groups of the parent compound 4 have been replaced by an ortho-substituted benzene ring, has been synthesized. It exists exclusively in the endo-conformation, in contrast to 4 for which the exo-conformation is preferred. High-level density functional calculations are presented for both compounds. They show that the endo-conformation of 3 is favored over the exo-conformation by 3.3 kcal mol(-1). The incorporation of a benzene ring in the bridge leads to a substantial increase of the strain energy (Delta SE = SE (3) - SE (4) = 4.7 kcal mol(-1)), making 3 the, thus far, smallest and most reactive, yet isolable, [n]metacyclophane.

  DOI：

  10.1021/ja973876n
• 作为产物：
  描述：

  3,3,15,15-tetrachloro[11,5.01,5][8]orthocyclophane 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 1.5h， 以87%的产率得到12,15-dichloro<3.0>orthometacyclophane
  参考文献：
  名称：

  12,15-Dichloro[3.0]orthometacyclophane:  A Highly Strained Biphenylophane

  摘要：

  The title compound, 3, in which two methylene groups of the parent compound 4 have been replaced by an ortho-substituted benzene ring, has been synthesized. It exists exclusively in the endo-conformation, in contrast to 4 for which the exo-conformation is preferred. High-level density functional calculations are presented for both compounds. They show that the endo-conformation of 3 is favored over the exo-conformation by 3.3 kcal mol(-1). The incorporation of a benzene ring in the bridge leads to a substantial increase of the strain energy (Delta SE = SE (3) - SE (4) = 4.7 kcal mol(-1)), making 3 the, thus far, smallest and most reactive, yet isolable, [n]metacyclophane.

  DOI：

  10.1021/ja973876n