1,16-dimethoxy-6,11-dimethyltetraphenylene | 1084894-38-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,16-dimethoxy-6,11-dimethyltetraphenylene
• 英文别名: (4aZ,8aZ,12aZ,16aZ)-1,16-dimethoxy-6,11-dimethyltetraphenylene
• CAS: 1084894-38-1
• 化学式: C₂₈H₂₄O₂
• 分子量: 392.497
• InChiKey: OPMXLANKGMLABM-UTUIIGMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,16-dimethoxy-6,11-dimethyltetraphenylene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到1,16-dihydroxy-6,11-dimethyltetraphenylene
  参考文献：
  名称：

  To Flip or Not To Flip? Assessing the Inversion Barrier of the Tetraphenylene Framework with Enantiopure 2,15-Dideuteriotetraphenylene and 2,7-Dimethyltetraphenylene

  摘要：

  Two chiral tetraphenylenes, 2,15-dideuteriotetraphenylene (7) and 2,7-dimethyltetraphenylene (15) were synthesized and resolved to address the tetraphenylene inversion barrier problem. Neutron diffraction investigation of enantiopure 7 showed that the molecule retained its chirality integrity during its synthesis from enantiopure precursors and therefore rules out the possibility of the tetraphenylene framework possessing a low-energy barrier to inversion. Thermal study on 15 and tetraphenylene I further revealed that their inversion barriers were not overcome up to 600 degrees C, at which temperature these compounds underwent skeletal contraction into triphenylene with activation energies of 62.8 and 58.2 kcal/mol, respectively. This result is supported by computational studies which yielded an inversion barrier of 135 kcal/mol for tetraphenylene as a consequence of the peri-hydrogen repulsions at its planar conformation.

  DOI：

  10.1021/jo802061p
• 作为产物：
  描述：

  2-碘-1-(2-碘-4-甲基苯基)-4-甲基苯 、 2,2'-dimethoxy-6,6'-diiodobiphenyl 在 正丁基锂 、 copper dichloride 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 0.5h， 以11%的产率得到1,16-dimethoxy-6,11-dimethyltetraphenylene
  参考文献：
  名称：

  To Flip or Not To Flip? Assessing the Inversion Barrier of the Tetraphenylene Framework with Enantiopure 2,15-Dideuteriotetraphenylene and 2,7-Dimethyltetraphenylene

  摘要：

  Two chiral tetraphenylenes, 2,15-dideuteriotetraphenylene (7) and 2,7-dimethyltetraphenylene (15) were synthesized and resolved to address the tetraphenylene inversion barrier problem. Neutron diffraction investigation of enantiopure 7 showed that the molecule retained its chirality integrity during its synthesis from enantiopure precursors and therefore rules out the possibility of the tetraphenylene framework possessing a low-energy barrier to inversion. Thermal study on 15 and tetraphenylene I further revealed that their inversion barriers were not overcome up to 600 degrees C, at which temperature these compounds underwent skeletal contraction into triphenylene with activation energies of 62.8 and 58.2 kcal/mol, respectively. This result is supported by computational studies which yielded an inversion barrier of 135 kcal/mol for tetraphenylene as a consequence of the peri-hydrogen repulsions at its planar conformation.

  DOI：

  10.1021/jo802061p

文献信息

• To Flip or Not To Flip? Assessing the Inversion Barrier of the Tetraphenylene Framework with Enantiopure 2,15-Dideuteriotetraphenylene and 2,7-Dimethyltetraphenylene
  作者：Hui Huang、Timothy Stewart、Matthias Gutmann、Takashi Ohhara、Nobuo Niimura、Yu-Xue Li、Jian-Feng Wen、Robert Bau、Henry N. C. Wong

  DOI：10.1021/jo802061p

  日期：2009.1.2

  Two chiral tetraphenylenes, 2,15-dideuteriotetraphenylene (7) and 2,7-dimethyltetraphenylene (15) were synthesized and resolved to address the tetraphenylene inversion barrier problem. Neutron diffraction investigation of enantiopure 7 showed that the molecule retained its chirality integrity during its synthesis from enantiopure precursors and therefore rules out the possibility of the tetraphenylene framework possessing a low-energy barrier to inversion. Thermal study on 15 and tetraphenylene I further revealed that their inversion barriers were not overcome up to 600 degrees C, at which temperature these compounds underwent skeletal contraction into triphenylene with activation energies of 62.8 and 58.2 kcal/mol, respectively. This result is supported by computational studies which yielded an inversion barrier of 135 kcal/mol for tetraphenylene as a consequence of the peri-hydrogen repulsions at its planar conformation.