2,7-dimethyltetraphenylene | 1084894-37-0

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 2,7-dimethyltetraphenylene
• 英文别名: (4aZ,8aZ,12aZ,16aZ)-2,7-dimethyltetraphenylene
• CAS: 1084894-37-0
• 化学式: C₂₆H₂₀
• 分子量: 332.445
• InChiKey: XIGXQJCZIXRTIQ-CURPJEMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  2,7-dimethyltetraphenylene 反应 12.0h， 生成 9,10-苯并菲
  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：

  6,11-dimethyl-1,16-bis(trifluoromethanesulfonyloxy)tetraphenylene 在 甲酸 、 1,3-双(二苯基膦)丙烷 、 palladium diacetate 、 三乙胺 、 1,4-双(二苯基膦)丁烷 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以72%的产率得到2,7-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

• An Approach to Tetraphenylenes via Pd-Catalyzed C–H Functionalization
  作者：Hang Jiang、Yu Zhang、Dushen Chen、Bo Zhou、Yanghui Zhang

  DOI：10.1021/acs.orglett.6b00641

  日期：2016.5.6

  asymmetric catalysis. A facile and efficient approach is reported for the syntheis of tetraphenylene and its derivatives from 2-iodobiphenyls via Pd-catalyzed C–H activation. A range of substituted tetraphenylenes can be synthesized using this method, and the reaction can be performed on gram scale with relatively high efficiency, demonstrating its practical utility. This novel approach provides easy access

  四亚苯基不仅在理论上和实验上令人关注，而且在材料科学，超分子化学和不对称催化等许多领域中都有潜在的应用。据报道，一种简便有效的方法是通过Pd催化的C–H活化从2-碘代联苯合成四联苯及其衍生物。使用该方法可以合成许多取代的四亚苯基，并且该反应可以以相对较高的效率以克为单位进行，这证明了其实用性。这种新颖的方法提供了容易获得的四亚苯基，并应促进对这种迷人分子的应用的研究。
• 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.