1,3-bis<4-(trifluoromethyl)phenyl>cyclopentaphenanthren-2-one | 108868-45-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 1,3-bis<4-(trifluoromethyl)phenyl>cyclopentaphenanthren-2-one
• 英文别名: 1,3-bis[4-(trifluoromethyl)phenyl]cyclopenta[l]phenanthren-2-one
• CAS: 108868-45-7
• 化学式: C₃₁H₁₆F₆O
• 分子量: 518.458
• InChiKey: WHHZJKXYUGNSMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.01
• 重原子数：
  38.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-carboxybenzene diazonium chloride 、 1,3-bis<4-(trifluoromethyl)phenyl>cyclopentaphenanthren-2-one 在 methyloxirane 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 5.0h， 以17%的产率得到9,14-bis<4-(trifluoromethyl)phenyl>benzotriphenylene
  参考文献：
  名称：

  A study of substituent effects on hydrogen-to-arene nonbonded interactions

  摘要：

  The polycylic aromatic hydrocarbon 9,14-diphenylbenzo[b]triphenylene is strongly twisted due to nonbonded interactions between hydrogen atoms on the polycyclic nucleus and the pi systems of the phenyl groups. Ten derivatives of 9,14-diphenylbenzo[b]triphenylene, with a wide variety of substituents on the phenyl groups, were synthesized and crystallographically characterized in order to test for the presence of electronic substituent effects on the magnitude of these hydrogen-to-arene nonbonded repulsions. The observed end-to-end twists in these compounds were the following: 9,14-diphenylbenzo[b]triphenylene (3) 40.4 +/- 0.4-degrees; 9,14-bis(4-nitrophenyl)-bezo[b]triphenylene (4), adopted a nontwisted conformation; 9,14-bis(4-methoxyphenyl)benzo[b]triphenylene (5), 36.8 +/- 1.3-degrees;9,14-bis[4-(methylthio)phenyl]benzo[b]triphenylene (6), 40.5+/-0.6-degrees;9,14-bis(4-chlorophenyl)-benzo[b]triphenylene (7), 39.4 +/- 0.5-degrees; 9,14-bromophenyl)benzo[b]triphenylene (8), 39.4+/-0.8-degrees;9,14-bis[4-(trifluoromethyl)phenyl]benzo[b]triphenylene (9), 36.3+/-1.5-degrees and 33.0 +/- 1.5-degrees (two crystallographically independent molecules); 9,14-bis(4-cyanophenyl)benzo[b]triphenylene (10), 38.2+/-0.5-degrees; 9,14-bis(4-methyl-phenyl)benzo[b]triphenylene (11), 43.1 +/- 0.4-degrees; 9,14-bis(4-nitrophenyl)-11-methylbenzo[b]triphenylene (12), 40.4 +/- 0.9-degrees and 33.4+/-0.9-degrees (two crystallographically independent molecules). The effects of the substituents and of crystal packing forces on the solid-state conformations of these compounds are discussed.

  DOI：

  10.1021/jo00002a037
• 作为产物：
  描述：

  4-三氟甲基苯乙酸 在 氢氧化钾 、 三乙胺 作用下， 以 乙醇 、 乙酸酐 为溶剂， 反应 2.08h， 生成 1,3-bis<4-(trifluoromethyl)phenyl>cyclopentaphenanthren-2-one
  参考文献：
  名称：

  纵向扭曲多环芳烃的合成与结构

  摘要：

  9,18-二苯基、9,18-双(4-氯苯基)-、9,18-双(4-(三氟甲基)苯基)-和9,18-双(4-异丙基苯基)四苯(a)的合成,c,hj) 蒽以及 9,18-二苯基四苯 (de,jk,op,uv) 并五苯被描述。前三种化合物的 X 射线晶体学分析表明它们因平面性而高度扭曲，蒽部分的端到端扭曲范围从 60.8/sup 0/ 到 69.7/sup 0/。使用双（异丙基苯基）衍生物的变温 NMR 实验表明，扭转反转的障碍约为 16.7 kcal/mol。

  DOI：

  10.1021/ja00249a032

文献信息

• Synthesis and structure of longitudinally twisted polycyclic aromatic hydrocarbons
  作者：Robert A. Pascal、William D. McMillan、Donna Van Engen、Robert Gregory Eason

  DOI：10.1021/ja00249a032

  日期：1987.7

  The syntheses of 9,18-diphenyl, 9,18-bis(4-chlorophenyl)-, 9,18-bis(4-(trifluoromethyl)phenyl)-, and 9,18-bis(4-isopropylphenyl)tetrabenz(a,c,hj)anthracene as well as 9,18-diphenyltetrabenz(de,jk,op,uv)pentacene are described. X-ray crystallographic analyses of the first three compounds show them to be highly distorted from planarity, with the end-to-end twists of the anthracene moieties ranging from

  9,18-二苯基、9,18-双(4-氯苯基)-、9,18-双(4-(三氟甲基)苯基)-和9,18-双(4-异丙基苯基)四苯(a)的合成,c,hj) 蒽以及 9,18-二苯基四苯 (de,jk,op,uv) 并五苯被描述。前三种化合物的 X 射线晶体学分析表明它们因平面性而高度扭曲，蒽部分的端到端扭曲范围从 60.8/sup 0/ 到 69.7/sup 0/。使用双（异丙基苯基）衍生物的变温 NMR 实验表明，扭转反转的障碍约为 16.7 kcal/mol。
• A study of substituent effects on hydrogen-to-arene nonbonded interactions
  作者：Robert P. L'Esperance、Donna Van Engen、Rajeev Dayal、Robert A. Pascal

  DOI：10.1021/jo00002a037

  日期：1991.1

  The polycylic aromatic hydrocarbon 9,14-diphenylbenzo[b]triphenylene is strongly twisted due to nonbonded interactions between hydrogen atoms on the polycyclic nucleus and the pi systems of the phenyl groups. Ten derivatives of 9,14-diphenylbenzo[b]triphenylene, with a wide variety of substituents on the phenyl groups, were synthesized and crystallographically characterized in order to test for the presence of electronic substituent effects on the magnitude of these hydrogen-to-arene nonbonded repulsions. The observed end-to-end twists in these compounds were the following: 9,14-diphenylbenzo[b]triphenylene (3) 40.4 +/- 0.4-degrees; 9,14-bis(4-nitrophenyl)-bezo[b]triphenylene (4), adopted a nontwisted conformation; 9,14-bis(4-methoxyphenyl)benzo[b]triphenylene (5), 36.8 +/- 1.3-degrees;9,14-bis[4-(methylthio)phenyl]benzo[b]triphenylene (6), 40.5+/-0.6-degrees;9,14-bis(4-chlorophenyl)-benzo[b]triphenylene (7), 39.4 +/- 0.5-degrees; 9,14-bromophenyl)benzo[b]triphenylene (8), 39.4+/-0.8-degrees;9,14-bis[4-(trifluoromethyl)phenyl]benzo[b]triphenylene (9), 36.3+/-1.5-degrees and 33.0 +/- 1.5-degrees (two crystallographically independent molecules); 9,14-bis(4-cyanophenyl)benzo[b]triphenylene (10), 38.2+/-0.5-degrees; 9,14-bis(4-methyl-phenyl)benzo[b]triphenylene (11), 43.1 +/- 0.4-degrees; 9,14-bis(4-nitrophenyl)-11-methylbenzo[b]triphenylene (12), 40.4 +/- 0.9-degrees and 33.4+/-0.9-degrees (two crystallographically independent molecules). The effects of the substituents and of crystal packing forces on the solid-state conformations of these compounds are discussed.