6-(2,3,4,5,6-Pentakis-phenylphenyl)-2,2-diphenylchromene | 1322004-69-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 6-(2,3,4,5,6-Pentakis-phenylphenyl)-2,2-diphenylchromene
• CAS: 1322004-69-2
• 化学式: C₅₇H₄₀O
• 分子量: 740.944
• InChiKey: CIFOYNVUMSLFQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.2
• 重原子数：
  58
• 可旋转键数：
  8
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.02
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-甲氧基-4-苯基乙炔苯 在 4-甲基苯磺酸吡啶 、 三溴化硼 作用下， 以 二苯醚 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 70.0h， 生成 6-(2,3,4,5,6-Pentakis-phenylphenyl)-2,2-diphenylchromene
  参考文献：
  名称：

  Influence of (2,3,4,5,6-Pentamethyl/phenyl)phenyl Scaffold: Stereoelectronic Control of the Persistence of o-Quinonoid Reactive Intermediates of Photochromic Chromenes

  摘要：

  Regioisomeric photochromic chromenes 1Ch-6Ch substituted with the (2,3,4,5,6-pentamethyl/phenyl)phenyl scaffold were designed to delve into stereoelectronic effects on the spectrokinetic properties of photogenerated o-quinonoid reactive intermediates. While the latter derived from 1Ch, 2Ch, 4Ch, and 5Ch were found to exhibit notable persistence, those from 3Ch and 6Ch were found to revert rapidly at room temperature to preclude visible coloration. The intermediates of 1Ch and 2Ch were found to be marginally more stable than those of 4Ch and 5Ch, respectively, attesting to the possibility of toroidal conjugation via C-ipso-pi orbitals in the former. The rapid reversion of the intermediates of 3Ch and 6Ch is attributed to unfavorable electronic repulsion between the phenyl ring of the (pentamethyl/phenyl)phenyl scaffold and one of the lone-pairs of the o-quinonoid oxygen. Thus, the regioisomerically substituted photochromic chromenes are shown to permit control of the reversion, very rapidly as well as slowly, of the colored o-quinonoid intermediates through operation of stereoelectronic effects differently.

  DOI：

  10.1021/jo201144t