2-(4-Hydroxyphenyl)indene | 142363-96-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 2-(4-Hydroxyphenyl)indene
• 英文别名: 4-(1H-Inden-2-yl)phenol
• CAS: 142363-96-0
• 化学式: C₁₅H₁₂O
• 分子量: 208.26
• InChiKey: RABSNCGVQPGNDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-(4-甲氧基苯基)-1H-茚 在 氢溴酸 、 溶剂黄146 作用下， 反应 24.0h， 以15%的产率得到2-(4-Hydroxyphenyl)indene
  参考文献：
  名称：

  Regioselectivity and stereoselectivity in the photodimerization of rigid and semirigid stilbenes

  摘要：

  The (2-pi + 2-pi)-photodimerizations of 2-phenylindene (1), 2-(4-methoxyphenyl)indene (9), and 5,10-dihydroindeno[2,1-a]indene (2) were investigated in a variety of homogeneous and micellar solvents. Four isomeric photodimers were formed from 1 and 9: syn-head-to-tail, syn-head-to-head, anti-head-to-tail, and anti-head-to-head. Relative yields of these as well as syn/anti- and head-to-tail (ht)/head-to-head (hh) ratios were determined in various solvents and as a function of temperature. In 1 syn/anti ratios ranged from 1.07 to 1.62 and ht/hh ratios from 0.88 to 1.28. In 9 syn/anti ratios between 0.83 and 2.55 and ht/hh ratios between 0.4 and 1.2 were found; preferred formation of anti and hh products was observed in micellar solvents as expected from preorientation of reactants. Two photodimers (ht and hh) were found upon irradiation of 2. ht/hh ratios ranged from 0.89 to 1.56. The variations of these ratios can be understood on the basis of a kinetic scheme, in which individual excimer states as precursors of the respective dimers are involved.

  DOI：

  10.1021/jo00041a035

文献信息

• Regioselectivity and stereoselectivity in the photodimerization of rigid and semirigid stilbenes
  作者：Thomas Wolff、Friedrich Schmidt、Peter Volz

  DOI：10.1021/jo00041a035

  日期：1992.7

  The (2-pi + 2-pi)-photodimerizations of 2-phenylindene (1), 2-(4-methoxyphenyl)indene (9), and 5,10-dihydroindeno[2,1-a]indene (2) were investigated in a variety of homogeneous and micellar solvents. Four isomeric photodimers were formed from 1 and 9: syn-head-to-tail, syn-head-to-head, anti-head-to-tail, and anti-head-to-head. Relative yields of these as well as syn/anti- and head-to-tail (ht)/head-to-head (hh) ratios were determined in various solvents and as a function of temperature. In 1 syn/anti ratios ranged from 1.07 to 1.62 and ht/hh ratios from 0.88 to 1.28. In 9 syn/anti ratios between 0.83 and 2.55 and ht/hh ratios between 0.4 and 1.2 were found; preferred formation of anti and hh products was observed in micellar solvents as expected from preorientation of reactants. Two photodimers (ht and hh) were found upon irradiation of 2. ht/hh ratios ranged from 0.89 to 1.56. The variations of these ratios can be understood on the basis of a kinetic scheme, in which individual excimer states as precursors of the respective dimers are involved.