1-(4-tert-butylphenyl)-5,7-diethylindan-1-ol | 1111704-59-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 1-(4-tert-butylphenyl)-5,7-diethylindan-1-ol
• 英文别名: 1-(4-Tert-butylphenyl)-5,7-diethyl-2,3-dihydroinden-1-ol；1-(4-tert-butylphenyl)-5,7-diethyl-2,3-dihydroinden-1-ol
• CAS: 1111704-59-6
• 化学式: C₂₃H₃₀O
• 分子量: 322.491
• InChiKey: CIQDRGLGYDSPSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4-tert-butylphenyl)-5,7-diethylindan-1-ol 以 氘代氯仿 为溶剂， 生成 3-(4-tert-butylphenyl)-4,6-diethylindene
  参考文献：
  名称：

  Photocyclization of 2,4,6-triethylbenzophenones in the solid state

  摘要：

  Photocyclization of 2,4,6-triethylbenzophenones (TEBPs) into (E)- or (Z)-benzocyclobutenols ((E)- or (Z)-CBs) is E-selective in solution. By contrast, upon solid-state photolysis, TEBP-3,4-diCl and especially TEBP-4-t-Bu gave (Z)-CB relative to (E)-CB with a Much higher proportion than that in solution. For TEBP-4-t-Bu, the most major product in the solid state is an indanol derivative (Inol) (E/Z/Inol=1:3.9:10.3 at 9% conversion). On the basis of the X-ray crystallographic analysis, Inol and (Z)-CB are both topochemical products. Notably, the relative proportion of (E)-CB increased with increased conversion, namely with increased disruption of the crystal lattice. The DFT calculation of highly hindered 2,6-diisopropylbenzophenone (DIBP) was also conducted. These results in conjunction with the previous results on 2,4,6-triisopropylbenzophenones (TIBPs) indicate that CB is formed either via trans-enol followed by its conrotatory ring-closure (paths a and d) or through direct cyclization of biradical (BR) (path b) as shown in Scheme 1. Normally the former route is faster. However, in the crystalline state or in the case of sterically hindered phenyl ketones, path b tends to be adopted. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.10.105
• 作为产物：
  描述：

  2,4,6-triethyl-4'-tert-butylbenzophenone 反应 0.2h， 以68%的产率得到1-(4-tert-butylphenyl)-5,7-diethylindan-1-ol
  参考文献：
  名称：

  Photocyclization of 2,4,6-triethylbenzophenones in the solid state

  摘要：

  Photocyclization of 2,4,6-triethylbenzophenones (TEBPs) into (E)- or (Z)-benzocyclobutenols ((E)- or (Z)-CBs) is E-selective in solution. By contrast, upon solid-state photolysis, TEBP-3,4-diCl and especially TEBP-4-t-Bu gave (Z)-CB relative to (E)-CB with a Much higher proportion than that in solution. For TEBP-4-t-Bu, the most major product in the solid state is an indanol derivative (Inol) (E/Z/Inol=1:3.9:10.3 at 9% conversion). On the basis of the X-ray crystallographic analysis, Inol and (Z)-CB are both topochemical products. Notably, the relative proportion of (E)-CB increased with increased conversion, namely with increased disruption of the crystal lattice. The DFT calculation of highly hindered 2,6-diisopropylbenzophenone (DIBP) was also conducted. These results in conjunction with the previous results on 2,4,6-triisopropylbenzophenones (TIBPs) indicate that CB is formed either via trans-enol followed by its conrotatory ring-closure (paths a and d) or through direct cyclization of biradical (BR) (path b) as shown in Scheme 1. Normally the former route is faster. However, in the crystalline state or in the case of sterically hindered phenyl ketones, path b tends to be adopted. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.10.105