2,2'-bis(2-hydroxyadamantan-2-yl)biphenyl | 1158597-97-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2,2'-bis(2-hydroxyadamantan-2-yl)biphenyl
• 英文别名: 2-[2-[2-(2-Hydroxy-2-adamantyl)phenyl]phenyl]adamantan-2-ol
• CAS: 1158597-97-7
• 化学式: C₃₂H₃₈O₂
• 分子量: 454.653
• InChiKey: MFTYDTWAFCQEAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2'-bis(2-hydroxyadamantan-2-yl)biphenyl 在 磷酸 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以85%的产率得到5,7-di(adamant-2-yl)-5,7-dihydrodibenzo[c,e]oxepine
  参考文献：
  名称：

  2,2′-Dilithiobiphenyl by direct lithiation of biphenylene

  摘要：

  The reaction of biphenylene (1) with an excess of lithium powder (1:14 molar ratio) and a catalytic amount of DTBB (10 mol %) in THF at room temperature leads to the formation of the dilithiated species 1 by reductive opening of the four-membered ring. Further reaction of this intermediate with different electrophiles [Electrophile = H2O, D2O, Me3SiCl, t-BuCHO, Et2CO, n-Pr2CO, (CH2)(5)CO, Ph2CO and adamantanonel at 0 degrees C yields the corresponding products 2, after hydrolysis with water. Cyclisation of some representative examples of compounds 2 with H3PO4 gives the corresponding dibenzoxepines 3. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.216
• 作为产物：
  描述：

  金刚烷酮 、 biphenyl-2,2'-diyl-bis-lithium 在 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 2,2'-bis(2-hydroxyadamantan-2-yl)biphenyl
  参考文献：
  名称：

  2,2′-Dilithiobiphenyl by direct lithiation of biphenylene

  摘要：

  The reaction of biphenylene (1) with an excess of lithium powder (1:14 molar ratio) and a catalytic amount of DTBB (10 mol %) in THF at room temperature leads to the formation of the dilithiated species 1 by reductive opening of the four-membered ring. Further reaction of this intermediate with different electrophiles [Electrophile = H2O, D2O, Me3SiCl, t-BuCHO, Et2CO, n-Pr2CO, (CH2)(5)CO, Ph2CO and adamantanonel at 0 degrees C yields the corresponding products 2, after hydrolysis with water. Cyclisation of some representative examples of compounds 2 with H3PO4 gives the corresponding dibenzoxepines 3. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.216