2-Phenoxy-2-(trifluoromethyl)-4,4,5,5-tetraphenyl-1,3-dioxolane

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-Phenoxy-2-(trifluoromethyl)-4,4,5,5-tetraphenyl-1,3-dioxolane
• 英文别名: 2-Phenoxy-4,4,5,5-tetraphenyl-2-(trifluoromethyl)-1,3-dioxolane
• 化学式: C₃₄H₂₅F₃O₃
• 分子量: 538.566
• InChiKey: ZUNXTSCESHGZAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  40
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (1,2-二氯-1,2,2-三苯乙基)苯 、 silver trifluoroacetate 、 苯酚 以 二氯甲烷 为溶剂， 反应 2.5h， 以90%的产率得到2-Phenoxy-2-(trifluoromethyl)-4,4,5,5-tetraphenyl-1,3-dioxolane
  参考文献：
  名称：

  Synthesis of 2-Cyano-1,1,2,2-tetraphenylethyl Cation and Silver Ion Assisted Solvolysis of sym-Tetraphenylethylene Dichloride

  摘要：

  The reaction of 3-chloro-2,2,3,3-tetraphenylpropanenitrile (2) with AgSbF6 or SbCl5 below -55 degrees C in methylene chloride produces the stable, long-lived cation 2-cyano-1,1,2,2-tetraphenylethyl cation (5). Treatment of 5 with TMSCN affords a 98% yield of 2,2,3,3-tetraphenylsuccinonitrile. It was also found that cation 5 generated with AlCl3 at 0 degrees C can undergo intramolecular aromatic substitution to give 9-(cyanodiphenylmethyl)fluorene (8). In the reactions of sym-tetraphenylethylene dichloride (1) with CF3COOAg in the presence of methanol, it was found that tetraphenylethanone dimethyl ketal (9) can be synthesized in 91% yield. Because rearrangement occurred, 1-methoxy-1,2,2,2-tetraphenylethyl cation (15) is proposed as a reaction intermediate. In contrast, treatment of dichloride 1 with CF3CO2Ag in the presence of phenol or isopropyl or allyl alcohol did not produce the corresponding ketals but the 1,3-dioxolane ortho esters 19, 20, or 21 (2-alkoxy-2-(trifluoromethyl)-4,4,5,5-tetraphenyl-1,3-dioxolanes).

  DOI：

  10.1021/jo00123a032

文献信息

• Synthesis of 2-Cyano-1,1,2,2-tetraphenylethyl Cation and Silver Ion Assisted Solvolysis of sym-Tetraphenylethylene Dichloride
  作者：Shiming Wo、Herman E. Zieger、Michelle M. Millar、Stephen A. Koch

  DOI：10.1021/jo00123a032

  日期：1995.9

  The reaction of 3-chloro-2,2,3,3-tetraphenylpropanenitrile (2) with AgSbF6 or SbCl5 below -55 degrees C in methylene chloride produces the stable, long-lived cation 2-cyano-1,1,2,2-tetraphenylethyl cation (5). Treatment of 5 with TMSCN affords a 98% yield of 2,2,3,3-tetraphenylsuccinonitrile. It was also found that cation 5 generated with AlCl3 at 0 degrees C can undergo intramolecular aromatic substitution to give 9-(cyanodiphenylmethyl)fluorene (8). In the reactions of sym-tetraphenylethylene dichloride (1) with CF3COOAg in the presence of methanol, it was found that tetraphenylethanone dimethyl ketal (9) can be synthesized in 91% yield. Because rearrangement occurred, 1-methoxy-1,2,2,2-tetraphenylethyl cation (15) is proposed as a reaction intermediate. In contrast, treatment of dichloride 1 with CF3CO2Ag in the presence of phenol or isopropyl or allyl alcohol did not produce the corresponding ketals but the 1,3-dioxolane ortho esters 19, 20, or 21 (2-alkoxy-2-(trifluoromethyl)-4,4,5,5-tetraphenyl-1,3-dioxolanes).