2,2-bis(4-dimethylaminophenyl)-4-hydroxymethyl-1,3-dioxolane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2-bis(4-dimethylaminophenyl)-4-hydroxymethyl-1,3-dioxolane
• 英文别名: [2,2-Bis[4-(dimethylamino)phenyl]-1,3-dioxolan-4-yl]methanol
• 化学式: C₂₀H₂₆N₂O₃
• 分子量: 342.438
• InChiKey: LKFIAYNNQRWTLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  45.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  硫代米氏酮 、 甘油 在 silver trifluoroacetate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以83%的产率得到2,2-bis(4-dimethylaminophenyl)-4-hydroxymethyl-1,3-dioxolane
  参考文献：
  名称：

  Acetal Formation by Metal Ion-mediated Desulfurization-Condensation of Thioketones with Diols and Phenols

  摘要：

  The acetal formation of thioketones with several diols and phenols through metal ion-mediated desulfurization-condensation was investigated. The reactivities of 4,4'-bis(dimethylamino)thiobenzophenone, ''thio-Michler's ketone'' (TMK) and xanthene-9-thione (XT) toward alpha,omega-alkanediols [HO(CH2)nOH, n = 2 similar to 4] in the presence of silver trifluoroacetate and triethylamine were compared. The reaction of TMK with glycerol, trans- and cis-1,2-cyclohexanediols, alpha, alpha'-dihydroxy-o-xylene and biphenyl-2,2-diol in the presence of silver salt gave the corresponding acetals in good yields. On the other hand, copper(I) chloride, in place of silver(I) salt, was useful for catechol and pyrogallol to give their acetals, respectively. It was thus found that thioketones are new and versatile acetalizing reagents for diols and phenols.

  DOI：

  10.3987/com-95-7375

文献信息

• Acetal Formation by Metal Ion-mediated Desulfurization-Condensation of Thioketones with Diols and Phenols
  作者：Isao Shibuya、Eisaku Katoh、Yasuo Gama、Akihiro Oishi、Yoichi Taguchi、Tohru Tsuchiya

  DOI：10.3987/com-95-7375

  日期：——

  The acetal formation of thioketones with several diols and phenols through metal ion-mediated desulfurization-condensation was investigated. The reactivities of 4,4'-bis(dimethylamino)thiobenzophenone, ''thio-Michler's ketone'' (TMK) and xanthene-9-thione (XT) toward alpha,omega-alkanediols [HO(CH2)nOH, n = 2 similar to 4] in the presence of silver trifluoroacetate and triethylamine were compared. The reaction of TMK with glycerol, trans- and cis-1,2-cyclohexanediols, alpha, alpha'-dihydroxy-o-xylene and biphenyl-2,2-diol in the presence of silver salt gave the corresponding acetals in good yields. On the other hand, copper(I) chloride, in place of silver(I) salt, was useful for catechol and pyrogallol to give their acetals, respectively. It was thus found that thioketones are new and versatile acetalizing reagents for diols and phenols.