2,2-difluoro-1-(4-hydroxyphenyl)-4-triethylsilylbut-3-yn-1-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,2-difluoro-1-(4-hydroxyphenyl)-4-triethylsilylbut-3-yn-1-ol
• 英文别名: 4-(2,2-Difluoro-1-hydroxy-4-triethylsilylbut-3-ynyl)phenol
• 化学式: C₁₆H₂₂F₂O₂Si
• 分子量: 312.432
• InChiKey: AYLXEIZPEKKVDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对羟基苯甲醛 、 3-bromo-3,3-difluoro-1-triethylsilylpropyne 在 indium 、 europium(III) trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 20.0h， 以62%的产率得到2,2-difluoro-1-(4-hydroxyphenyl)-4-triethylsilylbut-3-yn-1-ol
  参考文献：
  名称：

  Lanthanide Triflate-Catalyzed Preparation of β,β-Difluorohomopropargyl Alcohols in Aqueous Media. Application to the Synthesis of 4,4-Difluoroisochromans

  摘要：

  An indium-mediated Barbier-type reaction of difluoropropargyl bromide with several aldehydes in aqueous media was enhanced by a catalytic amount of a lanthanide triflate (5 mol %). The reaction gave the corresponding beta,beta-difluorohomopropargyl alcohols with high regioselectivity. The [2 + 2 + 2] alkyne cyclotrimerization of beta,beta-difluorohomopropargyl alcohols with monosubstituted acetylenes produced 4,4-difluoroisochromans in good yields with moderate regioselectivity.

  DOI：

  10.1021/jo0614588

文献信息

• gem-Difluoropropargylation of aldehydes using cat. In/Zn in aqueous media
  作者：Satoru Arimitsu、Jesse M. Jacobsen、Gerald B. Hammond

  DOI：10.1016/j.tetlet.2006.12.134

  日期：2007.2

  Zn (0.9 equiv) in combination with catalytic amounts of In (0.1 equiv) and I-2 (0.1 equiv) was found to effect the reaction of several difluoropropargyl bromide derivatives with aldehydes to produce gem-difluorohomopropargyl alcohols in aqueous media under conditions suitable for large scale applications. (c) 2007 Published by Elsevier Ltd.