3,3-difluoro-4-phenyl-4-(2-propynyloxy)-1-butyne | 916332-95-1

• 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: 3,3-difluoro-4-phenyl-4-(2-propynyloxy)-1-butyne
• 英文别名: (2,2-Difluoro-1-prop-2-ynoxybut-3-ynyl)benzene；(2,2-difluoro-1-prop-2-ynoxybut-3-ynyl)benzene
• CAS: 916332-95-1
• 化学式: C₁₃H₁₀F₂O
• 分子量: 220.219
• InChiKey: AXBNKYHHHOAPNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,3-difluoro-4-phenyl-4-(2-propynyloxy)-1-butyne 、 1-乙炔基-2,3,4,5,6-五氟苯 在 Wilkinson's catalyst 作用下， 以 苯 为溶剂， 反应 4.0h， 以15%的产率得到4,4-difluoro-7-pentafluorophenyl-3-phenylisochroman
  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
• 作为产物：
  描述：

  2,2-difluoro-1-phenyl-4-triisopropylsilylbut-3-yn-1-ol 在 四丁基氟化铵 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 29.0h， 生成 3,3-difluoro-4-phenyl-4-(2-propynyloxy)-1-butyne
  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

• Lanthanide Triflate-Catalyzed Preparation of β,β-Difluorohomopropargyl Alcohols in Aqueous Media. Application to the Synthesis of 4,4-Difluoroisochromans
  作者：Satoru Arimitsu、Gerald B. Hammond

  DOI：10.1021/jo0614588

  日期：2006.10.1

  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.