3-(propargyloxy)-1,1-difluoro-2-(methoxy)pent-1-ene | 1026389-75-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(propargyloxy)-1,1-difluoro-2-(methoxy)pent-1-ene
• 英文别名: 1,1-Difluoro-2-(2-methoxyethoxymethoxy)-3-prop-2-ynoxypent-1-ene
• CAS: 1026389-75-2
• 化学式: C₁₂H₁₈F₂O₄
• 分子量: 264.269
• InChiKey: ZZEBBBUHQWMTOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(propargyloxy)-1,1-difluoro-2-(methoxy)pent-1-ene 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 10.25h， 生成 4,4-difluoro-3-hydroxy-5-(methoxy)-1-(triisopropylsilyl)oct-5-en-1-yne
  参考文献：
  名称：

  [2,3]-Wittig Rearrangements of Difluoroallylic Ethers. A Facile Entry to Highly Functionalized Molecules Containing a CF₂ Group

  摘要：

  Readily prepared primary, secondary, and tertiary difluoroallylic alcohols, derived from commercially available and inexpensive 2,2,2-trifluoroethanol, have been transformed into a range of difluoroallylic methyl ethers containing appropriate carbanion-stabilizing substituents. The [2,3]-Wittig rearrangements of these difluoroallylic ethers have been achieved cleanly, using lithium diisopropylamide in tetrahydrofuran at -30 degrees C, in excellent (secondary ether substrates) to good (primary and tertiary ether substrates) yields. Consequently, the approach allows convenient and rapid access to products containing a mid-chain CF2 group and with a useful level of functionality.

  DOI：

  10.1021/jo951516h
• 作为产物：
  描述：

  1,1-Difluoro-2-(2-methoxyethoxymethoxy)pent-1-en-3-ol 、 3-溴丙炔 在 sodium hydroxide 、 四丁基硫酸氢铵 作用下， 以51%的产率得到3-(propargyloxy)-1,1-difluoro-2-(methoxy)pent-1-ene
  参考文献：
  名称：

  [2,3]-Wittig Rearrangements of Difluoroallylic Ethers. A Facile Entry to Highly Functionalized Molecules Containing a CF₂ Group

  摘要：

  Readily prepared primary, secondary, and tertiary difluoroallylic alcohols, derived from commercially available and inexpensive 2,2,2-trifluoroethanol, have been transformed into a range of difluoroallylic methyl ethers containing appropriate carbanion-stabilizing substituents. The [2,3]-Wittig rearrangements of these difluoroallylic ethers have been achieved cleanly, using lithium diisopropylamide in tetrahydrofuran at -30 degrees C, in excellent (secondary ether substrates) to good (primary and tertiary ether substrates) yields. Consequently, the approach allows convenient and rapid access to products containing a mid-chain CF2 group and with a useful level of functionality.

  DOI：

  10.1021/jo951516h