2,2-difluoro-3-iodo-4-triisopropylsilyl-2,5-dihydrofuran | 1016231-04-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 2,2-difluoro-3-iodo-4-triisopropylsilyl-2,5-dihydrofuran
• 英文别名: (5,5-difluoro-4-iodo-2H-furan-3-yl)-tri(propan-2-yl)silane
• CAS: 1016231-04-1
• 化学式: C₁₃H₂₃F₂IOSi
• 分子量: 388.312
• InChiKey: BXSGHXLSHRFOEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.52
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,1-difluoro-3-(triisopropylsilyl)-1,2-butadiene-4-ol 在 碘 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以60%的产率得到2,2-difluoro-3-iodo-4-triisopropylsilyl-2,5-dihydrofuran
  参考文献：
  名称：

  Synthesis of 2,4,5-Trisubstituted 3-Fluorofurans via Sequential Iodocyclization and Cross-Coupling of gem-Difluorohomopropargyl Alcohols

  摘要：

  The iodocyclization of gem-difluorohomoallenyl and gem-difluorohomopropargyl alcohols with I-2 and ICI, respectively, produced the corresponding,fluorinated iodofuran analogues in good yields. The iodo substituent in fluorinated 4-iodofurans was utilized as a synthetic handle to prepare multisubstituted 3-fluorofurans using a Suzuki cross-coupling reaction. The yields of both iodocyclization of gem-difluorohomopropargyl alcohol and subsequent Suzuki coupling were dramatically enhanced by microwave irradiation.

  DOI：

  10.1021/jo800088y

文献信息

• Synthesis of 2,4,5-Trisubstituted 3-Fluorofurans via Sequential Iodocyclization and Cross-Coupling of <i>gem</i>-Difluorohomopropargyl Alcohols
  作者：Satoru Arimitsu、Jesse M. Jacobsen、Gerald B. Hammond

  DOI：10.1021/jo800088y

  日期：2008.4.1

  The iodocyclization of gem-difluorohomoallenyl and gem-difluorohomopropargyl alcohols with I-2 and ICI, respectively, produced the corresponding,fluorinated iodofuran analogues in good yields. The iodo substituent in fluorinated 4-iodofurans was utilized as a synthetic handle to prepare multisubstituted 3-fluorofurans using a Suzuki cross-coupling reaction. The yields of both iodocyclization of gem-difluorohomopropargyl alcohol and subsequent Suzuki coupling were dramatically enhanced by microwave irradiation.