3-氟-5-正己基-4-碘-2-苯基呋喃 | 1016231-06-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 中文名称: 3-氟-5-正己基-4-碘-2-苯基呋喃
• 英文名称: 3-fluoro-5-n-hexyl-4-iodo-2-phenylfuran
• 英文别名: 4-Fluoro-2-hexyl-3-iodo-5-phenylfuran
• CAS: 1016231-06-3
• 化学式: C₁₆H₁₈FIO
• 分子量: 372.221
• InChiKey: BNRAEQVOZOGHBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-氟-5-正己基-4-碘-2-苯基呋喃 、 4-甲酰基苯硼酸 在 四(三苯基膦)钯 sodium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 1.5h， 以72%的产率得到4-(4-fluoro-2-hexyl-5-phenylfuran-3-yl)benzaldehyde
  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
• 作为产物：
  描述：

  2,2-difluoro-1-phenyl-dec-3-yn-1-ol 在 sodium carbonate 、 silica gel 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.08h， 以66%的产率得到3-氟-5-正己基-4-碘-2-苯基呋喃
  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.