1,1,2,3,3-pentafluoro-5-iodo-6-phenoxy-1-hexene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,1,2,3,3-pentafluoro-5-iodo-6-phenoxy-1-hexene
• 英文别名: (4,4,5,6,6-pentafluoro-2-iodohex-5-enoxy)benzene
• 化学式: C₁₂H₁₀F₅IO
• 分子量: 392.107
• InChiKey: MRVNGPJOYGCJDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1,1,2,3,3-pentafluoro-5-iodo-6-phenoxy-1-hexene 在 锌 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以37%的产率得到1,1,2,3,3-pentafluoro-6-phenoxy-1-hexene
  参考文献：
  名称：

  A Facile Perfluoroallylation of Olefins

  摘要：

  The addition of F-allyl iodide to terminal alkenes is induced by a catalytic amount of copper powder in the absence of solvent at room temperature to 50 degrees C to give the corresponding 1:1 adducts in good yields. A variety of functional groups such as trimethylsilyl, alkyl, epoxy, ester, hydroxyl, bromo, ether, and phosphonate are tolerated in the addition reaction. This reaction also worked well with internal olefins such as cyclohexene, cyclopentene, and 4-octene. Reaction with dienes gives the corresponding linear adduct and cyclization adduct depending on the chain length of the dienes. With 1,7-octadiene, a bis(perfluoroallyl) product is formed, while a tetrahydrofuran derivative is obtained with diallyl ether. Reduction of the adducts with zinc in the presence of nickel dichloride in moist THF or zinc in moist DMF affords the perfluoroallyl derivatives. The adduct reacts with zinc in DMF to form a zinc reagent which couples with organic electrophiles in the presence of CuBr.

  DOI：

  10.1021/jo9719766
• 作为产物：
  描述：

  3-碘季戊四醇氟代丙烷-1 、 烯丙基苯基醚 在 铜 作用下， 以78%的产率得到1,1,2,3,3-pentafluoro-5-iodo-6-phenoxy-1-hexene
  参考文献：
  名称：

  A Facile Perfluoroallylation of Olefins

  摘要：

  The addition of F-allyl iodide to terminal alkenes is induced by a catalytic amount of copper powder in the absence of solvent at room temperature to 50 degrees C to give the corresponding 1:1 adducts in good yields. A variety of functional groups such as trimethylsilyl, alkyl, epoxy, ester, hydroxyl, bromo, ether, and phosphonate are tolerated in the addition reaction. This reaction also worked well with internal olefins such as cyclohexene, cyclopentene, and 4-octene. Reaction with dienes gives the corresponding linear adduct and cyclization adduct depending on the chain length of the dienes. With 1,7-octadiene, a bis(perfluoroallyl) product is formed, while a tetrahydrofuran derivative is obtained with diallyl ether. Reduction of the adducts with zinc in the presence of nickel dichloride in moist THF or zinc in moist DMF affords the perfluoroallyl derivatives. The adduct reacts with zinc in DMF to form a zinc reagent which couples with organic electrophiles in the presence of CuBr.

  DOI：

  10.1021/jo9719766

文献信息

• A Facile Perfluoroallylation of Olefins
  作者：Ba V. Nguyen、Zhen-Yu Yang、Donald J. Burton

  DOI：10.1021/jo9719766

  日期：1998.5.1

  The addition of F-allyl iodide to terminal alkenes is induced by a catalytic amount of copper powder in the absence of solvent at room temperature to 50 degrees C to give the corresponding 1:1 adducts in good yields. A variety of functional groups such as trimethylsilyl, alkyl, epoxy, ester, hydroxyl, bromo, ether, and phosphonate are tolerated in the addition reaction. This reaction also worked well with internal olefins such as cyclohexene, cyclopentene, and 4-octene. Reaction with dienes gives the corresponding linear adduct and cyclization adduct depending on the chain length of the dienes. With 1,7-octadiene, a bis(perfluoroallyl) product is formed, while a tetrahydrofuran derivative is obtained with diallyl ether. Reduction of the adducts with zinc in the presence of nickel dichloride in moist THF or zinc in moist DMF affords the perfluoroallyl derivatives. The adduct reacts with zinc in DMF to form a zinc reagent which couples with organic electrophiles in the presence of CuBr.