3,3,4,4-tetrafluoro-4-bromobutyl vinyl ether | 240140-45-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: 3,3,4,4-tetrafluoro-4-bromobutyl vinyl ether
• 英文别名: 1-Bromo-4-ethenoxy-1,1,2,2-tetrafluorobutane
• CAS: 240140-45-8
• 化学式: C₆H₇BrF₄O
• 分子量: 251.019
• InChiKey: CKMNAZGODBDOSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,3,4,4-tetrafluoro-4-bromobutyl vinyl ether 在 三正丁基氢锡 作用下， 以 various solvent(s) 为溶剂， 反应 8.0h， 生成 3,3,4,4-tetrafluorobutyl vinyl ether
  参考文献：
  名称：

  Cyclizations of 5-Hexenyl, 6-Heptenyl, 7-Octenyl, and 8-Nonenyl Radicals. The Kinetic and Regiochemical Impact of Fluorine and Oxygen Substituents

  摘要：

  Using competition kinetic methodology, rate constants for cyclizations of a series of hydrofluorocarbon (HFC) and ether 5-hexenyl, 6-heptenyl, and 7-octenyl radicals have been determined. Remarkably large rate constants (>10(7) s(-1)) have been observed for 6-exo-cyclizations of 1,1,2,2-tetrafluoro- and 1,1,2,2,3,3,4,4,-octafluoro-6-heptenyl radicals (>10(3) those of analogous hydrocarbon radicals), whereas HFC hexenyl and heptenyl ethers exhibit lower cyclization reactivity, as do HFC 7-octenyl radical systems, which cyclize in an endo manner. HFC 8-nonenyl radicals were not observed to cyclize. The results can be rationalized in terms of transition state polar influences, though other factors may also play significant roles.

  DOI：

  10.1021/jo990544n
• 作为产物：
  描述：

  乙烯基乙醚 、 4-溴-3,3,4,4-四氟-1-丁醇 在 mercury(II) diacetate 作用下， 反应 18.0h， 以40%的产率得到3,3,4,4-tetrafluoro-4-bromobutyl vinyl ether
  参考文献：
  名称：

  Cyclizations of 5-Hexenyl, 6-Heptenyl, 7-Octenyl, and 8-Nonenyl Radicals. The Kinetic and Regiochemical Impact of Fluorine and Oxygen Substituents

  摘要：

  Using competition kinetic methodology, rate constants for cyclizations of a series of hydrofluorocarbon (HFC) and ether 5-hexenyl, 6-heptenyl, and 7-octenyl radicals have been determined. Remarkably large rate constants (>10(7) s(-1)) have been observed for 6-exo-cyclizations of 1,1,2,2-tetrafluoro- and 1,1,2,2,3,3,4,4,-octafluoro-6-heptenyl radicals (>10(3) those of analogous hydrocarbon radicals), whereas HFC hexenyl and heptenyl ethers exhibit lower cyclization reactivity, as do HFC 7-octenyl radical systems, which cyclize in an endo manner. HFC 8-nonenyl radicals were not observed to cyclize. The results can be rationalized in terms of transition state polar influences, though other factors may also play significant roles.

  DOI：

  10.1021/jo990544n