5,5,6,6-tetrafluoro-6-bromohexanal | 240140-56-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,5,6,6-tetrafluoro-6-bromohexanal
• 英文别名: 6-Bromo-5,5,6,6-tetrafluorohexanal
• CAS: 240140-56-1
• 化学式: C₆H₇BrF₄O
• 分子量: 251.019
• InChiKey: ZMYVMGCCIUMIAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,5,6,6-tetrafluoro-6-bromohexanal 在 正丁基锂 、 三(三甲基硅基)硅烷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.0h， 生成 6,6,7,7-tetrafluoroheptene
  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：

  6-bromo-5,5,6,6-tetrafluorohexan-1-ol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以42%的产率得到5,5,6,6-tetrafluoro-6-bromohexanal
  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