Perfluoro-1,6-heptadiene | 4263-29-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: Perfluoro-1,6-heptadiene
• 英文别名: Perfluoroheptadien-1,6；Dodecafluoro-1,6-heptadiene；1,1,2,3,3,4,4,5,5,6,7,7-dodecafluorohepta-1,6-diene
• CAS: 4263-29-0
• 化学式: C₇F₁₂
• 分子量: 312.058
• InChiKey: MTLFIQQMQMABTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  Perfluoro-1,6-heptadiene 300.0~740.0 ℃ 、133.32 Pa 条件下， 反应 36.0h， 生成 cis-Perfluorobicyclo<3.2.0>heptane
  参考文献：
  名称：

  Thermal and Photochemistry of Perfluoro-1,6-heptadiene and the Perfluoro-1,3,6-heptatrienes

  摘要：

  Pyrolysis transformed the title diene (1) into a 9:1 mixture of perfluorobicyclo[3.1.1]heptane (2) and cis-perfluorobicyclo[3.2.0]heptane (3) at 300 degrees C and at > 450 degrees C principally into perfluarocyclopentene (11). Mercury-sensitized vapor phase photolysis of 1 also yielded 2 and 3, but the latter now dominated and its trans isomer 13 was formed as well. In the presence of nitrogen as a bath gas, the product was further enriched in the [3.2.0] isomers. Radical bromination of 1, a model reaction for the triplet photocyclization, gave cis- and trans-perfluoro-1,2-bis(bromomethyl)cyclopentane (IB). Configurations were assigned to the cis and trans isomers of perfluoro-1,3,6-heptatriene (19 and 20), and they were equilibrated with iodine/visible light (K-t-->c = 1.6(7) in CDCl3, 14 degrees C). The cis triene underwent electrocyclization at 133 degrees C to perfluoro-3-allylcyclobutene (27); thermal ring opening of this cyclobutene yielded exclusively the cis isomer. At 250 degrees C both the cis triene and the allylcyclobutene were transformed quantitatively into perfluorobicyclo[3.1.1]hept-2-ene (28). Trans triene gave no detectable cyclobutene over a range of temperatures, but yielded the [3.1.1] compound at 250 degrees C. Ultraviolet irradiation of cis triene produced the allylcyclobutene, and mercury photosensitization of either compound (or the trans triene) proceeded a step farther to give tricycloheptane valence isomers (31 and 32). The internal [2 + 2] cycloadditions described here contribute to our knowledge of the ground rules for reactions of this type in unsaturated fluorocarbons.

  DOI：

  10.1021/jo00106a019
• 作为产物：
  描述：

  Perfluoroazelaic acid sodium salt 300.0 ℃ 、133.32 Pa 条件下， 反应 6.0h， 生成 Perfluoro-1,6-heptadiene
  参考文献：
  名称：

  Thermal and Photochemistry of Perfluoro-1,6-heptadiene and the Perfluoro-1,3,6-heptatrienes

  摘要：

  Pyrolysis transformed the title diene (1) into a 9:1 mixture of perfluorobicyclo[3.1.1]heptane (2) and cis-perfluorobicyclo[3.2.0]heptane (3) at 300 degrees C and at > 450 degrees C principally into perfluarocyclopentene (11). Mercury-sensitized vapor phase photolysis of 1 also yielded 2 and 3, but the latter now dominated and its trans isomer 13 was formed as well. In the presence of nitrogen as a bath gas, the product was further enriched in the [3.2.0] isomers. Radical bromination of 1, a model reaction for the triplet photocyclization, gave cis- and trans-perfluoro-1,2-bis(bromomethyl)cyclopentane (IB). Configurations were assigned to the cis and trans isomers of perfluoro-1,3,6-heptatriene (19 and 20), and they were equilibrated with iodine/visible light (K-t-->c = 1.6(7) in CDCl3, 14 degrees C). The cis triene underwent electrocyclization at 133 degrees C to perfluoro-3-allylcyclobutene (27); thermal ring opening of this cyclobutene yielded exclusively the cis isomer. At 250 degrees C both the cis triene and the allylcyclobutene were transformed quantitatively into perfluorobicyclo[3.1.1]hept-2-ene (28). Trans triene gave no detectable cyclobutene over a range of temperatures, but yielded the [3.1.1] compound at 250 degrees C. Ultraviolet irradiation of cis triene produced the allylcyclobutene, and mercury photosensitization of either compound (or the trans triene) proceeded a step farther to give tricycloheptane valence isomers (31 and 32). The internal [2 + 2] cycloadditions described here contribute to our knowledge of the ground rules for reactions of this type in unsaturated fluorocarbons.

  DOI：

  10.1021/jo00106a019

文献信息

• Liquid toners with hydrocarbon solvents
  申请人：MINNESOTA MINING AND MANUFACTURING COMPANY

  公开号：EP0706095A1

  公开（公告）日：1996-04-10

  Polymeric dyes that comprise (a) segments that render the dyes soluble or dispersible in hydrocarbon solvents and (b) segments that impart color. The polymeric dyes can be introduced into hydrocarbon solvents or formed in hydrocarbon solvents to form stable colored dispersions, which can be used as toners for electrophotography. In these toners, the polymeric dye contains macromeric moieties that render the polymeric dye dispersible in hydrocarbon solvents. The polymeric dye may contain either a charge-directing chelating moiety or a surface-release promoting moiety or both of these moieties.

  聚合染料由(a)使染料在烃类溶剂中可溶或可分散的片段和(b)赋予颜色的片段组成。聚合染料可以引入到烃类溶剂中或在烃类溶剂中形成稳定的有色分散液，可用作电子摄影的色调剂。在这些色调剂中，聚合染料包含使聚合染料在烃类溶剂中分散的大分子基团。聚合染料可以包含电荷引导螯合基团或表面释放促进基团或这两种基团。
• Liquid toners for use with perfluorinated solvents
  申请人：MINNESOTA MINING AND MANUFACTURING COMPANY

  公开号：EP0594472A2

  公开（公告）日：1994-04-27

  An electrostatic liquid toner imaging process uses a liquid toner comprises a perfluorinated solvent and polymer resin-bound pigment particles. The polymer resin is preferably a resin containing highly fluorinated or perfluorinated units within the polymer resin or a resin comprising of at least 10% perfluorinated units, the rest comprising nonfluorinated units.

  静电液体墨粉成像工艺使用的液体墨粉由全氟溶剂和聚合物树脂结合的颜料颗粒组成。聚合物树脂最好是含有高氟或全氟化单元的树脂，或者是含有至少 10%全氟化单元，其余为非氟化单元的树脂。
• Liquid toners utilizing highly fluorinated solvents
  申请人：MINNESOTA MINING AND MANUFACTURING COMPANY

  公开号：EP0683436B1

  公开（公告）日：2000-03-22
• Jing Naiyong, Lemal David M., J. Org. Chem, 60 (1995) N 1, S 89-96
  作者：Jing Naiyong, Lemal David M.

  DOI：——

  日期：——
• US5397669A
  申请人：——

  公开号：US5397669A

  公开（公告）日：1995-03-14