1,1,2,3,3-pentafluoro-1,5-hexadiene | 131768-26-8

• 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: 1,1,2,3,3-pentafluoro-1,5-hexadiene
• 英文别名: 1,5-Hexadiene, 1,1,2,3,3-pentafluoro-；1,1,2,3,3-pentafluorohexa-1,5-diene
• CAS: 131768-26-8
• 化学式: C₆H₅F₅
• 分子量: 172.098
• InChiKey: VQARNTIMQXQMLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,1,2,3,3-pentafluoro-1,5-hexadiene 在 溴 、 溶剂黄146 作用下， 以90%的产率得到5,6-dibromo-1,1,2,3,3-pentafluoro-1-hexene
  参考文献：
  名称：

  Synthesis of oxiranes based on 1,1,2,3,3-pentafluoro-1,5-hexadiene

  摘要：

  Interaction of 1,1,2,3,3-pentafluoro-1,5-hexadiene with Br-2: in a MeCOOH medium results in the product of selective bromination of the hydrocarbon double bond, 5,6-dibromo-1,1,2,3,3-pentafluoro-1-hexene. Epoxidation of the latter with H2O2 in an alkaline medium followed by debromination afforded 5,6-epoxy-4,4,5,6,6-pentafluoro-1-hexene for the first time.

  DOI：

  10.1007/bf00714432
• 作为产物：
  描述：

  4,4,5,6,6-pentafluoro-2-iodo-5-hexen-1-ol 在 锌 作用下， 以 乙二醇 为溶剂， 以79%的产率得到1,1,2,3,3-pentafluoro-1,5-hexadiene
  参考文献：
  名称：

  Gorbunova, T. I.; Kodess, M. I.; Podol'skii, A. V., Journal of general chemistry of the USSR, 1991, vol. 61, # 10, p. 2194 - 2195

  摘要：

  DOI：

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.
• Isomerization of 1,1,2,3,3-pentafluoro-1,5-hexadiene upon reaction with fluoride ions. First example of sequential anionotropic and prototropic allylic rearrangements
  作者：T. I. Gorbunova、M. I. Kodess、T. G. Khonina、T. I. Filyakova、A. V. Podol'skii、V. I. Saloutin

  DOI：10.1007/bf00869523

  日期：1992.2

  Upon heating in DMF medium with KF and 18-crown-6 1,1,2,2,3-pentafluoro-1,5-hexadiene (1) is converted to 4,5,6,6,6-pentafluoro-1,3-hexadiene and 1,1,1,2,3-pentafluoro-2,4-hexadiene. Reaction of (1) with KHF2 results in the formation of its HF addition product, namely, 4,4,5,6,6,6-hexafluoro-1-hexene. We assume that the driving force in the isomerization of (1) is the formation of conjugated products, involving both the fluorinated and nonfluorinated portions of the molecules, preferably with the minimum number of fluorine atoms attached to the double bond.
• The preparation and allylation of perfluoroallyl cadmium and copper reagents
  作者：Donald J. Burton、Yasuo Tarumi、Pamela L. Heinze

  DOI：10.1016/s0022-1139(00)80501-1

  日期：1990.11
• Reaction of 1,1,2,3,3-pentafluoro-1,5-hexadiene with methanol in the presence of a base
  作者：T. I. Gorbunova、A. Ya. Zapevalov、V. I. Saloutin

  DOI：10.1007/bf00699855

  日期：1994.4

  The reaction of 1,1,2,3,3-pentafluoro-1,5-hexadiene (I) with MeOH in the presence of MeONa results in products of substitution, rearrangement, hydro-, or dehydrofluorination, depending on the reaction conditions.
• PARTIALLY FLUORINATED POLYMERS AND PROCESS THEREFOR
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0783533B1

  公开（公告）日：1998-08-05