(E)-1-bromo-1,1-difluoronon-2-ene | 154389-19-2

• 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: (E)-1-bromo-1,1-difluoronon-2-ene
• CAS: 154389-19-2
• 化学式: C₉H₁₅BrF₂
• 分子量: 241.119
• InChiKey: QLEACNJKCOQZTQ-BQYQJAHWSA-N

物化性质

• 沸点：
  218.1±35.0 °C(predicted)
• 密度：
  1.237±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-bromo-1,1-difluoronon-2-ene 在 六甲基磷酰三胺 、 三氯化铝 、 甲基锂 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 (E)-5-Chloro-3-fluoro-3-undecen-2-one
  参考文献：
  名称：

  1,1-二氟烯烃的新途径

  摘要：

  描述了一种合成各种1，1-二氟烯烃的新方法。关键步骤是在铜盐和锂盐的存在下，用有机金属试剂处理1-溴-1,1-二氟-2-烯烃。

  DOI：

  10.1016/s0040-4039(97)01363-4
• 作为产物：
  描述：

  1,3-dibromo-1,1-difluorononane 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以50%的产率得到(E)-1-bromo-1,1-difluoronon-2-ene
  参考文献：
  名称：

  Highly Selective gem-Difluoroallylation of Organoborons with Bromodifluoromethylated Alkenes Catalyzed by Palladium

  摘要：

  A first example of Pd-catalyzed gem-difluoroallylation of organoborons using 3-bromo-3,3-difluoropropene (BDFP) in high efficiency with high alpha/gamma-substitution regioselectivity has been developed. The reaction can also be extended to substituted BDFPs and has advantages of low catalyst loading (0.8 to 0.01 mol %), broad substrate scope, and excellent functional group compatibility, thus providing a facile route for practical application in drug discovery and development.

  DOI：

  10.1021/ja4114825

文献信息

• Stereoselective introduction of a bromo- (or chloro-) difluoromethyl allylic group
  作者：Frédérique Tellier、Raymond Sauvêtre

  DOI：10.1016/0040-4039(95)00703-f

  日期：1995.6

  A highly regio- and stereo-selective method for the introduction of a bromo- (or chloro-) difluoromethylene group into various unsaturated systems is described. The key step is the treatment of 1,1-difluoro-1-alken-3-ols with thionyl bromide or chloride.

  描述了用于将溴（或氯）二氟亚甲基引入各种不饱和体系中的高度区域选择性和立体选择性的方法。关键步骤是用亚硫酰溴或氯化物处理1,1-二氟-1-烯丙基-3-醇。
• Stereoselective synthesis of 1-bromo- (or 1-chloro-) 1,1-difluoro-2- alkenes
  作者：Frédérique Tellier、Raymond Sauvêtre

  DOI：10.1016/0022-1139(95)03340-8

  日期：1996.1

  A highly regio- and stereo-selective method for the introduction of a bromo- (or chloro-) difluoromethylene group into various unsaturated systems is described. The key step is the treatment of 1,1-difluoro-1-alken-3-ols with thionyl bromide (or chloride).

  描述了用于将溴（或氯）二氟亚甲基引入各种不饱和体系中的高度区域选择性和立体选择性的方法。关键步骤是用亚硫酰溴（或氯化物）处理1,1-二氟-1-链烯-3-醇。
• A convenient synthesis of bromodifluoromethyl-substituted alkenes
  作者：Chang-Ming Hu、Jian Chen

  DOI：10.1016/0022-1139(93)03051-m

  日期：1994.10

  Various functionalized bromodifluoromethyl-substituted alkenes have been prepared by addition of dibromodifluoromethane to functionalized alkenes promoted by a CrCl3/Fe bimetal redox system, followed by dehydrobromination with KF/Al2O3.
• Synthesis of bromodifluoromethyl-substituted alkenes. Potassium fluoride supported on alumina as a dehydrobrominating agent
  作者：Chang-Ming Hu、Jian Chen

  DOI：10.1016/0022-1139(93)02954-d

  日期：1994.1

  Potassium fluoride supported on alumina is an efficient dehydrobrominating agent. 1,3-Dibromo-1,1-difluoroalkanes - adducts of dibromodifluoromethane and alkenes - give bromodifluoromethyl-substituted alkenes 2 on dehydrobromination with this agent in good to excellent yields. Alkenes 2 were a mixture of Z- and E-isomers, with the former predominating. Functional groups such as ester, carbonyl, ethylenic and chloromethyl are not affected under such reaction conditions.
• Reactions of 1,3-Dibromo-1,1-difluoro Compounds with 1,8-Diazabicyclo[5.4.0]undec-7-ene
  作者：Seth Elsheimer、Christopher J. Foti、Michael D. Bartberger

  DOI：10.1021/jo960992k

  日期：1996.1.1

  Difluorodienes result from the double dehydrobromination of 4-aryl-1,3-dibromo-1,1-difluorobutanes with DBU. Attempted syntheses of analogous 4-alkyl or C-alkoxy dienes yield monoelimination products under mild conditions and unexpected trifluoro compounds under more vigorous conditions. 4-Aryl-1,1-difluoro-1,3-butadienes react rapidly with 4-phenyl-1,2,4-triazoline-3,5-dione in Diels-Alder reactions, but these dienes are unreactive toward several other electron-deficient and electron-rich dienophiles.