1,3-dibromo-4-butoxy-1,1-difluorobutane | 182154-53-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3-dibromo-4-butoxy-1,1-difluorobutane
• CAS: 182154-53-6
• 化学式: C₈H₁₄Br₂F₂O
• 分子量: 324.003
• InChiKey: OYLOWLUOVLVPOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-dibromo-4-butoxy-1,1-difluorobutane 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48%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
• 作为产物：
  描述：

  烯丙基丁基醚 、 二溴二氟甲烷 在 C.I.酸性橙108 、 copper(l) chloride 作用下， 以 叔丁醇 为溶剂， 反应 48.0h， 以14%的产率得到1,3-dibromo-4-butoxy-1,1-difluorobutane
  参考文献：
  名称：

  Reactions of 1,3-Dibromo-1,1-difluoro Compounds with 1,8-Diazabicyclo[5.4.0]undec-7-ene

  摘要：

  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.

  DOI：

  10.1021/jo960992k

文献信息

• Highly Selective <i>gem</i>-Difluoroallylation of Organoborons with Bromodifluoromethylated Alkenes Catalyzed by Palladium
  作者：Qiao-Qiao Min、Zengsheng Yin、Zhang Feng、Wen-Hao Guo、Xingang Zhang

  DOI：10.1021/ja4114825

  日期：2014.1.29

  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.
• 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.