1-Bromo-4-(3,3-difluoro-2-iodo-cycloprop-1-enyl)-benzene | 491593-80-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-Bromo-4-(3,3-difluoro-2-iodo-cycloprop-1-enyl)-benzene
• 英文别名: 1-Bromo-4-(3,3-difluoro-2-iodocyclopropen-1-yl)benzene
• CAS: 491593-80-7
• 化学式: C₉H₄BrF₂I
• 分子量: 356.936
• InChiKey: SWIDHGLDTXCECL-UHFFFAOYSA-N

物化性质

• 沸点：
  276.4±40.0 °C(Predicted)
• 密度：
  2.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  1-Bromo-4-(3,3-difluoro-2-iodo-cycloprop-1-enyl)-benzene 在 盐酸 作用下， 反应 6.0h， 以60%的产率得到(Z)-3-(4-bromophenyl)-3-iodoprop-2-enoic acid
  参考文献：
  名称：

  3,3-Difluoro-1-iodocyclopropenes:  A Simple Synthesis and Their Reactions

  摘要：

  The [1 + 2] cycloaddition reaction of 1-iodoalkynes with difluorocarbene, generated from the decomposition of FSO2CF2COOSiMe3 in diglyme in the presence of 10 mol % NaF at 120 degreesC, gives 3, 3-difluoro-1-iodocyclopropenes in good yields. These new iodides can be trifluoromethylated and functionalized via the Heck reaction. The unusual hydrolytic reactions of the iodides under acidic conditions was also investigated.

  DOI：

  10.1021/jo020431v
• 作为产物：
  描述：

  (4-溴苯基)乙炔 在 碘 、 sodium methylate 、 sodium fluoride 作用下， 以 甲醇 、 二乙二醇二甲醚 为溶剂， 反应 1.0h， 生成 1-Bromo-4-(3,3-difluoro-2-iodo-cycloprop-1-enyl)-benzene
  参考文献：
  名称：

  3,3-Difluoro-1-iodocyclopropenes:  A Simple Synthesis and Their Reactions

  摘要：

  The [1 + 2] cycloaddition reaction of 1-iodoalkynes with difluorocarbene, generated from the decomposition of FSO2CF2COOSiMe3 in diglyme in the presence of 10 mol % NaF at 120 degreesC, gives 3, 3-difluoro-1-iodocyclopropenes in good yields. These new iodides can be trifluoromethylated and functionalized via the Heck reaction. The unusual hydrolytic reactions of the iodides under acidic conditions was also investigated.

  DOI：

  10.1021/jo020431v

文献信息

• Difluorocarbene chemistry: synthesis of gem-difluorocyclopropenylalkynes and 3,3,3′,3′-tetrafluorobicyclopropyl-1,1′-dienes
  作者：Zhan-Ling Cheng、Qing-Yun Chen

  DOI：10.1016/j.jfluchem.2004.10.003

  日期：2005.1

  by the Sonogashira reaction of 3,3-difluoro-1-iodocyclopropenes with terminal alkynes. Onto these new alkynes addition of difluorocarbene, generated from the decomposition of FSO2CF2COOTMS in diglme in the presence of 10 mol% anhydrous NaF at 120 °C, gives 3,3,3′,3′-tetrafluorobicyclopropyl-1,1′-dienes. Acid hydrolysis of gem-difluorocyclopropenylalkynes in refluxing CH3OH affords the corresponding

  通过3，3-二氟-1-碘代环丙烯与末端炔的Sonogashira反应，可以容易地以高收率获得一系列宝石-二氟环丙烯基炔。在这些新的炔烃中，由FSO 2 CF 2 COOTMS在10 mol％无水NaF在120°C的条件下在乙二胺中分解生成的二氟卡宾，得到3,3,3'，3'-四氟双环丙基-1,1 '-二烯。宝石-二氟环丙烯基炔烃在回流的CH 3 OH中的酸水解得到相应的甲氧基羰基炔烃。
• 3,3-Difluoro-1-iodocyclopropenes:  A Simple Synthesis and Their Reactions
  作者：Wei Xu、Qing-Yun Chen

  DOI：10.1021/jo020431v

  日期：2002.12.1

  The [1 + 2] cycloaddition reaction of 1-iodoalkynes with difluorocarbene, generated from the decomposition of FSO2CF2COOSiMe3 in diglyme in the presence of 10 mol % NaF at 120 degreesC, gives 3, 3-difluoro-1-iodocyclopropenes in good yields. These new iodides can be trifluoromethylated and functionalized via the Heck reaction. The unusual hydrolytic reactions of the iodides under acidic conditions was also investigated.