(Z)-5,5-difluoro-2-pentene | 92901-65-0

• 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: (Z)-5,5-difluoro-2-pentene
• 英文别名: (Z)-5,5-difluoropent-2-ene
• CAS: 92901-65-0
• 化学式: C₅H₈F₂
• 分子量: 106.115
• InChiKey: OTSDCLPGMKPHSY-IHWYPQMZSA-N

物化性质

• 沸点：
  48.3±8.0 °C(Predicted)
• 密度：
  0.915±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-氯-1-丁烯 、 alkaline earth salt of/the/ methylsulfuric acid 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (Z)-5,5-difluoro-2-pentene 、 (E)-5,5-difluoro-2-pentene 、 4,4-difluoro-3-methyl-1-butene
  参考文献：
  名称：

  The preparation of HCF2CdX and HCF2ZnX via direct insertion into the carbon halogen bond of CF2HY (Y=Br, I)

  摘要：

  The difluoromethylcadmium and zinc reagents have been prepared in DMF via direct insertion of Cd-0 into the carbon halogen bond of CF2HY (Y = Br, I). These reagents are stable at 65-75 degrees C and exhibit prolonged stability and activity at room temperature. Metathesis of the difluoromethylcadmium reagents with Cu(I)X (X = Br, Cl) at -55 degrees C rapidly produces difluoromethylcopper. The copper reagent is significantly less stable than the cadmium or zinc reagent and rapidly decomposes at room temperature. The difluoromethylcadmium and copper reagents exhibit good reactivity with allylic halides, propargylic derivatives and 1-iodoalkynes to provide good yields of the corresponding difluoromethylalkenes, difluoromethylallenes and difluoromethyl-2-alkynes. Alkylation is successful only with reactive alkyl halides. Generally, the difluoromethylcopper reagent is more reactive than the difluoromethylcadmium reagent and generally exhibits higher regioselectivity in reactions that can occur by either alpha- or -gamma-attack. (C) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2007.05.015

文献信息

• The preparation of HCF2CdX and HCF2ZnX via direct insertion into the carbon halogen bond of CF2HY (Y=Br, I)
  作者：Donald J. Burton、Greg A. Hartgraves

  DOI：10.1016/j.jfluchem.2007.05.015

  日期：2007.10

  The difluoromethylcadmium and zinc reagents have been prepared in DMF via direct insertion of Cd-0 into the carbon halogen bond of CF2HY (Y = Br, I). These reagents are stable at 65-75 degrees C and exhibit prolonged stability and activity at room temperature. Metathesis of the difluoromethylcadmium reagents with Cu(I)X (X = Br, Cl) at -55 degrees C rapidly produces difluoromethylcopper. The copper reagent is significantly less stable than the cadmium or zinc reagent and rapidly decomposes at room temperature. The difluoromethylcadmium and copper reagents exhibit good reactivity with allylic halides, propargylic derivatives and 1-iodoalkynes to provide good yields of the corresponding difluoromethylalkenes, difluoromethylallenes and difluoromethyl-2-alkynes. Alkylation is successful only with reactive alkyl halides. Generally, the difluoromethylcopper reagent is more reactive than the difluoromethylcadmium reagent and generally exhibits higher regioselectivity in reactions that can occur by either alpha- or -gamma-attack. (C) 2007 Elsevier B.V. All rights reserved.