1,1-Difluoro-4-methyl-2,3-pentadiene | 132170-74-2

• 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: 1,1-Difluoro-4-methyl-2,3-pentadiene
• CAS: 132170-74-2
• 化学式: C₆H₈F₂
• 分子量: 118.126
• InChiKey: PVDMXKVYZHOQOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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-溴-3-甲基-1-丁炔 、 alkaline earth salt of/the/ methylsulfuric acid 以 N,N-二甲基甲酰胺 为溶剂， 以64%的产率得到1,1-Difluoro-4-methyl-2,3-pentadiene
  参考文献：
  名称：

  二氟甲基丙二烯的区域选择性制备[1]

  摘要：

  二氟甲基镉试剂与伯，仲和叔炔丙基氯反应，然后区域选择性地甲苯磺酸化，从而以良好的收率得到二氟甲基丙二烯。

  DOI：

  10.1016/s0022-1139(00)80373-5

文献信息

• Regioselective Preparation of Difluoromethyl Allenes [1]
  作者：Donald J. Burton、Greg A. Hartgraves

  DOI：10.1016/s0022-1139(00)80373-5

  日期：1990.7

  The difluoromethylcadmium reagent reacts with primary, secondary, and tertiary propargyl chlorides and tosylates regioselectively to give difluoromethyl allenes in good yields.

  二氟甲基镉试剂与伯，仲和叔炔丙基氯反应，然后区域选择性地甲苯磺酸化，从而以良好的收率得到二氟甲基丙二烯。
• Fluorinated organometallics: Perfluoroalkyl and functionalized perfluoroalkyl organometallic reagents in organic synthesis
  作者：Donald J. Burton、Zhen-Yu Yang

  DOI：10.1016/s0040-4020(01)88139-4

  日期：——
• 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.