diethyl 1,1-difluoro-3-iodo-6-oxoheptylphosphonate | 133827-44-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: diethyl 1,1-difluoro-3-iodo-6-oxoheptylphosphonate
• 英文别名: 7-Diethoxyphosphoryl-7,7-difluoro-5-iodoheptan-2-one
• CAS: 133827-44-8
• 化学式: C₁₁H₂₀F₂IO₄P
• 分子量: 412.152
• InChiKey: DDWCFGJFKNWPBN-UHFFFAOYSA-N

物化性质

• 沸点：
  393.5±42.0 °C(Predicted)
• 密度：
  1.502±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-已烯-2-酮 、 diethyl iododifluoromethylphosphonate 在 四(三苯基膦)钯 作用下， 以81%的产率得到diethyl 1,1-difluoro-3-iodo-6-oxoheptylphosphonate
  参考文献：
  名称：

  A novel and practical preparation of .alpha.,.alpha.-difluoro functionalized phosphonates from iododifluoromethylphosphonate

  摘要：

  The addition reaction of iododifluoromethylphosphonate 1 with alkenes is catalyzed by tetrakis(triphenylphosphine)palladium or copper metal under mild conditions. A variety of functional groups, including alkyl, trimethylsilyl, hydroxy, epoxy, acetoxy, ketone, and ester, in the alkenes could be tolerated under the reaction conditions. Reaction of 2 equiv of 1 with dienes gives the corresponding bisphosphonates. Although the palladium complex fails to induce addition of 1 to cyclohexene, the addition reaction proceeds readily with copper at 85-degrees-C. With diallyl ether, a tetrahydrofuran derivative is obtained. Electron scavenger and radical inhibitors suppressed the addition reaction completely. A single electron transfer initiated radical mechanism is proposed. Treatment of the adducts with zinc in the presence of nickel chloride in moist THF at room temperature provides the corresponding alpha,alpha-difluoro-functionalized phosphonates in good yields.

  DOI：

  10.1021/jo00043a027

文献信息

• A novel, general method for the preparation of α,gad̄ifluoro functionalized phosphonates
  作者：Zhen-Yu Yang、Donald J. Burton

  DOI：10.1016/s0040-4039(00)74476-5

  日期：1991.2

  The addition reaction of diethyl iododifluoromethylphosphonate to alkenes catalyzed by palladium in the absence of solvent gives the corresponding adducts in good yields at room temperature. A variety of functional groups in the alkenes, including alkyl, trimethylsilyl, hydroxy, epoxy, ketone and ester, are tolerated under the reaction conditions. The reduction of the adducts with nickel chloride and zinc in moist THF provides the title compounds.