6,6-difluoro-6-(diethoxyphosphinyl)-4-iodohexanoic acid | 142635-50-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6,6-difluoro-6-(diethoxyphosphinyl)-4-iodohexanoic acid
• 英文别名: 6-Diethoxyphosphoryl-6,6-difluoro-4-iodohexanoic acid
• CAS: 142635-50-5
• 化学式: C₁₀H₁₈F₂IO₅P
• 分子量: 414.125
• InChiKey: SNWVDOPANWIYJR-UHFFFAOYSA-N

物化性质

• 沸点：
  407.9±45.0 °C(Predicted)
• 密度：
  1.622±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-戊烯酸 、 diethyl iododifluoromethylphosphonate 在 四(三苯基膦)钯 作用下， 以 正己烷 为溶剂， 反应 0.33h， 以79%的产率得到6,6-difluoro-6-(diethoxyphosphinyl)-4-iodohexanoic acid
  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 and practical preparation of .alpha.,.alpha.-difluoro functionalized phosphonates from iododifluoromethylphosphonate
  作者：Zhen Yu Yang、Donald J. Burton

  DOI：10.1021/jo00043a027

  日期：1992.8

  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.