diethyl 1,1-difluoro-3-iodo-5-carbethoxyhexylphosphonate | 133827-45-9

• 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: diethyl 1,1-difluoro-3-iodo-5-carbethoxyhexylphosphonate
• 英文别名: Ethyl 6-diethoxyphosphoryl-6,6-difluoro-4-iodo-2-methylhexanoate
• CAS: 133827-45-9
• 化学式: C₁₃H₂₄F₂IO₅P
• 分子量: 456.206
• InChiKey: OLWQBUNNAMLROZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-甲基-4-戊烯酸乙酯 、 diethyl iododifluoromethylphosphonate 在 四(三苯基膦)钯 作用下， 反应 0.5h， 以65%的产率得到diethyl 1,1-difluoro-3-iodo-5-carbethoxyhexylphosphonate
  参考文献：
  名称：

  A novel, general method for the preparation of α,gad̄ifluoro functionalized phosphonates

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)74476-5

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.