Ethyl 2,2-Difluoro-4-iodo-12-hydroxydodecanoate | 134682-26-1

• 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: Ethyl 2,2-Difluoro-4-iodo-12-hydroxydodecanoate
• 英文别名: Ethyl 2,2-difluoro-12-hydroxy-4-iodododecanoate
• CAS: 134682-26-1
• 化学式: C₁₄H₂₅F₂IO₃
• 分子量: 406.252
• InChiKey: FTWLJESVDXVRDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  20
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 2,2-Difluoro-4-iodo-12-hydroxydodecanoate 在 水 、 nickel dichloride 、 锌 作用下， 以 四氢呋喃 为溶剂， 以71%的产率得到Ethyl 2,2-Difluoro-12-hydroxydodecanoate
  参考文献：
  名称：

  A new approach to .alpha.,.alpha.-difluoro-functionalized esters

  摘要：

  The addition reaction of iododifluoroacetates to alkenes is initiated by copper powder (10-20 mol %) at 50-60-degrees-C. Both terminal and internal alkenes give good yields of adducts. The reaction is also applicable to alkenes containing a variety of functional groups, such as epoxy, hydroxy, ketone, ester, and phosphonate moieties. This reaction can be carried out either neat or in solvents such as hexane, benzene, acetonitrile, DMF, DMSO, and HMPA and is suppressed by p-dinitrobenzene and di-tert-butyl nitroxide. A single electron transfer initiated radical mechanism is proposed. In the presence of nickel dichloride hexahydrate, reduction of the adducts with zinc in moist THF provides the corresponding alpha,alpha-difluoro esters in good yields.

  DOI：

  10.1021/jo00017a026
• 作为产物：
  描述：

  9-十烯-1-醇 、 二氟碘乙酸乙酯 在 偶氮二异丁腈 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 以69%的产率得到Ethyl 2,2-Difluoro-4-iodo-12-hydroxydodecanoate
  参考文献：
  名称：

  方便的AIBN引发的碘代二氟乙酸乙酯向烯烃的自由基加成反应

  摘要：

  描述了由AIBN引发的4-碘-2，2-二氟乙酸乙酯向各种烯烃底物中的加成。该加成通常导致相应的加成产物以良好的至优异的产率，并且在反应条件下可以容许各种官能团。

  DOI：

  10.1016/j.jfluchem.2008.03.002

文献信息

• A convenient AIBN-initiated radical addition of ethyl iododifluoroacetate to alkenes
  作者：Leo Leung、Bruno Linclau

  DOI：10.1016/j.jfluchem.2008.03.002

  日期：2008.10

  The AIBN-initiated addition of ethyl 4-iodo-2,2-difluoroacetate to a variety of alkene substrates is described. The addition generally led to the corresponding addition products in good to excellent yields and various functional groups could be tolerated under the reaction conditions.

  描述了由AIBN引发的4-碘-2，2-二氟乙酸乙酯向各种烯烃底物中的加成。该加成通常导致相应的加成产物以良好的至优异的产率，并且在反应条件下可以容许各种官能团。
• A new approach to .alpha.,.alpha.-difluoro-functionalized esters
  作者：Zhen Yu Yang、Donald J. Burton

  DOI：10.1021/jo00017a026

  日期：1991.8

  The addition reaction of iododifluoroacetates to alkenes is initiated by copper powder (10-20 mol %) at 50-60-degrees-C. Both terminal and internal alkenes give good yields of adducts. The reaction is also applicable to alkenes containing a variety of functional groups, such as epoxy, hydroxy, ketone, ester, and phosphonate moieties. This reaction can be carried out either neat or in solvents such as hexane, benzene, acetonitrile, DMF, DMSO, and HMPA and is suppressed by p-dinitrobenzene and di-tert-butyl nitroxide. A single electron transfer initiated radical mechanism is proposed. In the presence of nickel dichloride hexahydrate, reduction of the adducts with zinc in moist THF provides the corresponding alpha,alpha-difluoro esters in good yields.