Ethyl 2,2-Difluoro-4-iodononanoate | 127224-10-6

• 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-iodononanoate
• CAS: 127224-10-6
• 化学式: C₁₁H₁₉F₂IO₂
• 分子量: 348.172
• InChiKey: GDFIPDBEORETQI-UHFFFAOYSA-N

物化性质

• 沸点：
  305.3±37.0 °C(Predicted)
• 密度：
  1.428±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 2,2-Difluoro-4-iodononanoate 在 水 、 nickel dichloride 、 锌 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到ethyl 2,2-difluorononanoate
  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：

  1-庚烯 、 二氟碘乙酸乙酯 在 铜 作用下， 以 neat (no solvent) 为溶剂， 反应 6.0h， 以76%的产率得到Ethyl 2,2-Difluoro-4-iodononanoate
  参考文献：
  名称：

  铜催化的碘代二氟乙酸盐与烯烃的加成反应

  摘要：

  在50℃至60℃下，通过铜粉（10-20mol％）将碘代二氟乙酸酯加到烯烃中。该反应可以在纯溶剂中或在己烷或苯作为溶剂中进行。末端烯烃和内部烯烃均具有良好的收率（65-83％）。用氢化三丁基锡还原加合物得到α，α-二氟乙酸酯。

  DOI：

  10.1016/s0022-1139(00)82877-8

文献信息

• Nickel-catalyzed reaction of iododifluoroacetates with alkenes and zinc: a novel and practical route to .alpha.,.alpha.-difluoro-functionalized esters and .alpha.,.alpha.,.omega.,.omega.-tetrafluoro diesters
  作者：Zhen Yu Yang、Donald J. Burton

  DOI：10.1021/jo00045a027

  日期：1992.9

  lododifluoroacetates 1a-c react with alkenes and zinc in the presence of nickel dichloride hexahydrate in THF at room temperature or 60-degrees-C to give the corresponding alpha,alpha-difluoro esters in good yields. The reaction is also applicable to alkenes containing a variety of functional groups such as trimethylsilyl, hydroxy, ketone, and ester moieties. The reaction of 1 works well with dienes; the products formed depend on the length of chain of the dienes. 1,8-Nonadiene and 1,5-hexadiene afford the alpha,alpha,omega,omega-tetrafluoro diesters, while 1,6-heptadiene gave a mixture of ethyl 2,2-difluoro-8-nonenoate (19) and the cyclopentyl-substituted alpha,alpha-difluoro ester 20. When diallyl ether was used as a substrate, only the tetrahydrofuran derivative 21 was formed. The nickel-catalyzed reaction can be suppressed by p-dinitrobenzene and hydroquinone. A single electron transfer initiated radical mechanism is proposed.
• YANG, ZHEN-YU;BURTON, DONALD J., J. FLUOR. CHEM., 45,(1989) N, C. 435-439
  作者：YANG, ZHEN-YU、BURTON, DONALD J.

  DOI：——

  日期：——
• 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.
• Copper catalyzed addition reaction of iododifluoroacetates to olefins
  作者：Zhen-Yu Yang、Donald J. Burton

  DOI：10.1016/s0022-1139(00)82877-8

  日期：1989.12

  The addition of iododifluoroacetates to alkenes is catalyzed by copper powder (10-20 mol %) at 50° to 60°C. The reaction can be carried out neat or in hexane or benzene as solvent. Both terminal and internal alkenes gave good yields (65-83%). Reduction of the adduct with tributyltin hydride provides the α, α-difluoroacetate.

  在50℃至60℃下，通过铜粉（10-20mol％）将碘代二氟乙酸酯加到烯烃中。该反应可以在纯溶剂中或在己烷或苯作为溶剂中进行。末端烯烃和内部烯烃均具有良好的收率（65-83％）。用氢化三丁基锡还原加合物得到α，α-二氟乙酸酯。