2,2-difluoro-4-iodo-1-phenyldecan-1-one | 150542-07-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-difluoro-4-iodo-1-phenyldecan-1-one
• CAS: 150542-07-7
• 化学式: C₁₆H₂₁F₂IO
• 分子量: 394.243
• InChiKey: PILCKSRNOHSNRY-UHFFFAOYSA-N

物化性质

• 沸点：
  391.3±42.0 °C(Predicted)
• 密度：
  1.392±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  一氯二氟苯乙酮 在 四(三苯基膦)钯 、 碘 、 锌 作用下， 以 乙腈 为溶剂， 反应 8.5h， 生成 2,2-difluoro-4-iodo-1-phenyldecan-1-one
  参考文献：
  名称：

  Synthesis of .alpha.,.alpha.-Difluoro-Functionalized Ketones

  摘要：

  In the presence of a catalytic amount of tetrakis(triphenylphosphine) palladium [Pd(PPh(3))(4)], iododifluoromethyl alkyl and phenyl ketones 1 react with alkenes to give the corresponding alpha,alpha-difluoro-gamma-iodo ketones in high yields at room temperature either neat or in hexane at 60 degrees C. A variety of functional groups, such as alkyl, trimethylsilyl, hydroxy, epoxy, ketone, and ester, are tolerated under the reaction conditions. The reaction can be completely suppressed by a radical inhibitor, di-tert-butyl nitroxide or hydroquinone. A ring closure reaction occurs when 1 reacts with diethyl diallylmalonate in the presence of a catalytic amount of Pd(PPh(3))(4). Under UV irradiation, the reaction of 1 with diallyl ether gives a tetrahydrofuran derivative. All these results are consistent with a radical chain mechanism initiated by single electron transfer from Pd(PPh(3))(4) to 1. In the presence of a catalytic amount of nickel dichloride hexahydrate, the iodine in the 1:1 addition adducts is readily reduced by zinc in moist THF under mild conditions to give the corresponding alpha,alpha-difluoro ketones in high yields. A one-pot addition-reduction reaction has been developed for the synthesis of alpha,alpha-difluoro ketones without the isolation of the 1:1 addition adducts, which provides a new, efficient, and practical method for the preparation of a variety of alpha,alpha-difluoro-functionalized ketones.

  DOI：

  10.1021/jo00122a044

文献信息

• 一种β-碘代二氟丙酮类衍生物及其制备方法
  申请人：上海应用技术大学

  公开号：CN110627628A

  公开（公告）日：2019-12-31

  本发明涉及一种β‑碘代二氟丙酮类衍生物及其制备方法，通过将碘二氟酮类化合物原料与烯烃原料溶于溶剂中，再加入催化剂、1,10‑菲罗啉及碱性助剂，在惰性气体保护下反应，所得反应液晶萃取浓缩后，即得到目的产物β‑碘代二氟丙酮衍生物。与现有技术相比，本发明的制备方法简单、易于操作、产率高、经济适用性强，具有较好的工业化生产前景。
• 一种α,α-二氟酮类衍生物的制备方法
  申请人：上海应用技术大学

  公开号：CN112299981B

  公开（公告）日：2023-03-31

  本发明涉及一种α,α‑二氟酮类衍生物的制备方法，该方法为：将α,α,α‑碘二氟酮类化合物原料、不饱和烃、催化剂、配体以及锌粉混合，加入溶剂中，在惰性气体保护下反应，所得反应液分离提纯，即得到目的产物。与现有技术相比，本发明的制备方法具有高效、高选择性、高收率等优点，具有较好的工业化生产前景：本发明制备的α,α‑二氟酮类衍生物，具有良好的生理活性，在医药及农药领域具有较好的应用潜力。
• Cobalt Catalyzed Addition of α, α-Difluoroiodomethyl Ketones to Alkenes/ Alkynes
  作者：Jun Pan、Hanyang Li、Jingjing Wu、Fanhong Wu

  DOI：10.1016/j.jorganchem.2021.121818

  日期：2021.7

  difluoroalkylation reaction of alkenes/alkynes with difluoroacyl iodides was reported, which provided an efficient and convenient access to diverse α, α-difluoroketone derivatives. The mild conditions allow for a broad substrate scope including alkenes and alkynes, as well as good functional group toleration. Mechanism investigation showed that a difluoroalkyl radical is formed in the reaction pathway.

  据报道，烯烃/炔烃与二氟酰基碘的钴催化的二氟烷基化反应，提供了一种有效且方便的途径来获得各种α，α-二氟酮衍生物。温和的条件允许广泛的底物范围，包括烯烃和炔烃，以及良好的官能团耐受性。机理研究表明，在反应路径中形成了二氟烷基。
• Radical Difunctionalization of Alkenes with Iododifluoromethyl Ketones Under Ni‐Catalysis
  作者：Tianyu Zhang、Jun Pan、Jin Duan、Jingjing Wu、Wei Zhang、Fanhong Wu

  DOI：10.1002/cctc.201901395

  日期：2019.12.5

  Ni‐catalyzed radical difunctionalization of alkenes with iododifluoromethyl ketones was realized for the synthesis of α,α‐difluoroketones. This reaction can also be used for the construction of analogs containing 5‐membered heterocycles through radical addition and sequenced cyclization reactions.

  实现了镍与碘二氟甲基酮对烯烃的自由基催化双官能团的合成，用于合成α，α-二氟酮。该反应还可用于通过自由基加成和测序环化反应构建包含5元杂环的类似物。
• A general route to α,α-difluoroketones
  作者：Zai-Ming Qiu、Donald J. Burton

  DOI：10.1016/s0040-4039(00)73671-9

  日期：1993.5

  The reaction of iododifluoromethyl ketones with alkenes catalyzed by Pd(PPh3)4 in the absence of solvent at room temperature gives high yields of the corresponding 1:1 addition products. Treatment of the adducts with Zn/NiCl2.6H2O/THF affords alpha,alpha-difluoroketones. A variety of functional groups in the olefins are tolerated under the reaction conditions, including alkyl, trimethylsilyl, hydroxy, epoxy, carbonyl and ester groups.