difluoromethyl phenyl selenoxide | 147912-92-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: difluoromethyl phenyl selenoxide
• 英文别名: Phenyl(difluoromethyl) selenoxide；difluoromethylseleninylbenzene
• CAS: 147912-92-3
• 化学式: C₇H₆F₂OSe
• 分子量: 223.081
• InChiKey: CILWWBIVTXQAGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.12
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  difluoromethyl phenyl selenoxide 以 二氯甲烷 为溶剂， 生成 difluoro(phenylseleno)methyl ethyl ether
  参考文献：
  名称：

  醚的二氟苯基硒甲基化

  摘要：

  二氟甲基苯基亚硒酸酯与乙酸酐的Pummerer反应在CH 2 Cl 2的回流温度下进行，生成了二氟苯基硒代甲基碳阳离子当量，该当量可被环醚捕获，得到ω-（二氟苯基硒代甲氧基）烷基乙酸酯3。

  DOI：

  10.1016/s0040-4039(00)91782-9
• 作为产物：
  描述：

  sodium phenylselenide 在 双氧水 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 difluoromethyl phenyl selenoxide
  参考文献：
  名称：

  醚的二氟苯基硒甲基化

  摘要：

  二氟甲基苯基亚硒酸酯与乙酸酐的Pummerer反应在CH 2 Cl 2的回流温度下进行，生成了二氟苯基硒代甲基碳阳离子当量，该当量可被环醚捕获，得到ω-（二氟苯基硒代甲氧基）烷基乙酸酯3。

  DOI：

  10.1016/s0040-4039(00)91782-9
• 作为试剂：
  描述：

  四氢噻吩 在 difluoromethyl phenyl selenoxide 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到四甲基亚砜
  参考文献：
  名称：

  Reaction of Difluoromethyl Phenyl Selenoxide with Acetic Anhydride. A Route to Difluoro(phenylseleno)methylation of Ethers

  摘要：

  Difluoromethyl phenyl selenoxide (2) has been prepared and allowed to react with acetic anhydride in the presence of cyclic ethers and sulfides. Difluorophenylselenomethylation occurred smoothly on reacting 2 with Ac2O in refluxing dichloromethane to give omega-[difluoro(phenylseleno)methoxy]alkyl acetates 4 in 34-87% yields. A sequential reaction of Pummerer type rearrangement, difluorocarbene formation, electrophilic addition of the carbene to oxygen of ethers leading to oxonium ylide, and trapping with phenylselenenyl acetate is proposed.

  DOI：

  10.1021/jo00107a016

文献信息

• Perfluoroalkyl Selenoxides, Selenones and Selenoximines: General Preparation and Properties
  作者：Arnaud de Zordo‐Banliat、Kevin Grollier、Nicolas Vanthuyne、Sébastien Floquet、Thierry Billard、Guillaume Dagousset、Bruce Pégot、Emmanuel Magnier

  DOI：10.1002/anie.202300951

  日期：2023.3.13

  perfluoroalkyl selenoxides, selenones and selenoximines was possible through a selective oxidation of perfluoroalkyl selenoethers. Synthesis of perfluoroalkyl selenoxides was also described via a two-step one-pot reaction from selenocyanates. The perfluoroalkyl selenoximine family was synthesized. The Hansch-Leo parameters of the compounds were determined and some aryl perfluoroalkyl selenoxides were separated

  通过选择性氧化全氟烷基硒醚，可以获得全氟烷基硒氧化物、硒酮和硒肟。全氟烷基硒氧化物的合成也通过硒氰酸酯的两步一锅反应进行了描述。合成了全氟烷基硒肟家族。确定了化合物的 Hansch-Leo 参数，并通过手性 HPLC 分离了一些芳基全氟烷基硒氧化物。
• Uneyama Kenji, Maeda Kazuhiro, Tokunaga Yukio, Itano Nobuaki, J. Org. Chem., 60 (1995) N 2, S 370-375
  作者：Uneyama Kenji, Maeda Kazuhiro, Tokunaga Yukio, Itano Nobuaki

  DOI：——

  日期：——
• Reaction of Difluoromethyl Phenyl Selenoxide with Acetic Anhydride. A Route to Difluoro(phenylseleno)methylation of Ethers
  作者：Kenji Uneyama、Kazuhiro Maeda、Yukio Tokunaga、Nobuaki Itano

  DOI：10.1021/jo00107a016

  日期：1995.1

  Difluoromethyl phenyl selenoxide (2) has been prepared and allowed to react with acetic anhydride in the presence of cyclic ethers and sulfides. Difluorophenylselenomethylation occurred smoothly on reacting 2 with Ac2O in refluxing dichloromethane to give omega-[difluoro(phenylseleno)methoxy]alkyl acetates 4 in 34-87% yields. A sequential reaction of Pummerer type rearrangement, difluorocarbene formation, electrophilic addition of the carbene to oxygen of ethers leading to oxonium ylide, and trapping with phenylselenenyl acetate is proposed.
• Difluorophenylselenomethylation of ethers
  作者：Kenji Uneyama、Yukio Tokunaga、Kazuhiro Maeda

  DOI：10.1016/s0040-4039(00)91782-9

  日期：1993.2

  Pummerer reaction of difluoromethyl phenyl selenoxide with acetic anhydride proceeds at refluxing temperature of CH2Cl2, generating difluorophenylselenomethyl carbocation equivalent which can be trapped with cyclic ethers to give ω-(difluorophenylselenomethoxy)alkyl acetates 3.

  二氟甲基苯基亚硒酸酯与乙酸酐的Pummerer反应在CH 2 Cl 2的回流温度下进行，生成了二氟苯基硒代甲基碳阳离子当量，该当量可被环醚捕获，得到ω-（二氟苯基硒代甲氧基）烷基乙酸酯3。