diphenyl(p-chlorophenylethynyl)selenonium triflate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: diphenyl(p-chlorophenylethynyl)selenonium triflate
• 英文别名: 2-(4-Chlorophenyl)ethynyl-diphenylselanium;trifluoromethanesulfonate
• 化学式: CF₃O₃S*C₂₀H₁₄ClSe
• 分子量: 517.815
• InChiKey: QOJFDUJYTCCNKL-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  65.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diphenyl(p-chlorophenylethynyl)selenonium triflate 在 四丁基碘化铵 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以82%的产率得到二苯硒醚
  参考文献：
  名称：

  Reactions of alkynylselenonium salts with tetrabutylammonium halides: Apparent umpolung of alkynyl moiety

  摘要：

  The reactions of alkynylselenonium salts with n-Bu4NX (X = I, Br, CI) in CH2Cl2 gave 1-halo-1-alkynes or phenacyl halide derivatives and selenide, while the reaction with F-. afforded a terminal alkyne and a selenoxide. Seemingly, the selenonium salts acted as alkynyl cations in the former case and as alkynyl anions in the latter case. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02492-7
• 作为产物：
  描述：

  diphenyl(phenylethynyl)selenonium triflate 在 四丁基氟化铵 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 diphenyl(p-chlorophenylethynyl)selenonium triflate
  参考文献：
  名称：

  Reactions of alkynylselenonium salts with tetrabutylammonium halides: Apparent umpolung of alkynyl moiety

  摘要：

  The reactions of alkynylselenonium salts with n-Bu4NX (X = I, Br, CI) in CH2Cl2 gave 1-halo-1-alkynes or phenacyl halide derivatives and selenide, while the reaction with F-. afforded a terminal alkyne and a selenoxide. Seemingly, the selenonium salts acted as alkynyl cations in the former case and as alkynyl anions in the latter case. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02492-7

文献信息

• Michael-type addition of hydroxide to alkynylselenonium salt: practical use as a ketoselenonium ylide precursor
  作者：Shin-ichi Watanabe、Shinsuke Asaka、Tadashi Kataoka

  DOI：10.1016/j.tetlet.2004.08.036

  日期：2004.9

  A novel synthetic method of ketodiphenylselenonium ylide from alkynylselenonium salt is described. A reaction of alkynylselenonium salt, hydroxide ion, and aldehyde in the presence of silver triflate and triethylamine gave oxiranylketones just as a trans-isomer in moderate to good yields, whereas benzoyl aziridine derivatives were obtained from the reaction with sodium p-toluenesulfonamide instead

  描述了一种从炔基硒鎓盐合成酮二苯基硒鎓叶立德的新方法。在三氟甲磺酸银和三乙胺的存在下，炔基硒鎓盐，氢氧根离子和醛的反应以中等至良好的收率得到了环氧乙烷基酮，就像反式异构体一样，而苯甲酰基氮丙啶衍生物是从与对甲苯磺酰胺钠而不是苯甲酰胺的反应中获得的。氢氧根离子