4-phenylseleno-2-nonanone | 1292308-86-1

• 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: 4-phenylseleno-2-nonanone
• 英文别名: 4-(phenylseleno)nonan-2-one；4-Phenylselanylnonan-2-one
• CAS: 1292308-86-1
• 化学式: C₁₅H₂₂OSe
• 分子量: 297.299
• InChiKey: CJUYCICFOROCKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苯硒酚 在 盐酸 、 sodium tetrahydroborate 作用下， 以 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 29.0h， 生成 4-phenylseleno-2-nonanone
  参考文献：
  名称：

  O-(tert-butyl) Se-phenyl selenocarbonate: A convenient, bench-stable and metal-free precursor of benzeneselenol

  摘要：

  A study by our laboratory shows that air, light and moisture stable O-(tert-butyl) Se-phenyl selenocarbonate could be employed as a safer, practical and efficient alternative to generate "in situ" benzeneselenol or benzeneselenolate anion under different and transition metal-free conditions. This procedure seems to be of general application since the nucleophilic selenium species obtained can be trapped by electrophiles such as alkyl halides, epoxides and electron-deficient alkenes and alkynes under different reaction conditions. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2020.131311

文献信息

• Face to face activation of a phenylselenium borane with α,β-unsaturated carbonyl substrates: facile synthesis of C–Se bonds
  作者：Xavier Sanz、Christopher M. Vogels、Andreas Decken、Carles Bo、Stephen A. Westcott、Elena Fernández

  DOI：10.1039/c4cc02098g

  日期：——

  Activated olefins directly react with a phenylselenium borane, at room temperature, without any metal or organocatalytic assistance. Up to 10 examples of β-(phenylseleno) substituted ketones and aldehydes have been prepared and theoretical evidence for the mechanism opens up non-existing pathways to create C–heteroatom bonds as a general tool.

  活化烯烃直接在室温下与苯硒基硼烷发生反应，无需任何金属或有机催化剂的辅助。已制备多达10个β-(苯硒基)取代的酮和醛实例，并为该机理提供了理论证据，揭示了作为通用工具创建碳-杂原子键的新途径。
• “On-Water” Michael-Type Addition Reactions Promoted by PhSeZnCl
  作者：Benedetta Battistelli、Testaferri Lorenzo、Marcello Tiecco、Claudio Santi

  DOI：10.1002/ejoc.201100045

  日期：2011.4

  communication we report that our reagent PhSeZnCl can be conveniently used to effect Michael addition like reactions of unsaturated ketones and electron-deficient alkynes, leading to synthetically useful β-seleno derivatives and vinyl selenides, respectively. The reactions are effected at room temperature in THF as well as under "on water" conditions. When the addition occurs on a triple bond, good stereoselectivity

  在这篇通讯中，我们报告说我们的试剂 PhSeZnCl 可以方便地用于影响不饱和酮和缺电子炔烃的迈克尔加成反应，分别导致合成有用的 β-硒代衍生物和乙烯基硒化物。反应在室温下在 THF 中以及在“水上”条件下进行。当加成发生在三键上时，观察到良好的立体选择性，并且反应在水悬浮液中显示出速率加速。