3-(phenylselanyl)cyclohexanone | 71687-67-7

• 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: 3-(phenylselanyl)cyclohexanone
• 英文别名: 3-Phenylselanylcyclohexan-1-one
• CAS: 71687-67-7
• 化学式: C₁₂H₁₄OSe
• 分子量: 253.203
• InChiKey: HOWKGJREDVOGGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  (3-Methylidenecyclohexyl)selanylbenzene 以50%的产率得到
  参考文献：
  名称：

  Clive Derrick L. J., Postema Maarten H. D., J. Chem. Soc. Chem. Commun, (1994) N 2, S 235-236

  摘要：

  DOI：

文献信息

• Ceric ammonium nitrate (CAN) as a green and highly efficient promoter for the 1,4-addition of thiols and benzeneselenol to α,β-unsaturated ketones
  作者：Cheng-Ming Chu、Shijay Gao、M.N.V. Sastry、Chun-Wei Kuo、Chaowei Lu、Ju-Tsung Liu、Ching-Fa Yao

  DOI：10.1016/j.tet.2006.12.018

  日期：2007.2

  efficient process for the 1,4-addition of thiols and benzeneselenols to various α,β-unsaturated ketones using a catalytic amount of CAN with excellent product yields is described. This inexpensive, nontoxic, and readily available catalytic ceric(IV) ammonium nitrate system efficiently catalyzes conjugate addition reactions between thiol derivatives and various α,β-unsaturated ketones under solvent-free conditions

  描述了一种温和而有效的方法，该方法使用催化量的CAN以优异的产品收率将硫醇和苯硒酚的1,4-加成成各种α，β-不饱和酮。这种廉价，无毒且容易获得的催化硝酸铈（IV）铵体系可在无溶剂条件下有效催化硫醇衍生物与各种α，β-不饱和酮之间的共轭加成反应。提出了一种可能的机制，即CAN在自由基链加成反应中作为促进剂以及在共轭加成过程中的催化作用。
• 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。
• Selenium, carbon monoxide and water as a new reduction system: Reductive cleavage of disulfides and diselenides to thiols and selenols
  作者：Akiya Ogawa、Yutaka Nishiyama、Nobuaki Kambe、Shinji Murai、Noboru Sonoda

  DOI：10.1016/s0040-4039(00)95490-x

  日期：1987.1

  Disulfides and diselenides were effectively reduced to the corresponding thiols and selenols with carbon monoxide and water using selenium.

  使用硒将一氧化碳和水将二硫化物和二硒化物有效还原为相应的硫醇和硒醇。
• Synthesis of 1,1-Bis(seleno)-2-alkenes
  作者：R. Dieden、L. Hevesi

  DOI：10.1055/s-1988-27654

  日期：——

  The success of the direct conversion of α,β-unsaturated carbonyl compounds into the corresponding diselenoacetals by means of selenol/zinc chloride or tris(seleno)borane greatly depends on the starting carbonyl derivative. Enals and cyclic enones are transformed most efficiently, whereas acyclic enones mainly produce 1,4-addition compounds.

  直接将α,β-不饱和羰基化合物转化为对应的双硒缩醛的成功程度，很大程度上取决于起始羰基衍生物的性质。烯醛和环烯酮转化效率最高，而非环状烯酮主要生成1,4-加成产物。
• Zn/RuCl₃-Promoted Cleavage of Diselenides: An Efficient Michael Addition of Zinc Selenolates to Conjugated Alkenes in Aqueous Media
  作者：Barahman Movassagh、Ameneh Tatar

  DOI：10.1055/s-2007-984495

  日期：2007.7

  simple and highly efficient one-pot route to β-selenocarbonyl compounds and nitriles has been developed by Zn/RuCl 3 -catalyzed cleavage of diselenides and subsequent Michael addition of zinc selenolates to conjugated alkenes in aqueous media.

  通过 Zn/RuCl 3 催化的二硒化物裂解和随后的硒酸锌与水介质中的共轭烯烃的迈克尔加成，开发了一种简单高效的一锅法制备 β-硒羰基化合物和腈。