2-methyl-3-(phenylselenyl)propanenitrile

• 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: 2-methyl-3-(phenylselenyl)propanenitrile
• 英文别名: 2-methyl-3-(phenylseleno)propionitrile；2-Methyl-3-phenylselanylpropanenitrile
• 化学式: C₁₀H₁₁NSe
• 分子量: 224.164
• InChiKey: CNZCCJNGGLNAGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.59
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methyl-3-(phenylselenyl)propanenitrile 在 sodium azide 、 zinc dibromide 作用下， 以 水 为溶剂， 反应 24.0h， 以74%的产率得到5-(1-phenylselanylpropan-2-yl)-2H-tetrazole
  参考文献：
  名称：

  Synthesis of novel selenium and tellurium-containing tetrazoles: a class of chalcogen compounds with antifungal activity

  摘要：

  We describe herein the synthesis and antifungal activity of new 5-arylchalcogenoalkyl-1H-tetrazoles 4. Arylchalcogenoalkyl-1H-tetrazoles 4 have been synthesized in high yields by reaction of arylchalcogenolate anions with chloronitriles 2, and subsequent [2+3] cycloaddition of resulting arylchalcogenoalkylnitriles 3 with sodium azide by zinc catalysis in aqueous solution. The obtained compound 4a was screened for antifungal activity and presented inhibitory property against seven fungal strains. This protocol is an efficient method to produce new selenium-nitrogen compounds with antifungal activity. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2012.04.040
• 作为产物：
  描述：

  二苯基二硒醚 、 甲基丙烯腈 在 ruthenium trichloride 、 锌 、 air 作用下， 以 水 、 乙腈 为溶剂， 反应 3.5h， 以75%的产率得到2-methyl-3-(phenylselenyl)propanenitrile
  参考文献：
  名称：

  Zn/RuCl3 促进二硒化物的裂解：硒化锌与水介质中共轭烯烃的有效迈克尔加成

  摘要：

  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。

  DOI：

  10.1055/s-2007-984495

文献信息

• A Convenient Synthesis of ?-Phenylselenocarbonyl Compounds by In-TMSCl Promoted Cleavage of Diphenyl Diselenide and Subsequent Michael Addition
  作者：Brindaban?C. Ranu、Arijit Das

  DOI：10.1002/adsc.200404355

  日期：2005.4

  β-phenylselenocarbonyl compounds by a one-pot reaction of diphenyl diselenide and α,β-unsaturated ketones, aldehydes, esters and nitriles in the presence of indium metal-trimethylsilyl chloride under sonication. Presumably, the In-TMSCl reagent system reacts with diphenyl diselenide to form an intermediate, PhSeSiMe3, which then undergoes Michael addition with the α,β-unsaturated carbonyl compounds to produce

  已经开发了一种简单方便的方法，在金属铟-三甲基甲硅烷基氯的存在下，通过二苯二硒化物与α，β-不饱和酮，醛，酯和腈的一锅反应，合成β-苯基硒代羰基化合物。据推测，In-TMSCl试剂系统与二苯二硒化物反应形成中间体PhSeSiMe 3，然后将其与α，β-不饱和羰基化合物进行迈克尔加成反应，生成产物。
• .alpha.,.beta.-Unsaturated Nitriles: An Efficient Conjugate Addition with Potassium Benzeneselenolate and Potassium Benzenesulfenylate
  作者：Fraser F. Fleming、Joshua J. Pak

  DOI：10.1021/jo00118a060

  日期：1995.6
• 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。
• Synthesis of novel selenium and tellurium-containing tetrazoles: a class of chalcogen compounds with antifungal activity
  作者：Francieli M. Libero、Maurício C.D. Xavier、Francine N. Victoria、Patrícia S. Nascente、Lucielli Savegnago、Gelson Perin、Diego Alves

  DOI：10.1016/j.tetlet.2012.04.040

  日期：2012.6

  We describe herein the synthesis and antifungal activity of new 5-arylchalcogenoalkyl-1H-tetrazoles 4. Arylchalcogenoalkyl-1H-tetrazoles 4 have been synthesized in high yields by reaction of arylchalcogenolate anions with chloronitriles 2, and subsequent [2+3] cycloaddition of resulting arylchalcogenoalkylnitriles 3 with sodium azide by zinc catalysis in aqueous solution. The obtained compound 4a was screened for antifungal activity and presented inhibitory property against seven fungal strains. This protocol is an efficient method to produce new selenium-nitrogen compounds with antifungal activity. (C) 2012 Published by Elsevier Ltd.