3-(phenylseleno)propionitrile | 67580-58-9

• 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-(phenylseleno)propionitrile
• 英文别名: 3-Phenylselanylpropanenitrile
• CAS: 67580-58-9
• 化学式: C₉H₉NSe
• 分子量: 210.137
• InChiKey: FNYXXPYXILTROJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.35
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  3-(phenylseleno)propionitrile 在 三甲基乙酸 作用下， 反应 2.0h， 生成 methyl 3-ethenyl-3,7-dimethyl-2-(phenylselanylmethyl)oct-6-enoate
  参考文献：
  名称：

  3-（苯基硒代）原丙酸三甲酯的Claisen原酸酯重排：用于合成2取代的丙烯酸酯和α-亚甲基-γ-丁内酯的合成子

  摘要：

  3-（苯基硒代）原丙酸三甲酯可以用作合成子，通过克莱森原酸酯与烯丙醇的重排，然后氧化消除PhSeOH，来制备2-取代的丙烯酸酯或α-亚甲基-γ-丁内酯。

  DOI：

  10.1016/s0040-4039(01)95318-3
• 作为产物：
  描述：

  β-氯丙腈 、 二苯基二硒醚 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 8.0h， 以73%的产率得到3-(phenylseleno)propionitrile
  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

文献信息

• 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。
• 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。
• 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。
• Reductive Cleavage of the Se–Se Bond by the Sm–Me3SiCl–H2O System: Preparation of Unsymmetrical Phenyl Selenides
  作者：Lei Wang、Yongmin Zhang

  DOI：10.1039/a803305f

  日期：——

  The reduction of diphenyl diselenide by the Sm–Me3SiCl–H2O system led to a selenide anion. This ‘living’ species reacted with organic halides, epoxides, α,β-unsaturated esters and α,β-unsaturated nitriles to afford unsymmetrical phenylselenides in good yields under mild and neutral conditions.

  通过Sm-Me3SiCl-H2O体系还原二苯基二硒醚，得到了一个硒化物阴离子。这种“活性”物种与有机卤化物、环氧化物、α,β-不饱和酯和α,β-不饱和腈反应，在温和中性条件下以良好产率得到了不对称的苯基硒化物。
• An Effective Synthesis of β- Selenium and β- Tellurium Carbonyl Compounds Via Reaction of Diaryldiselenides Or Diarylditellurides with α,β- Unsaturated Carbonyl Compounds Induced by Low-Valent Titanium
  作者：Long-Hu Zhou、Yong-Min Zhang

  DOI：10.1080/00397919908085796

  日期：1999.2

  Abstract P-Selenium and β-tellurium carbonyl compounds have been prepared in good yield by reaction of diaryldiselenides or diarylditelluride with α,β-unsaturated carbonyl compounds induced by TiC14 / Sm /THF system under mild reaction conditions.

  摘要 在温和的反应条件下，二芳基二硒化物或二芳基二碲化物与α,β-不饱和羰基化合物在TiCl4/Sm/THF体系诱导下反应，制备了P-硒和β-碲羰基化合物，收率良好。