bis(4-cyanobenzyl) diselenide | 84019-98-7

• 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: bis(4-cyanobenzyl) diselenide
• 英文别名: 4,4'-(diselanediylbis(methylene))dibenzonitrile；4-[[(4-Cyanophenyl)methyldiselanyl]methyl]benzonitrile
• CAS: 84019-98-7
• 化学式: C₁₆H₁₂N₂Se₂
• 分子量: 390.205
• InChiKey: YRTWEMSKYFQHCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对氰基氯苄 在 selenium dimer 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以0.90 mmol的产率得到bis(4-cyanobenzyl) diselenide
  参考文献：
  名称：

  硒化物（Se22-、Se2-）和碲化物（Te22- 和 Te2-）阴离子的超声诱导电化学合成

  摘要：

  Synthese des dianions du titre et added de chlorures benzyliques。Obtention de seleniure, diseleniure, Tellurure et ditellurure benzyliques

  DOI：

  10.1021/ja00305a070

文献信息

• Alternative Protocol for the Synthesis of Symmetrical Dibenzyl Diselenides and Disulfides
  作者：Vommina Sureshbabu、Veladi Panduranga、Girish Prabhu、Nageswara Panguluri

  DOI：10.1055/s-0035-1561579

  日期：——

  Abstract A one-pot protocol for the preparation of symmetrical dibenzyl diselenides and disulfides from the corresponding benzyl alcohols employing NaBH2Se3 and NaBH2S3 as selenium-transfer and sulfur-transfer reagent, respectively, is described. Structurally diverse substituted benzyl alcohols afforded the corresponding diselenides and disulfides in good to excellent yields. The protocol is simple and

  摘要 描述了一种通过一锅法从相应的苄醇制备对称的二苄基二硒化物和二硫化物的方法，分别使用NaBH 2 Se 3和NaBH 2 S 3作为硒转移剂和硫转移剂。结构上不同的取代苄醇以良好或优异的收率提供了相应的二硒化物和二硫化物。该方案简单温和，并且在短的反应时间内获得了产物。 描述了一种通过一锅法从相应的苄醇制备对称的二苄基二硒化物和二硫化物的方法，分别使用NaBH 2 Se 3和NaBH 2 S 3作为硒转移剂和硫转移剂。结构上不同的取代苄醇以良好或优异的收率提供了相应的二硒化物和二硫化物。该方案简单温和，并且在短的反应时间内获得了产物。
• Multistep Synthesis of Organic Selenides under Visible Light Irradiation: A Continuous-Flow Approach
  作者：Adrián A. Heredia、Silvia M. Soria-Castro、Willber D. Castro-Godoy、Ignacio D. Lemir、Martín López-Vidal、Fabricio R. Bisogno、Juan E. Argüello、Gabriela Oksdath-Mansilla

  DOI：10.1021/acs.oprd.9b00548

  日期：2020.4.17

  The potential application of multistep continuous-flow systems has had a great impact on the syntheses of active pharmaceutical ingredients, natural products, and commodity chemicals. In this report, the highly efficient combination of a chemical reduction and a photochemical Csp2–H activation reaction for selenylation of biologically relevant electron-rich arenes was achieved by means of a continuous-flow

  多步连续流系统的潜在应用对活性药物成分，天然产物和日用化学品的合成产生了巨大影响。在此报告中，化学还原和光化学C sp 2的高效组合用于生物相关的富电子芳烃的硒化反应的-H活化反应是通过连续流动过程实现的。首先，通过Rongalite还原了烷基和芳基硒氰酸酯，得到了相应的二硒化物。第二，Se-Se键的光活化导致富电子芳烃的硒化，这两个步骤都从良好的产率到优异的产率。在所有情况下，与间歇反应条件相比，反应时间都缩短了，分离的收率提高了。此外，即使在还原和光氧化转化相结合的情况下，以多步连续流顺序连接两个反应也是可能的。
• Highly chemoselective synthesis of functionalized diselenides from alkyl halides using benzyltriethylammonium tetrathiomolybdate
  作者：Kandikere R. Prabhu、Srinivasan Chandrasekaran

  DOI：10.1039/a701512g

  日期：——

  A variety of functionalized selenocyanates generated in situ from the corresponding alkyl halides undergo a facile reductive coupling on treatment with benzyltriethylammonium tetrathiomolybdate 1 under very mild conditions to give the corresponding diselenides in very good yields.

  多种功能化的硒氰酸酯可以通过相应的烷基卤化物原位生成，并在非常温和的条件下与四硫钼酸铵（benzyltriethylammonium tetrathiomolybdate 1）反应，发生简便的还原偶联反应，从而以很好的产率生成相应的二硒化物。
• Selenocyanates and diselenides: A new class of potent antileishmanial agents
  作者：Daniel Plano、Ylenia Baquedano、David Moreno-Mateos、María Font、Antonio Jiménez-Ruiz、Juan Antonio Palop、Carmen Sanmartín

  DOI：10.1016/j.ejmech.2011.04.054

  日期：2011.8

  Thirty five selenocyanate and diselenide compounds were subjected to in vitro screening against Leishmania infantum promastigotes and the most active ones were also tested in an axenic amastigote model. In order to establish the selectivity indexes (SI) the cytotoxic effect of each compound was also assayed against Jurkat and THP-1 cell lines.Thirteen derivatives exhibit better IC50 values than miltefosine and edelfosine. Bis(4-aminophenyl) diselenide exhibits the best activity when assayed in infected macrophages and one of the lowest cytotoxic activities against the human cell lines tested, with SI values of 32 and 24 against Jurkat and THP-1 cells, respectively. This compound thus represents a new lead for further studies aimed at establishing its mechanism of action. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Tetraethylammonium tetraselenotungstate: a new and efficient selenium transfer reagent for the chemoselective synthesis of functionalised diselenides
  作者：Vadivelu Saravanan、Emmanuel Porhiel、Srinivasan Chandrasekaran

  DOI：10.1016/s0040-4039(03)00286-7

  日期：2003.3

  A variety of functionalised organodiselenides were prepared in excellent yields from the corresponding halides and activated alcohols on treatment with tetraethylammonium tetraselenotungstate 1 under very mild conditions. (C) 2003 Elsevier Science Ltd. All rights reserved.