(2-azido-2-phenylethyl)(phenyl)selane | 116316-12-2

• 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-azido-2-phenylethyl)(phenyl)selane
• 英文别名: (2-Azido-2-phenylethyl)selanylbenzene
• CAS: 116316-12-2
• 化学式: C₁₄H₁₃N₃Se
• 分子量: 302.237
• InChiKey: DNFRQMCTNAMSKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-azido-2-phenylethyl)(phenyl)selane 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 1-phenyl-2-(phenylseleno)ethanamine
  参考文献：
  名称：

  Novel azido-phenylselenenylation of double bonds. Evidence for a free-radical process

  摘要：

  A simple and mild azido-phenylselenenylation of terminal alkenes, which proceeds with complete anti-Markovnikov regioselectivity, has been developed. This reaction occurs when the alkenes are treated with (diacetoxyiodo)benzene, sodium azide, and diphenyl diselenide in dichloromethane at room temperature. The observed regioselectivity can be explained by assuming that the addition process is initiated by azido radicals. This was further supported by the results obtained starting from 1,6-heptadiene and from beta-pinene. Under the same conditions, efficient azido-phenylselenenylation of symmetrical olefins, 3,4-dihydro-2H-pyran, methyl acrylate, and vinyl crotonate can also be effected.

  DOI：

  10.1021/jo00024a020
• 作为产物：
  描述：

  苯基溴化硒 在 sodium azide 作用下， 以 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 11.0h， 生成 (2-azido-2-phenylethyl)(phenyl)selane
  参考文献：
  名称：

  N-Phenylselenosaccharin (NPSSac): a new electrophilic selenium-containing reagent

  摘要：

  A new reagent N-phenylselenosaccharin (NPSSac) was simply prepared and used as a source of the electrophilic phenylselenyl group. This relatively stable new compound was able to react with a series of electron rich organic molecules like alkenes in the presence of external or internal nucleophiles, activated aromatic substrates, or enolizable carbonyl derivatives, under very mild experimental conditions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.08.068

文献信息

• Phenylselenium azide addition to alkenes. A new and stereospecific introduction of Se and N into organic molecules.
  作者：Alfred Hassner、Ananda S. Amarasekara

  DOI：10.1016/s0040-4039(00)95624-7

  日期：——

  The first examples of direct introduction of PhSe and N3 functions by addition to olefins are reported. The addition of PhSeN3 to simple alkenes, as well as to activated alkenes takes place in the absence of a catalyst. The reaction proceeds stereospecifically but not regiospecifically, apparently via a 3-membered selenonium ion intermediate.

  报道了通过添加烯烃直接引入PhSe和N 3官能团的第一个实例。在没有催化剂的情况下，将PhSeN 3加到简单的烯烃以及活化的烯烃中。该反应显然是立体定向的，而不是区域特异性的，显然是通过一个三元硒离子中间体进行的。
• KI catalyzed azidoselenenylation of alkenes with sodium azide and diselenides via an oxidative cleavage of Se–Se bond
  作者：Yikun Zhang、Sixue Wu、Hongwei Shi、Jie Yan

  DOI：10.1080/10426507.2016.1192625

  日期：2016.10.2

  GRAPHICAL ABSTRACT ABSTRACT Using potassium iodide as a catalyst and m-chloroperbenzoic acid as an oxidant, an efficient catalytic procedure has been developed for the azidoselenenylation of alkenes with sodium azide and diselenides, and a series of corresponding β-azidoselenides, most of which are new compounds, have been prepared in moderate to good yields under mild reaction conditions. This in

  图形摘要摘要以碘化钾为催化剂，间氯过苯甲酸为氧化剂，开发了一种高效的催化方法，用于烯烃与叠氮化钠和二硒化物的叠氮硒基化反应，以及一系列相应的 β-叠氮基硒化物，其中大部分是新的在温和的反应条件下以中等至良好的收率制备了这些化合物。这种与烯烃加成的亲电子硒基化试剂的原位生成是立体有择的反加成，其以马尔科夫尼科夫取向发生。
• Electrophilic Azido Selenenylation of Alkenes. A Simple Synthetic Route to Racemic Taxol Side Chain
  作者：Marcello Tiecco、Lorenzo Testaferri、Andrea Temperini、Luana Bagnoli、Francesca Marini、Claudio Santi

  DOI：10.1080/00397919808007031

  日期：1998.6

  Simple alkenes react with PhSeOTf and NaN3 in MeCN to afford beta-phenylseleno azides as the result of a stereospecific trans addition. The regioselectivity of the process is determined by the structure of the alkene.
• Catalytic Chalcogenylation under Greener Conditions: A Solvent-Free Sulfur- and Seleno-functionalization of Olefins via I₂/DMSO Oxidant System
  作者：André A. Vieira、Juliano B. Azeredo、Marcelo Godoi、Claudio Santi、Eufrânio N. da Silva Júnior、Antonio L. Braga

  DOI：10.1021/jo502621a

  日期：2015.2.20

  Herein, we report a solvent- and metal-free methodology for the alkoxy-chalcogenylation of styrenes, using molecular iodine as a catalyst, DMSO as a stoichiometric oxidant, and different nucleophiles under microwave irradiation. This eco-friendly approach afforded the desired products in good to excellent yields in only 10 min. In addition, using the same protocol, we carried out the cyclization reaction of relevant molecules, such as lapachol derivatives.
• HASSNER, ALFRED;AMARASEKARA, ANANDA S., TETRAHEDRON LETT., 28,(1987) N 43, 5185-5188
  作者：HASSNER, ALFRED、AMARASEKARA, ANANDA S.

  DOI：——

  日期：——