2-azido-1-phenyl-1-(phenylseleno)ethane | 116316-13-3

• 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-1-phenyl-1-(phenylseleno)ethane
• 英文别名: (2-Azido-1-phenylethyl)selanylbenzene
• CAS: 116316-13-3
• 化学式: C₁₄H₁₃N₃Se
• 分子量: 302.237
• InChiKey: OGQVZRBGSCPGMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 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-1-phenyl-1-(phenylseleno)ethane 在 盐酸 、 copper(l) iodide 、 水 、 三乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 10.0h， 生成 苯亚硒酸
  参考文献：
  名称：

  2-Azido-1-Phenyl-1-(Phenylseleno)Ethane 通过顺序点击消除反应一锅法合成 1-(E)-Phenylethenyl-1,2,3-Triazoles

  摘要：

  摘要 一种新的方便的一锅两步法，包括顺序点击化学和氧化消除反应，用于从 2-叠氮基制备带有 1-(E)-苯基乙烯基的 1,4-二取代 1,2,3-三唑。描述了-1-苯基-1-(苯基硒基)乙烷。该协议的突出特点是反应条件温和、操作简单、产品收率高、避免了硒化中间体的分离。补充材料可用于本文。有关以下免费补充文件，请转至出版商在线版的磷、硫和硅及相关元素：附加数据。图形概要

  DOI：

  10.1080/10426507.2013.769987
• 作为产物：
  描述：

  苯乙烯 、 二苯基二硒醚 在 sodium azide 、 Ph(OAc)2 作用下， 以 二氯甲烷 为溶剂， 生成 2-azido-1-phenyl-1-(phenylseleno)ethane
  参考文献：
  名称：

  苯甲烯基三氟甲磺酸酯促进的分子内亲核去硒烯化反应。邻氨基氨基醇前体的立体定向合成。

  摘要：

  用亲电子亚硒化剂活化后，邻位叠氮基硒化物的苯基硒基含有内部的氧或氮亲核取代基，容易发生分子内亲核取代，得到叠氮基取代的杂环化合物。这种分子内取代发生在带有硒原子的碳原子上的构型反转的情况下。从乙酰氨基硒化物和氨基甲酸酯硒化物开始，已经开发了邻位氨基醇前体恶唑啉和恶唑烷-2-酮的立体控制合成。

  DOI：

  10.1021/jo960866g

文献信息

• Selenoxide Elimination Triggers Enamine Hydrolysis to Primary and Secondary Amines: A Combined Experimental and Theoretical Investigation
  作者：Giovanni Ribaudo、Marco Bortoli、Erika Oselladore、Alberto Ongaro、Alessandra Gianoncelli、Giuseppe Zagotto、Laura Orian

  DOI：10.3390/molecules26092770

  日期：——

  We discuss a novel selenium-based reaction mechanism consisting in a selenoxide elimination-triggered enamine hydrolysis. This one-pot model reaction was studied for a set of substrates. Under oxidative conditions, we observed and characterized the formation of primary and secondary amines as elimination products of such compounds, paving the way for a novel strategy to selectively release bioactive

  我们讨论了一种新颖的基于硒的反应机制，其中包括氧化硒消除引发的烯胺水解。针对一组底物研究了这种一锅模型反应。在氧化条件下，我们观察并表征了伯胺和仲胺作为此类化合物消除产物的形成，为选择性释放生物活性分子的新策略铺平了道路。使用核磁共振、质谱和密度泛函理论（DFT）研究了其潜在机制。
• Substituted azides from selenium-promoted deselenenylation of azido selenides. Glycosylation reactions of protected 2-azido-2-deoxy-1-selenoglycopyranoses
  作者：Marco Tingoli、Marcello Tiecco、Lorenzo Testaferri、Andrea Temperini

  DOI：10.1039/c39940001883

  日期：——

  After activation with electrophilic selenenylating agents, the phenylseleno group of vicinal azido selenides can be easily substituted by nucleophiles to afford a variety of substituted azides.

  经过电亲核硒烷基化剂的活化，邻位叠氮硒化物的苯基硒基团可以很容易被亲核试剂替代，从而获得多种取代的叠氮化合物。
• 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。
• Novel azido-phenylselenenylation of double bonds. Evidence for a free-radical process
  作者：Marco Tingoli、Marcello Tiecco、Donatella Chianelli、Roberta Balducci、Andrea Temperini

  DOI：10.1021/jo00024a020

  日期：1991.11

  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.
• Homogeneous azidophenylselenylation of glycals using TMSN3–Ph2Se2–PhI(OAc)2
  作者：Yuri V. Mironov、Andrei A. Sherman、Nikolay E. Nifantiev

  DOI：10.1016/j.tetlet.2004.10.022

  日期：2004.11

  An improved preparative method for homogeneous azidophenylselenylation of glycals is described consisting of reaction with TMSN3 and Ph2Se2 in the presence of Phl(OAc)(2). The Use of TMSN3 instead of NaN3 as in the heterogeneous procedure, allowed both a reduced reaction time and a scale-Lip that was not possible in the case of the azidophenylselenylation of substituted glycals using NaN3. (C) 2004 Elsevier Ltd. All rights reserved.