4-Azido-2,2-diphenylbutyronitrile | 147609-07-2

• 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: 4-Azido-2,2-diphenylbutyronitrile
• 英文别名: 4-azido-2,2-diphenylbutanenitrile
• CAS: 147609-07-2
• 化学式: C₁₆H₁₄N₄
• 分子量: 262.314
• InChiKey: UWFGUWIHGGETNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Azido-2,2-diphenylbutyronitrile 在 三乙基硅烷 、 indium(III) chloride 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 3,3-二苯基-2-吡咯烷亚胺
  参考文献：
  名称：

  Reaction of Azides with Dichloroindium Hydride:  Very Mild Production of Amines and Pyrrolidin-2-imines through Possible Indium−Aminyl Radicals

  摘要：

  Organic azides are easily reduced to the corresponding amines by reaction with dichloroindium hydride under very mild conditions and in a highly chemoselective fashion. gamma-Azidonitriles give rise to outstanding five-membered cyclizations affording pyrrolidin-2-imines. A rationalization of the overall experimental data cannot exclude the occurrence of competitive radical and nonradical pathways, but certain results are, however, soundly consistent with the intermediacy of indium-bound nitrogen-centered radicals.

  DOI：

  10.1021/ol0606637
• 作为产物：
  描述：

  溴乙基二苯乙腈 在 sodium azide 作用下， 生成 4-Azido-2,2-diphenylbutyronitrile
  参考文献：
  名称：

  L'abbe, Gerrit; Sannen, Ingrid; Dehaen, Wim, Journal of the Chemical Society. Perkin transactions I, 1993, # 1, p. 27 - 30

  摘要：

  DOI：

文献信息

• A Potent and Highly Selective Inhibitor of Human α-1,3-Fucosyltransferase via Click Chemistry
  作者：Lac V. Lee、Michael L. Mitchell、Shih-Jung Huang、Valery V. Fokin、K. Barry Sharpless、Chi-Huey Wong

  DOI：10.1021/ja0302836

  日期：2003.8.1

  Potent inhibitors of fucosyltransferases, and glycosyltransferases in general, have been elusive due to the inherent barriers surrounding the family of glycosyltransfer reactions. The problems of weak substrate affinity and low catalytic proficiency of fucosyltransferase was offset by recruiting additional binding features, in this case hydrophobic interactions, to produce a high affinity inhibitor

  由于围绕糖基转移反应家族的固有障碍，岩藻糖基转移酶和糖基转移酶的强效抑制剂一直难以捉摸。底物亲和力弱和岩藻糖基转移酶催化效率低的问题通过招募额外的结合特征（在这种情况下为疏水相互作用）来产生高亲和力抑制剂 24，Ki = 62 nM 得到了抵消。该分子是从包含 85 种化合物的 GDP-三唑文库中鉴定出来的，这些化合物是通过 Cu(I) 催化的叠氮化物和乙炔反应物之间的 [2 + 3] 环加成反应产生的，然后在没有产物分离的情况下进行原位筛选。
• Modular assembly of azo photo-switches using click chemistry allows for predictable photo-behaviour
  作者：Alexis Goulet-Hanssens、Christopher J. Barrett

  DOI：10.1016/j.jphotochem.2014.07.013

  日期：2014.11

  Many azobenzene-based applications rely on variations in the 'head' group of the chromophores. We present a method to chemically modify azobenzenes quickly and easily, and report the effects that these modifications have on the properties of the azobenzene chromophores. Using now common 'click' chemistry, we have developed a methodology which can be applied in a one-pot fashion to rapidly vary the molecular structure, permitting the synthesis of libraries of dyes while allowing for the retention of photophysical characteristics. We validate this synthetic approach as not changing the nature of the chromophores in our testing of 17 derivatives, indicating that this is a good strategy for easy and rapid molecular tailoring. The results of this study will facilitate the use of these versatile molecules in material science, as it renders diverse structures attainable within one day instead of standard, multi-day syntheses per chromophore. (C) 2014 Elsevier B.V. All rights reserved.
• L'abbe, Gerrit; Sannen, Ingrid; Dehaen, Wim, Journal of the Chemical Society. Perkin transactions I, 1993, # 1, p. 27 - 30
  作者：L'abbe, Gerrit、Sannen, Ingrid、Dehaen, Wim

  DOI：——

  日期：——
• Reaction of Azides with Dichloroindium Hydride:  Very Mild Production of Amines and Pyrrolidin-2-imines through Possible Indium−Aminyl Radicals
  作者：Luisa Benati、Giorgio Bencivenni、Rino Leardini、Daniele Nanni、Matteo Minozzi、Piero Spagnolo、Rosanna Scialpi、Giuseppe Zanardi

  DOI：10.1021/ol0606637

  日期：2006.6.1

  Organic azides are easily reduced to the corresponding amines by reaction with dichloroindium hydride under very mild conditions and in a highly chemoselective fashion. gamma-Azidonitriles give rise to outstanding five-membered cyclizations affording pyrrolidin-2-imines. A rationalization of the overall experimental data cannot exclude the occurrence of competitive radical and nonradical pathways, but certain results are, however, soundly consistent with the intermediacy of indium-bound nitrogen-centered radicals.