4-ethynylbenzyl azide | 1097834-15-5

• 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-ethynylbenzyl azide
• 英文别名: 1-(azidomethyl)-4-ethynylbenzene
• CAS: 1097834-15-5
• 化学式: C₉H₇N₃
• 分子量: 157.175
• InChiKey: CTUFHQXXNYXBFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  4-ethynylbenzyl azide 在 lithium aluminium tetrahydride 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 7.0h， 生成 N²-p-ethynylbenzyl-2′-deoxyguanosine
  参考文献：
  名称：

  N2取代的2'-脱氧鸟苷三磷酸衍生物作为人类DNA聚合酶κ的选择性底物

  摘要：

  Ñ 2 -烷基-2'-脱氧鸟苷三磷酸（N 2 -烷基的dGTP）制备具有甲基，丁基，苄基，或4-乙炔基苄基取代基的衍生物和作为用于人DNA聚合酶的底物进行测试。N 2-苄基-dGTP等于dGTP作为DNA聚合酶κ（polκ）的底物，但对于polsβ，δ，η，ι或ν则是较差的底物。体内的反应性是通过N个孵化评价2 -4-乙炔基苄基-dG的用野生型和polκ缺陷型小鼠胚胎成纤维细胞。CuAAC与5（6）-FAM-叠氮化物的反应表明，只有含有polκ的细胞才能掺入N 2-4-乙炔基苄基-dG进入细胞核。这是Y家族聚合酶特异性dNTP的第一个实例，该方法可用于探测体内polκ的活性。

  DOI：

  10.1002/anie.201611607
• 作为产物：
  描述：

  4-ethynylbenzyl methanesulfonate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-ethynylbenzyl azide
  参考文献：
  名称：

  N2取代的2'-脱氧鸟苷三磷酸衍生物作为人类DNA聚合酶κ的选择性底物

  摘要：

  Ñ 2 -烷基-2'-脱氧鸟苷三磷酸（N 2 -烷基的dGTP）制备具有甲基，丁基，苄基，或4-乙炔基苄基取代基的衍生物和作为用于人DNA聚合酶的底物进行测试。N 2-苄基-dGTP等于dGTP作为DNA聚合酶κ（polκ）的底物，但对于polsβ，δ，η，ι或ν则是较差的底物。体内的反应性是通过N个孵化评价2 -4-乙炔基苄基-dG的用野生型和polκ缺陷型小鼠胚胎成纤维细胞。CuAAC与5（6）-FAM-叠氮化物的反应表明，只有含有polκ的细胞才能掺入N 2-4-乙炔基苄基-dG进入细胞核。这是Y家族聚合酶特异性dNTP的第一个实例，该方法可用于探测体内polκ的活性。

  DOI：

  10.1002/anie.201611607

文献信息

• Chemo- and Site-Selective Alkyl and Aryl Azide Reductions with Heterogeneous Nanoparticle Catalysts
  作者：Venkatareddy Udumula、S. Hadi Nazari、Scott R. Burt、Madher N. Alfindee、David J. Michaelis

  DOI：10.1021/acscatal.6b01217

  日期：2016.7.1

  to generating new leads for drug discovery. Herein, we show that heterogeneous nanoparticle catalysts enable site-selective monoreduction of polyazide substrates for the generation of aminoglycoside antibiotic derivatives. The nanoparticle catalysts are highly chemoselective for reduction of alkyl and aryl azides under mild conditions and in the presence of a variety of easily reduced functional groups

  生物活性天然产物的位点选择性修饰是产生用于药物发现的新线索的有效方法。在这里，我们表明，异质纳米颗粒催化剂能够实现聚叠氮化物底物的位点选择性单还原，以生成氨基糖苷类抗生素衍生物。纳米颗粒催化剂在温和条件下和在各种容易还原的官能团存在下对烷基和芳基叠氮化物的还原具有高度的化学选择性。已显示出用于单叠氮化物还原的高区域选择性有利于空间上受阻最小的叠氮化物的还原。我们假设观察到的选择性源自较少受阻的叠氮化物基团与纳米颗粒催化剂表面相互作用的更大能力。
• Catalytic Staudinger Reduction at Room Temperature
  作者：Danny C. Lenstra、Joris J. Wolf、Jasmin Mecinović

  DOI：10.1021/acs.joc.9b00831

  日期：2019.5.17

  catalytic Staudinger reduction at room temperature that enables the preparation of a structurally diverse set of amines from azides in excellent yields. The reaction is based on the use of catalytic amounts of triphenylphosphine as a phosphine source and diphenyldisiloxane as a reducing agent. Our catalytic Staudinger reduction exhibits a high chemoselectivity, as exemplified by reduction of azides

  我们报道了在室温下有效的Staudinger催化还原反应，该反应能够以优异的收率从叠氮化物制备结构多样的胺。该反应基于催化量的三苯基膦作为膦源和二苯基二硅氧烷作为还原剂的使用。我们的Staudinger催化还原具有很高的化学选择性，例如叠氮化物相对于其他常见官能团（包括腈，烯烃，炔烃，酯和酮）的还原。
• Weak Interactions Dominating the Supramolecular Self-Assembly in a Salt: A Designed Single-Crystal-to-Single-Crystal Topochemical Polymerization of a Terminal Aryldiacetylene
  作者：Zhong Li、Frank W. Fowler、Joseph W. Lauher

  DOI：10.1021/ja806663h

  日期：2009.1.21

  Single-crystal-to-single-crystal (SCSC) topochemical polymerizations of diacetylenes can yield nearly defect-free conjugated polymer crystals unattainable by other methods. Aryl-substituted diacetylenes with their potentially greater conjugation have been targeted for years, but until now no one has reported a SCSC polymerization of any aryl-substituted diacetylene. This is presumably due to the rigidity of such diaryl-substituted monomers as well as the lack of control over the supramolecular structure. To address this problem, the polymerization of a terminal phenyldiacetylene was targeted. It was assumed that a terminal diacetylene should demonstrate greater flexibility in the solid state. To establish the necessary (similar to 4.9 angstrom) repeat distance, commensurate with the repeat distance in the polymer, a host-guest system was designed. The chosen diacetylene guest, the amine DABzNH(2), was to be crystallized with the oxalamide dicarboxylic acid host, H(2)og. The plan required a segregation of the hydrogen bonds, amide-amide hydrogen bonds to establish the 4.9 angstrom spacing, and the carboxylate to ammonium ion hydrogen bonds to organize the guest. Prior to carrying out the diacetylene synthesis a series of model salts were studied. Consistent with the hydrophobic effect it was found that amines with large "greasy" substituents assembled according to the design. Once the model studies established that weak interactions could dominate the supramolecular structure of a salt, the actual design was put to the test. The targeted guest, DABzNH(2), was synthesized and crystals of the host-guest salt (DABzNH(3))(2)og were prepared. The resulting crystal structure was in complete accordance with the design. A SCSC polymerization was achieved by a slow annealing treatment lasting about three months. The crystal structure of the resulting polymer not only confirmed the first example of a poly (aryldiacetylene) single crystal, it also revealed an unexpected reaction pathway that shows a major movement involving the rigid aromatic substituent.
• Design and Synthesis of Dual-Action Inhibitors Targeting Histone Deacetylases and 3-Hydroxy-3-methylglutaryl Coenzyme A Reductase for Cancer Treatment
  作者：Jhih-Bin Chen、Ting-Rong Chern、Tzu-Tang Wei、Ching-Chow Chen、Jung-Hsin Lin、Jim-Min Fang

  DOI：10.1021/jm400179b

  日期：2013.5.9

  A series of dual-action compounds were designed to target histone deacetylase (HDAC) and 3-hydroxy-3-methylglutaryl coenzyme A reductase (HMGR) by having a hydroxamate group essential for chelation with the zinc ion in the active site of HDAC and the key structural elements of statin for binding with both proteins. In our study, the statin hydroxamic acids prepared by a fused strategy are most promising in cancer treatments. These compounds showed potent inhibitory activities against HDACs and HMGR with IC50 values in the nanomolar range. These compounds also effectively reduced the HMGR activity as well as promoted the acetylations of histone and tubulin in cancer cells, but were not toxic to normal cells.