2-(azidomethyl)-1H-indole | 1333393-75-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-(azidomethyl)-1H-indole
• CAS: 1333393-75-1
• 化学式: C₉H₈N₄
• 分子量: 172.189
• InChiKey: NERPBYWWELPMQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  30.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(azidomethyl)-1H-indole 在 4-二甲氨基吡啶 、 (IPr)Au(NTf₂) 、 silver(I) acetate 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 45.0h， 生成 tert-butyl 3-(N-(4-methoxyphenyl)methylsulfonamido)-4-phenyl-9H-pyrido-[3,4-b]indole-9-carboxylate
  参考文献：
  名称：

  Generation of α-Imino Gold Carbenes through Gold-Catalyzed Intermolecular Reaction of Azides with Ynamides

  摘要：

  The generation of a-imino gold carbenes via gold-catalyzed intermolecular reaction of azides and ynamides is disclosed. This new methodology allows for highly regioselective access to valuable 2,aminoindoles and 3-amino-beta-carbolines in generally good to excellent yields. A mechanistic rationale for this tandem reaction, especially for the observed high regioselectivity, is supported by DFT calculations.

  DOI：

  10.1021/jacs.5b06015
• 作为产物：
  描述：

  1H-吲哚-2-甲醛 在 甲醇 、 sodium tetrahydroborate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 13.17h， 生成 2-(azidomethyl)-1H-indole
  参考文献：
  名称：

  Subtle Structural Changes across the Boundary between A2AR/A2BR Dual Antagonism and A2BR Antagonism: A Novel Class of 2-Aminopyrimidine-Based Derivatives

  摘要：

  DOI：

  10.1021/acs.jmedchem.4c00250

文献信息

• 三唑并四氢-β-咔啉衍生物及其制备方法和应用
  申请人：皖南医学院

  公开号：CN113024553B

  公开（公告）日：2022-02-25

  本发明提供了三唑并四氢‑β‑咔啉衍生物及其制备方法和应用，将取代的2‑吲哚甲基叠氮、取代的炔丙醇和催化剂混合在有机溶剂中，加热反应，反应结束后，纯化分离，即得三唑并四氢‑β‑咔啉衍生物。本发明利用取代的吲哚甲基叠氮与取代炔丙醇串联反应来制备三唑并四氢‑β‑咔啉衍生物，具有反应步骤少，产率高的优点，而且所得三唑并四氢‑β‑咔啉衍生物具有良好的抑菌性能。
• Synthesis of tetrahydro-β-carbolines from 2-indolylmethyl azides and propargylic alcohols
  作者：Haiting Yin、Qin Ma、Yushan Wang、Xiaoxia Gu、Zhijun Feng、Yunjun Wu、Ming Wang、Shaoyin Wang

  DOI：10.1039/d1ra03022a

  日期：——

  A facile and efficient route to tetrahydro-β-carbolines from 2-indolylmethyl azides and propargylic alcohols via acid-catalyzed dehydrative annulation reactions is described. This reaction proceeds through a cascade sequence of Friedel–Crafts-type alkylation followed by intramolecular “Click” reaction, involving the formation of multiple chemical bonds in a single operation with excellent atom-economy

  描述了一种通过酸催化脱水环化反应从 2-吲哚甲基叠氮化物和炔丙醇制备四氢-β-咔啉的简便有效途径。该反应通过傅克式烷基化的级联顺序进行，然后是分子内“点击”反应，涉及在一次操作中形成多个化学键，具有优异的原子经济性和广泛的官能团耐受性。
• Lewis Acid Catalyzed [4 + 3] Cycloaddition of Propargylic Alcohols with Azides
  作者：Ya-Ping Han、Xian-Rong Song、Yi-Feng Qiu、Heng-Rui Zhang、Lian-Hua Li、Dong-Po Jin、Xiao-Qing Sun、Xue-Yuan Liu、Yong-Min Liang

  DOI：10.1021/acs.orglett.5b03657

  日期：2016.3.4

  An unprecedented Lewis acid catalyzed [4 + 3] cycloaddition reaction is described that provides a straightforward route to polycyclic products containing an imine-based indole azepine scaffold, starting from readily available internal tertiary alkynols and azides. This cycloaddition protocol provides efficient and atom-economical access to a new class of fascinating imine-containing products in satisfactory

  描述了前所未有的路易斯酸催化的[4 + 3]环加成反应，从容易获得的内部叔炔醇和叠氮化物开始，它提供了一种直接的途径来制备包含亚胺基吲哚氮杂骨架的多环产物。该环加成方案以令人满意的产率提供了有效且原子经济的途径来获得新型的令人着迷的含亚胺的产物，这已在七元N杂环的构建中显示出良好的应用。
• Rapid and Mild Nucleophilic Substitution of a Highly Active (Indol-2-yl)methyl Electrophile in a Microflow Reactor
  作者：Shinichiro Fuse、Yuma Matsuura、Naoto Yamasaki

  DOI：10.1055/s-0043-1775370

  日期：2024.9

  frequently used chemical reaction in the pharmaceutical field. Developing protocols for the nucleophilic substitution of (indol-2-yl)methyl electrophiles is important for functionalizing indoles. There are few studies on the nucleophilic substitution at the 2′-position of the electrophiles without an electron-withdrawing group at the 1-position or substituents at the 2′- and 3-positions, where the existing

  吲哚是功能性农业和药物分子中的常见基序。杂原子烷基化是制药领域最常用的化学反应。开发（吲哚-2-基）甲基亲电子试剂的亲核取代方案对于吲哚功能化非常重要。对于1位无吸电子基团或2′位和3位取代基的亲电试剂2′位亲核取代的研究较少，现有方法需要高温和长时间反应次。在本研究中，我们证明了吲哚衍生物 2' 位上的快速（7-12 s）和温和（25 °C）微流亲核取代，1 位没有吸电子基团， 2'- 位没有取代基。或 3 位。类似的批次条件导致产率较低。
• Synthesis and biochemical evaluation of triazole/tetrazole-containing sulfonamides against thrombin and related serine proteases
  作者：Rogelio Siles、Yuko Kawasaki、Patrick Ross、Ernesto Freire

  DOI：10.1016/j.bmcl.2011.07.023

  日期：2011.9

  A small library of 25 triazole/tetrazole-based sulfonamides have been synthesized and further evaluated for their inhibitory activity against thrombin, trypsin, tryptase and chymase. In general, the triazole-based sulfonamides inhibited thrombin more efficiently than the tetrazole counterparts. Particularly, compound 26 showed strong thrombin inhibition (K-i = 880 nM) and significant selectivity against other human related serine proteases like trypsin (K-i = 729 mu M). Thrombin binding affinity of the same compound was determined by ITC and demonstrated that the binding of this new triazole-based scaffold is enthalpically driven, making it a good candidate for further development. (C) 2011 Elsevier Ltd. All rights reserved.