[(叠氮甲氧基)甲基]苯 | 52827-28-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: [(叠氮甲氧基)甲基]苯
• 英文名称: [(azidomethoxy)methyl]benzene
• 英文别名: Benzene, (azidomethoxymethyl)-；azidomethoxymethylbenzene
• CAS: 52827-28-8
• 化学式: C₈H₉N₃O
• 分子量: 163.179
• InChiKey: IMRXSEKBRIGHNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  丙炔酸 、 [(叠氮甲氧基)甲基]苯 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 以88%的产率得到1-(Phenylmethoxymethyl)triazole-4-carboxylic acid
  参考文献：
  名称：

  A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes

  摘要：

  DOI：

  10.1002/1521-3773(20020715)41:14<2596::aid-anie2596>3.0.co;2-4
• 作为产物：
  描述：

  苄基氯甲基醚 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 生成 [(叠氮甲氧基)甲基]苯
  参考文献：
  名称：

  Efficient Synthesis of 2-Substituted-1,2,3-triazoles

  摘要：

  In this three-component reaction, alkynes undergo a copper(I)-catalyzed cycloaddition with sodium azide and formaldehyde to yield 2-hydroxymethyl-2H-1,2,3-triazoles, which are useful intermediates that can be readily converted to polyfunctional molecules. The hydroxymethyl group can also be removed, providing convenient access to NH-1,2,3-triazoles. The reaction is experimentally simple and readily scalable.

  DOI：

  10.1021/ol8006748

文献信息

• [EN] GLUCOSE TRANSPORT INHIBITORS<br/>[FR] INHIBITEURS DE TRANSPORT DU GLUCOSE
  申请人：BAYER PHARMA AG

  公开号：WO2016202898A1

  公开（公告）日：2016-12-22

  The present invention relates to chemical compounds that selectively inhibit glucose transporter 1 (GLUT1), to methods of preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds, to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, as well as to intermediate compounds useful in the preparation of said compounds.

  本发明涉及选择性抑制葡萄糖转运蛋白1（GLUT1）的化合物，涉及制备该类化合物的方法，涉及包含该类化合物的药物组合物和药物组合物，涉及利用该类化合物制造用于治疗或预防疾病的药物组合物，以及用于制备该类化合物的中间化合物。
• Double [3 + 2]-dimerisation cascade synthesis of bis(triazolyl)bisphosphanes, a new scaffold for bidentate bisphosphanes
  作者：Coralie Laborde、Muh-Mei Wei、Arie van der Lee、Eric Deydier、Jean-Claude Daran、Jean-Noël Volle、Rinaldo Poli、Jean-Luc Pirat、Eric Manoury、David Virieux

  DOI：10.1039/c5dt02197a

  日期：——

  Highly convergent synthesis of bis(triazolylphosphane oxides) by a tandem copper-mediated Huisgen reaction–oxidative coupling.

  通过串联铜介导的Huisgen反应-氧化偶联高度收敛合成双三唑基膦氧化物。
• N6-substituted adenosines. Cytokinin and antitumor activities
  作者：Svetlana V. Kolyachkina、Vitali I. Tararov、Cyril S. Alexeev、Dmitry M. Krivosheev、Georgy A. Romanov、Evgenia V. Stepanova、Eliso S. Solomko、Andrey N. Inshakov、Sergey N. Mikhailov

  DOI：10.1135/cccc2011114

  日期：——

  A series of N⁶-adenosine derivatives were synthesized by alkylation of N⁶-acetyl-2′,3′,5′-tri-O-acetyladenosine (1) with alkyl halides and alcohols. It was shown that propargyl derivative 2a is a good substrate for copper(I) catalyzed Huisgen [3+2] cycloaddition with azides. This click-reaction can be used for preparation of the libraries of 1,2,3-triazolyl modified adenosines. Biological activities of N⁶-adenosines were studied in two plant and six human cancer cell assays. The remarkable parallel between cytokinin and cytotoxic activities was found. The most cytokinin active compounds 3c–3e at the same time appeared to be the most potent cytotoxic agents.

  一系列的N6-腺苷衍生物通过烷基卤化物和醇对N6-乙酰-2'，3'，5'-三-O-乙酰基腺苷（1）进行烷基化合成。结果表明，丙炔基衍生物2a是铜（I）催化的Huisgen [3+2]环加成与叠氮化物反应的良好底物。此点击反应可用于制备1,2,3-三唑基修饰的腺苷库。在两种植物和六种人类癌细胞测试中研究了N6-腺苷的生物活性。发现细胞分裂素和细胞毒性活性之间存在显著的平行关系。同时，最具细胞分裂素活性的化合物3c-3e也被证明是最有效的细胞毒性剂。
• Debenzylation of Functionalized 4- and 5-Substituted 1,2,3-Triazoles
  作者：Leiv Sydnes、Bengt Haug、Tahir Farooq、Karl Törnroos

  DOI：10.1055/s-0031-1291160

  日期：2012.7

  A range of 4- and 5-substituted N-benzyl-1,2,3-triazoles have been submitted to debenzylation using Pd/C and hydrogen in the presence of 1,1,2-trichloroethane. Triazoles with oxygen-containing substituents are efficiently debenzylated under these conditions. Triazoles with a phenyl or benzyl substituent on C4 or C5 are not debenzylated, whereas a pentyl-substituted derivative was readily debenzylated.
• Direct Synthesis of 1,5-Disubstituted-4-magnesio-1,2,3-triazoles, Revisited
  作者：Antoni Krasiński、Valery V. Fokin、K. Barry Sharpless

  DOI：10.1021/ol0499203

  日期：2004.4.1

  [GRAPHICS]After revisiting earlier works reporting the regioselective synthesis of 1,5-disubstituted-1,2,3-triazoles via the addition of bromomagnesium acetylides to azides, much improved yields of the products were obtained for a wide array of azides and alkynes. The intermediates of that reaction can be trapped with different electrophiles to regioselectively form 1,4,5-trisubstituted 1,2,3-triazoles.