1-(叠氮甲基)-2-(三氟甲基)苯 | 823189-03-3

• 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: 1-(叠氮甲基)-2-(三氟甲基)苯
• 英文名称: 2-trifluoromethylbenzylazide
• 英文别名: 1-(azidomethyl)-2-(trifluoromethyl)benzene
• CAS: 823189-03-3
• 化学式: C₈H₆F₃N₃
• 分子量: 201.151
• InChiKey: DISKVNRGMSADDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(叠氮甲基)-2-(三氟甲基)苯 在 sodium ethanolate 、 N,N-二乙基苯胺 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 7-Chloro-5-phenyl-3-(2-trifluoromethyl-benzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine
  参考文献：
  名称：

  Synthesis, biological activity and molecular modelling of new trisubstituted 8-azaadenines with high affinity for A1 adenosine receptors

  摘要：

  We describe here the synthesis and biological activity of new 8-azaadenines bearing both a phenyl group on C(2) and a 9-benzyl group substituted in the ortho position with a Cl or a F atom or a CF3 group, to verify the synergistic effect of a combination of these substitution patterns on binding with the A(1) adenosine receptors. In position N-6 aliphatic and cycloaliphatic substituents were chosen which had been shown to bind well with the A(1) receptors. Because of the high lipophilicity of these kinds of molecules, we also introduced a hydroxyalkyl substituent in the same position. The compounds obtained generally showed a very good affinity and selectivity for A(1) receptors. Some of the compounds showed K-i in the nanomolar range, one even in the subnanomolar range (0.6 nM). Molecular docking calculations were performed in order to evaluate the interaction energies between the bovine A(1) receptor model and the selected ligands, and then to correlate these energies with biological activities of the ligands as obtained from the experiments. Molecular docking analysis suggests different binding modes towards A(1) receptors that are plausible for these ligands. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.08.014
• 作为产物：
  描述：

  2-(三氟甲基)苄溴 在 sodium azide 作用下， 以 水 为溶剂， 生成 1-(叠氮甲基)-2-(三氟甲基)苯
  参考文献：
  名称：

  Palladium-catalyzed cross-coupling reaction of azides with isocyanides

  摘要：

  一种钯催化的偶联反应方法已经开发出来，可以将叠氮化合物与异氰酸酯进行偶联，从而提供了一种合成非对称碳二亚胺的通用途径。

  DOI：

  10.1039/c5cc05981j

文献信息

• Highly regioselective and sustainable solar click reaction: a new post-synthetic modified triazole organic polymer as a recyclable photocatalyst for regioselective azide–alkyne cycloaddition reaction
  作者：Dolly Yadav、Nem Singh、Tae Wu Kim、Jae Young Kim、No-Joong Park、Jin-Ook Baeg

  DOI：10.1039/c9gc00894b

  日期：——

  and regioselectivity. The reaction was studied for a series of substrates and the absolute regioselectivity of a representative triazole product has also been confirmed by X-ray crystallography. The proficiency and chemical orthogonality of the Ni-TLOP are remarkable and it shows enhanced efficiency and regioselectivity. The use of a recyclable photocatalyst and non-hazardous reagents makes the catalytic

  在寻找独特而有效的催化剂以使该过程高效，绿色和可持续的过程中，对药用活性1,2,3-三唑的合成一直进行了严格的审查。在这里，我们提出了一种新的可见光活性镍（II）Cyclam集成的三唑连接的有机聚合物（Ni-TLOP）光催化剂，具有出色的效率和区域选择性，可合成1,2,3-三唑化合物。研究了一系列底物的反应，并且还通过X射线晶体学证实了代表性三唑产物的绝对区域选择性。Ni-TLOP的熟练度和化学正交性非常出色，并且显示出更高的效率和区域选择性。可循环使用的光催化剂和非危险试剂的使用使催化系统具有可持续性和环境友好性。这种光催化的点击反应技术已成功应用于最畅销的抗癫痫药rufinamide的合成。
• 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。
• Palladium-catalyzed cross-coupling reaction of azides with isocyanides
  作者：Zhen Zhang、Zongyang Li、Bin Fu、Zhenhua Zhang

  DOI：10.1039/c5cc05981j

  日期：——

  A palladium-catalyzed cross-coupling reaction of azides with isocyanides is developed, providing a general synthetic route to unsymmetric carbodiimides.

  一种钯催化的偶联反应方法已经开发出来，可以将叠氮化合物与异氰酸酯进行偶联，从而提供了一种合成非对称碳二亚胺的通用途径。
• Discovery of 7-Methyl-10-Hydroxyhomocamptothecins with 1,2,3-Triazole Moiety as Potent Topoisomerase I Inhibitors
  作者：Xiguo Xu、Yuelin Wu、Wenfeng Liu、Chuanquan Sheng、Jianzhong Yao、Guoqiang Dong、Kun Fang、Jin Li、Zhiliang Yu、Xiao Min、Huojun Zhang、Zhenyuan Miao、Wannian Zhang

  DOI：10.1111/cbdd.12767

  日期：2016.9

  Homocamptothecin is emerging as an important topoisomerase I inhibitor originating in natural product camptothecin. We report the modifications and SAR of homocamptothecin on position C10 to develop potent topoisomerase I inhibitors for anticancer drug discovery. Based on click chemistry, twenty‐one 1,2,3‐triazole‐substituted homocamptothecin derivatives were readily synthesized in two steps. For A549

  喜树碱是一种重要的拓扑异构酶I抑制剂，起源于喜树碱天然产物。我们报道了C10位置上喜树碱的修饰和SAR，以开发有效的拓扑异构酶I抑制剂用于抗癌药物的发现。根据点击化学，可以很容易地通过两个步骤合成二十一种1,2,3-三唑取代的同型喜树碱衍生物。对于A549，环烷基和烷基取代的化合物6j，6l和6o表现出高度的抗增殖抑制活性，IC 50值分别为30、30和50 n m。此外，环丙基6j的Topo I抑制活性高于20（S）喜树碱，表明适合进一步药物开发。
• Design, synthesis, biological evaluation and molecular docking study of novel pyridoxine–triazoles as anti-Alzheimer's agents
  作者：Tiyas Pal、Saipriyanka Bhimaneni、Abha Sharma、S. J. S. Flora

  DOI：10.1039/d0ra04942e

  日期：——

  derivatives were designed, synthesized, characterized and evaluated as anti-Alzheimer agents. In vitro testing revealed the multi-functional properties of compounds such as inhibition of acetylcholinesterase (AChE), antioxidant and metal chelation. Among the series, 5i derivative was found most potent AChE inhibitor, possess antioxidant potential and chelating metal ions. Further binding interaction of 5i with

  设计、合成、表征和评估了一系列多靶点天然产物吡哆醇基衍生物作为抗阿尔茨海默病药物。体外测试揭示了化合物的多功能特性，例如抑制乙酰胆碱酯酶 (AChE)、抗氧化剂和金属螯合。在该系列中，5i衍生物被发现是最有效的AChE抑制剂，具有抗氧化能力和螯合金属离子。使用分子对接研究了5i与 AChE的进一步结合相互作用，显示与 AChE 的 PAS 和 CAS 位点的相互作用。还进行了计算机预测以预测分子 5i 的毒性和ADME特性并在药物相似范围内发现。因此，5i可能是一种很有前途的多功能化合物，可用于进一步开发治疗阿尔茨海默病的新药。