1-(1-adamantyl)-1,2,4-triazole | 69625-62-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(1-adamantyl)-1,2,4-triazole
• 英文别名: 1H-1,2,4-Triazole, 1-tricyclo(3.3.1.13,7)dec-1-yl-
• CAS: 69625-62-3
• 化学式: C₁₂H₁₇N₃
• 分子量: 203.287
• InChiKey: ZBBZETXZKFHHLA-UHFFFAOYSA-N

物化性质

• 熔点：
  81-82 °C
• 沸点：
  344.4±25.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(1-adamantyl)-1,2,4-triazole 在 硫酸 、 硝酸 、 甲酸 、 水 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以70%的产率得到1-(1,2,4-triazol-1-yl)-3-hydroxyadamantane
  参考文献：
  名称：

  唑基取代金刚烷衍生物及其配位化合物的合成

  摘要：

  研究了金刚烷基唑与亲核试剂（水、一氧化碳、乙腈）在硫酸中的反应。合成了含有一个杂环取代基和一个羟基或乙酰胺取代基的新型双功能金刚烷衍生物。合成了铜(II)和锌(II)与1-金刚烷基-1,2,4-三唑、4-金刚烷基吡唑和4-金刚烷基-3,5-二甲基吡唑的配位化合物并对其进行了结构表征。这些配合物是唑基金刚烷配位化合物的第一个例子。

  DOI：

  10.1007/s11172-020-2985-2
• 作为产物：
  描述：

  1-金刚烷醇 在 吡啶 、 偶氮二甲酸二异丙酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 生成 1-(1-adamantyl)-1,2,4-triazole
  参考文献：
  名称：

  烷基亚膦酸盐作为稳定碳阳离子的合成子

  摘要：

  我们提出了一种基于氧化还原缩合反应的无酸生成碳正离子的新方法，该反应能够与各种亲核试剂发生S N 1 反应。我们利用容易合成的亚膦酸盐，这些亚膦酸盐被偶氮二甲酸二异丙酯活化，形成甜菜碱结构，该结构在添加亲核试剂后坍塌，从而产生反应性碳阳离子中间体。我们还采用这种方法对一些生物活性分子进行烷基化。

  DOI：

  10.1021/acs.orglett.2c00042

文献信息

• Synthesis of adamantane derivatives. LVIII. Reaction of 1-adamantyl chloride with some heterocyclic unsaturated silanes.
  作者：TADASHI SASAKI、AKIRA NAKANISHI、MASATOMI OHNO

  DOI：10.1248/cpb.30.2051

  日期：——

  Various silylated heterocycles having amide functionality were treated with 1-adamantyl chloride (1) in the presence of a Lewis acid to give the corresponding N-adamantylated heterocycles. If α-position to the reacting lactim nitrogen was substituted, the reaction no longer occurred, or the adamantylation occurred at the position other than the expected nitrogen. These facts are attributed to a steric blocking effect of the α-substituent. While the same treatment of the thioamide 46 gave the S-adamantylated product, 48 and 51 afforded in contrast the N- and S-adamantylated products, respectively ; this result can be explained in terms of steric effect. Analogously, silylated 2-pyrazolines and triazoles were adamantylated at nitrogen. The reactions of 2-trimethylsilylthiophene, furan and -pyridine with 1 failed to give site-selective monoadamantylation.

  在路易斯酸存在下，用 1-金刚烷酰氯（1）处理各种具有酰胺官能团的硅烷化杂环，得到相应的 N-金刚烷化杂环。如果反应的内酰胺氮的α位被取代，则不再发生反应，或者在预期氮以外的位置发生金刚烷基化反应。这些情况都归因于 α 取代基的立体阻滞效应。同样处理硫代酰胺 46 得到的是 S-金刚烷化产物，而 48 和 51 则分别得到了 N-和 S-金刚烷化产物；这一结果可以用立体效应来解释。类似地，硅烷化的 2-吡唑和三唑也在氮处发生了金刚烷化。2-三甲基硅基噻吩、呋喃和吡啶与 1 的反应未能产生位点选择性的单金刚烷化反应。
• METHODS OF USE OF ANTIVIRAL COMPOUNDS
  申请人：Wang Jizhou

  公开号：US20110065766A1

  公开（公告）日：2011-03-17

  The present invention relates, in part, to methods of treatment, prevention, and inhibition of viral disorders. In one aspect, the present invention relates to inhibition of the M2 proton channel of influenza viruses (e.g. influenza A virus) and other similar viroporins (e.g., VP24 of Ebola and Marburg viruses; and NS3 protein of Bluetongue). The present invention further relates, inter alia, to compounds which have been shown to possess antiviral activity, in particular, inhibiting the M2 proton channel of influenza viruses.

  本发明涉及部分治疗、预防和抑制病毒性疾病的方法。在一个方面，本发明涉及抑制流感病毒（例如流感A病毒）和其他类似的病毒孔蛋白（例如埃博拉和马尔堡病毒的VP24；以及蓝舌病的NS3蛋白）的M2质子通道。本发明还涉及已被证明具有抗病毒活性的化合物，特别是抑制流感病毒M2质子通道的化合物。
• Synthesis, crystal structures, and luminescence properties of coordination polymers and a discrete complex of cadmium(ii) halides with 1-(1,2,4-triazol-1-yl)adamantane
  作者：D. I. Pavlov、A. A. Ryadun、D. G. Samsonenko、V. P. Fedin、A. S. Potapov

  DOI：10.1007/s11172-021-3159-6

  日期：2021.5

  with cadmium(ii) chloride, bromide, and iodide were studied. The crystal structures of the synthesized coordination compounds were determined by single-crystal X-ray diffraction. Cadmium(ii) chloride and bromide form 1D coordination polymers, in which cadmium ions are bridged by two halide ions, whereas cadmium(ii) iodide forms a discrete complex with a tetrahedral environment of the cadmium ion. in

  研究了 1-(1,2,4-triazol-1-yl)adamantane 与氯化镉 ( ii )、溴化物和碘化物的反应。合成的配位化合物的晶体结构通过单晶 X 射线衍射确定。氯化镉 ( ii ) 和溴化物形成一维配位聚合物，其中镉离子由两个卤化物离子桥接，而镉 ( ii)) 碘化物与镉离子的四面体环境形成离散的复合物。在所有化合物中，有机配体以单齿方式通过 1,2,4-三唑环的 4 个位置的氮原子配位。卤化物配合物的配体中心发光量子产率在从氯到碘的一系列卤素中增加，碘化物配合物达到35％。
• Solvent-free and direct C(sp3)–H amination of adamantanes by grinding
  作者：Zhen Wei、Jiarong Li、Ning Wang、Qi Zhang、Daxin Shi、Kening Sun

  DOI：10.1016/j.tet.2014.01.014

  日期：2014.2

  A facile, direct and environmentally benign conversion of C(sp(3))-H bonds to C(sp(3))-N bonds using substoichiometric amount of aprotic superelectrophiles polyhalomethane-AIX(3) has been achieved by grinding under solvent-free conditions at room temperature in air. It is a general and simple method for the direct amination of adamantanes, and a series of aminoadamantanes of azoles, arylamines or heteroarylamines were obtained in good to excellent yields. The advantages of this amination are atom economy, solvent-free, chemoselectivity, short reaction time and high yields. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis and anti-viral activity of azolo-adamantanes against influenza A virus
  作者：Vladimir V. Zarubaev、Efim L. Golod、Pavel M. Anfimov、Anna A. Shtro、Victor V. Saraev、Alexey S. Gavrilov、Alexander V. Logvinov、Oleg I. Kiselev

  DOI：10.1016/j.bmc.2009.11.047

  日期：2010.1

  Chemotherapy and chemoprophylaxis of influenza is one of the most important directions of health protection activity. Due to the high rate of drug-resistant strains of influenza virus, there is a need for the search and further development of new potent antivirals against influenza with a broad spectrum of activity. In the present study, a set of di-, tri- and tetrazole derivatives of adamantane was efficiently prepared and their anti-influenza activities evaluated against rimantadine-resistant strain A/Puerto Rico/8/34. In general, derivatives of tetrazole possessed the highest virus-inhibiting activity. We demonstrated that several compounds of this set exhibited much higher activity than the currently used antiviral rimantadine, a compound of related structure. Moreover, we showed that these azolo-adamantanes were significantly less toxic. This study demonstrates that influenza viruses can be inhibited by adamantylazoles and thus have potential for developing antiviral agents with an alternate mechanism of action. (C) 2009 Elsevier Ltd. All rights reserved.