1-ferrocenylmethyl-1H-1,2,4-triazole | 713108-31-7

• 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-ferrocenylmethyl-1H-1,2,4-triazole
• 英文别名: ferrocene methyltriazole；ferrocenylmethyl-1,2,4-triazole；1-N-(ferrocenylmethyl)-1,2,4-triazole；1-ferrocenylmethyl-1,2,4-triazole；1-(ferrocenylmethyltrimethyl)triazole
• CAS: 713108-31-7
• 化学式: C₁₃H₁₃FeN₃
• 分子量: 267.113
• InChiKey: MCBBMMOJIYUQAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  癸基溴 、 1-ferrocenylmethyl-1H-1,2,4-triazole 以 乙腈 为溶剂， 以78%的产率得到1-(ferrocenylmethyl)-3-decyl-1,2,4-triazolium bromide
  参考文献：
  名称：

  Anticancer activity and molecular docking studies of ferrocene tethered ionic liquids

  摘要：

  A novel series of ferrocene tethered ionic liquids (ILs) has been synthesized by quaternization of 1-N-(ferrocenylmethyl)benzimidazole, 1-N-(ferrocenylmethyl)imidazole and 1-N-(ferrocenylmethyl)-1,2,4-triazole with long chain alkyl bromides. The synthesized ILs were screened for their anticancer activity against human breast cancer cell line MCF-7. ILs 2a-d and 4b displayed significant anticancer activity (GI(50) 0.016-0.064 mu M). IL 2d was found to be the most active with GI(50) value of 0.016 mu M which was even less than the standard drug doxorubicin (GI(50) = 0.018 mu M). AII ILs exhibit moderate to good selectivity against breast cancer cells MCF-7 over normal Vero cells. The ADME prediction studies revealed that all the ILs exhibit good pharmacological parameters. The molecular docking studies ascertained mode of action of the ILs via inhibition of lysosomal peptidase cathepsin B. (C) 2019 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molliq.2019.111182
• 作为产物：
  描述：

  1H-1,2,4-三唑 、 N,N,N-(ferrocenylmethyl)trimethylammonium iodide 以 not given 为溶剂， 以65%的产率得到1-ferrocenylmethyl-1H-1,2,4-triazole
  参考文献：
  名称：

  The First (Ferrocenylmethyl)imidazolium and (Ferrocenylmethyl)triazolium Room Temperature Ionic Liquids

  摘要：

  N-(Ferrocenylmethyl)imidazole (3a), 1-(ferrocenylmethyl)-1,2,4-triazole (3b), 1,1'-bis[(1H-imidazol-1-yl)methyl]ferrocene (8a), 1,1'-bis [(1H-(2-methyl)imidazol-1-yl)methyl]ferrocene (8b), and 1,1'-bis[(1H-1,2,4-triazol-1-yl)methyl]ferrocene (8c) were synthesized in moderate yields. These compounds were quaternized with methyl iodide to form 1-(ferrocenylmethyl)-3-methylimidazolium iodide (4a), 1-(ferrocenylmethyl)-4-methyl-1,2,4-triazolium iodide (4b), 1,1'-bis{[1-(2,3-dimethyl)imidazolium]methyl}ferrocene diiodide (9b), and 1,1'-bis{[1-(4-methyl)-1,2,4-triazolium]methyl}ferrocene diiodide (9c), respectively, in excellent yields. Compounds 4a, 4b, 9b, and 9c were metathesized with bis(trifluoromethanesulfonyl)amide to give high yields of 5a, 5b, 10b, and 10c. With potassium hexafluorophosphate, 9b forms 10d. Salts 5a, 5b, and 10c are the first room-temperature ionic liquids with cations containing an organometallic moiety that exhibit T-g values well below room temperature, i.e., -32, -16, and -11 degreesC. The compounds were characterized by H-1, F-19, and C-13 NMR, MS, and elemental analyses. T-g values and melting points were determined by DSC. T-d values (5% weight loss temperature) were recorded by TGA. X-ray single-crystal structures show that 9c and 10d crystallize in the triclinic space group P (1) over bar.

  DOI：

  10.1021/ic049961v

文献信息

• Unexpected acid-catalyzed ferrocenylmethylation of diverse nucleophiles with vinyloxymethylferrocene
  作者：Ludmila A. Oparina、Alexander V. Artem'ev、Oksana V. Vysotskaya、Olga A. Tarasova、Vladimir A. Shagun、Irina Yu. Bagryanskaya、Boris A. Trofimov

  DOI：10.1016/j.tet.2016.06.012

  日期：2016.7

  A new efficient approach for the ferrocenylmethylation of various alcohols, OH-, SH- and SeH-acids (carboxylic, thio- and selenophosphinic) as well as 1H-triazoles is elaborated based on the acid-catalyzed reaction with available vinyloxymethylferrocene. The reaction readily occurs under mild conditions to afford product of O-, N-, S- and Se-ferrocenylmethylation of the corresponding nucleophiles in

  基于与可用的乙烯基氧甲基二茂铁的酸催化反应，阐述了一种新的有效方法，用于各种醇，OH-，SH-和SeH-酸（羧酸，硫代和硒代膦酸）以及1 H-三唑的二茂铁基甲基化。该反应在温和条件下容易发生，以良好至高产率获得相应亲核试剂的O-，N-，S-和Se-二茂铁基甲基化产物。
• Ionic Ferrocenyl Coordination Compounds Derived from Imidazole and 1,2,4-Triazole Ligands and Their Catalytic Effects During Combustion
  作者：Na Zhang、Guofang Zhang、Jizhen Li、Weiqiang Zhang、Ziwei Gao

  DOI：10.1002/zaac.201700429

  日期：2018.4.3

  Alkylferrocene‐based burning‐rate catalysts (BRCs) show conspicuous migration tendency and volatility during prolonged storage and fabrication process of a composite solid propellant. To enhance anti‐migration ability of the BRCs, forty novel ionic coordination compounds, [M(L)4(H2O)2]mXn (M = Mn2+, Co2+, Cu2+, Ni2+, Zn2+, Fe2+, Pb2+, Cr3+, Bi3+, or Cd2+; L = ferrocenylmethyl imidazole or ferrocenylmethyl‐1

  基于烷基二茂铁的燃烧速率催化剂（BRC）在复合固体推进剂的长期储存和制造过程中表现出明显的迁移趋势和挥发性。为了增强BRC的抗迁移能力，使用了40种新型离子配位化合物[ M（L）4（H 2 O）2 ] m X n（M = Mn 2 +，Co 2 +，Cu 2 +，Ni 2+，Zn 2 +，Fe 2 +，Pb 2 +，Cr 3+，Bi 3+或Cd 2+; L =二茂铁基甲基咪唑或二茂铁基甲基1,2,4-三唑; X=苦味酸或三硝基间苯二酸酯），并通过FT-IR，UV / Vis和元素分析对其进行了表征。此外，通过单晶X射线衍射确认了6种化合物的晶体结构。TG分析表明，新化合物显示出高的热稳定性。循环伏安法研究表明它们是不可逆的氧化还原系统。它们在高氯酸铵（AP），1,3,5-三硝基-1,3,5-三氮杂环己烷（RDX）和1,2,5,7-四硝基-1,3,5的热降解中的催化活性用DSC技术检测了7,
• 二茂铁离子型高氮金属配合物及其制备方法
  申请人：陕西师范大学

  公开号：CN106831888B

  公开（公告）日：2019-04-12

  本发明公开了一种二茂铁离子型高氮金属配合物及其制备方法，该配合物的结构式为式中M代表Mn2+、Co2+、Cu2+、Ni2+、Pb2+中的任意一种，X代表C或N，L代表苦味酸根或三硝基间苯二酚二价负离子，其中L代表苦味酸根时，n＝2，L代表三硝基间苯二酚二价负离子时，n＝1。本发明配合物引入的金属离子提高了其抗迁移性并能够降低其挥发性，由于引入的配体和多硝基酚负离子自身具有较高的生成热和燃烧热，提高了其对高氯酸铵热分解过程的燃烧催化性能，本发明配合物制备方法简单。
• ——
  作者：V. V. Gumenyuk、Z. A. Starikova、Yu. S. Nekrasov、V. N. Babin

  DOI：10.1023/a:1021360704054

  日期：——

  Ferrocenylmethylation and alpha-ferrocenylethylation of indazole were carried out for the first time. Both reactions afforded two isomers, which were characterized by physical and physicochemical methods, among them by X-ray diffraction analysis. 1-(alpha-Ferrocenylethyl)indazole is thermally more stable than the 2-substituted isomer. Both isomers serve as ferrocenylalkylating agents with respect to s-triazole.