1-ferrocenyl-3-(o-tolylamino)propan-1-one | 1342301-17-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-ferrocenyl-3-(o-tolylamino)propan-1-one
• 英文别名: cyclopenta-1,3-diene;1-cyclopenta-2,4-dien-1-yl-3-(2-methylanilino)propan-1-one;iron(2+)
• CAS: 1342301-17-0
• 化学式: C₂₀H₂₁FeNO
• 分子量: 347.24
• InChiKey: DLELFLJEQMUFGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-ferrocenyl-3-(o-tolylamino)propan-1-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of ferrocene-containing six-membered cyclic ureas via α-ferrocenyl carbocations

  摘要：

  开发了一种合成含有二茂铁的六元环脲的便利方法。

  DOI：

  10.1039/c5ra01383f
• 作为产物：
  描述：

  acryloylferrocene 、 邻甲苯胺 在 monmorillonite K-10 作用下， 以 neat (no solvent) 为溶剂， 生成 1-ferrocenyl-3-(o-tolylamino)propan-1-one
  参考文献：
  名称：

  抗菌剂3-（芳基氨基）-1-二茂铁基丙烷-1-酮：合成，光谱，电化学和结构表征

  摘要：

  通过将不同的芳基胺氮杂-迈克尔加成到丙烯酰基二茂铁中，已经以良好至优异的产率实现了十四种新的3-（芳基氨基）-1-二茂铁基丙烷-1-酮的合成。通过微波（MW）照射（500W / 5分钟）在没有溶剂的情况下反应物和蒙脱石K-10的混合物进行反应。对获得的化合物进行了光谱和电化学分析（循环伏安法），而其中的三个已进行了单晶X射线分析。在微量稀释测定中，尽管抑制程度有所不同，但所有化合物均显示对革兰氏阴性和阳性细菌具有广谱作用。观察到所有化合物在抑制重要的人类病原体金黄色葡萄球菌生长方面均具有显着活性。

  DOI：

  10.1016/j.jorganchem.2011.08.016

文献信息

• Synthesis, structural and electrochemical characterization of novel ferrocene-containing tetrahydropyrimidin-2(1H)-ones
  作者：Aleksandra Minić、Marko S. Pešić、Sladjana B. Novaković、Goran A. Bogdanović、Anka Todosijević、Danijela Ilić Komatina、Dragana Stevanović

  DOI：10.1016/j.jorganchem.2020.121422

  日期：2020.9

  1-aryl-4-ferrocenyltetrahidropyrimidin-2(1H)-ones were obtained in good to high yields (up to 93%). All products have been isolated in high purity >95%. In addition, we have provided a detailed structural characterization of the new compounds, which has been performed by IR and NMR spectroscopy. The single-crystal X-ray diffraction analysis was successfully performed on three representative examples, as well

  在此，我们报告了在冰川存在下，从相应的3-芳基氨基-1-二茂铁基丙烷-1-醇和氰酸钠（NaOCN）出发，易于合成含二茂铁的四氢嘧啶-2（1 H）-的简便方法。醋酸。该方案包括原位产生的1，3-羟基脲的分子内环化。已探究了针对11种含二茂铁的1,3-氨基醇的反应范围，并针对了1-芳基-4-二茂铁基四氢嘧啶2（1 H）-以高到高的产率（高达93％）获得。所有产品均以> 95％的高纯度分离。此外，我们提供了新化合物的详细结构特征，已通过IR和NMR光谱进行了表征。在三个代表性实例上成功进行了单晶X射线衍射分析以及元素分析。此外，已经对这三种结构的分子结构性质和分子间相互作用进行了比较和详细分析。用循环伏安法研究产物的电化学性能。这项研究揭示了准可逆的单电子氧化还原过程。
• Ferrocene-containing tetrahydropyrimidin-2(1H)-ones: Antioxidant and antimicrobial activity
  作者：Aleksandra Minić Jančić、Jelena S. Katanić Stanković、Nikola Srećković、Vladimir Mihailović、Danijela Ilić Komatina、Dragana Stevanović

  DOI：10.1016/j.jorganchem.2022.122335

  日期：2022.5

  antibacterial, and antifungal activity. The antioxidant activity of synthesized compounds was determined using two methods: ABTS radical cation and DPPH radical scavenging activities. The antimicrobial potential was evaluated in vitro employing three bacterial strains and three fungal strains. The synthesized compounds showed significantly lower antimicrobial activity compared with commercial antimicrobial

  一个包含六元环状脲环的二茂铁小型文库顺利合成，产率适中。已通过标准光谱方法以及元素分析确定了 > 95% 的纯度和所得化合物的结构表征。已使用循环伏安法提供了所制备化合物的电化学性质。筛选了17 种含二茂铁的四氢嘧啶-2(1 H )-酮的体外抗氧化、抗菌和抗真菌活性。使用两种方法测定合成化合物的抗氧化活性：ABTS 自由基阳离子和 DPPH 自由基清除活性。在体外评估抗菌潜力使用三种细菌菌株和三种真菌菌株。与商业抗菌化合物相比，合成的化合物显示出显着较低的抗菌活性，而合成的一些二茂铁衍生物具有较强的ABTS ·+清除活性。
• Synthesis of novel 4-ferrocenyl-1,2,3,4-tetrahydroquinolines and 4-ferrocenylquinolines via α-ferrocenyl carbenium ions as key intermediates
  作者：Aleksandra Minić、Dragana Stevanović、Mirjana Vukićević、Goran A. Bogdanović、Matthias D'hooghe、Niko S. Radulović、Rastko D. Vukićević

  DOI：10.1016/j.tet.2017.09.014

  日期：2017.11

  A series of novel 4-ferrocenyl-1,2,3,4-tetrahydroquinolines were synthesized in high-to-excellent yields (up to 99%) starting from the corresponding ferrocenoylethyl aryl amines. These Mannich bases were reduced (NaBH4) to the corresponding 3-(arylamino)-1-ferrocenylpropan-1-ols and submitted to an intramolecular cyclization prompted by acetic acid, proceeding via the corresponding α-ferrocenyl carbenium

  从相应的二茂铁酰基乙基芳基胺开始，以高至优异的产率（高达99％）合成了一系列新颖的4-二茂铁基-1,2,3,4-四氢喹啉。将这些曼尼希碱还原（NaBH 4）为相应的3-（芳基氨基）-1-二茂铁基丙烷-1-醇，并通过乙酸进行分子内环化，然后通过相应的α-二茂铁基碳鎓离子中间体进行。随后，将所获得的四氢喹啉通过2，3-二氯-5，6-二氰基-1，4-苯醌（DDQ）平滑地氧化（芳香化），以提供相应的4-二茂铁基喹啉（至多93％）。
• Synthesis, structural and electrochemical characterization of novel 1,3-ketoureas bearing a ferrocenyl group
  作者：Aleksandra Minić、Jovana P. Jovanović、Goran A. Bogdanović、Anka Pejović、Niko Radulović、Ivan Damljanović、Dragana Stevanović

  DOI：10.1016/j.poly.2017.12.018

  日期：2018.2

  ferrocene moiety were synthesized in good-to-excellent yields (up to 99%) via simple and efficient protocol. This solvent- and catalyst-free synthesis was achieved by additions of different ferrocene-containing Mannich bases – 3-(arylamino)-1-ferrocenylpropan-1-ones to phenyl isocyanate promoted only by ultrasound irradiations at ambient temperature. All synthesized 1-aryl-3-phenyl-1-(3-ferrocenyl-3-oxopropyl)ureas

  摘要通过简单有效的方法，以良好至优异的产率（高达99％）合成了22个带有二茂铁基团的新型1,3-酮基脲衍生物。这种无溶剂和无催化剂的合成是通过将不同的含二茂铁的曼尼希碱（3-（芳基氨基）-1-二茂铁基丙烷-1-酮）添加到异氰酸苯酯中来实现的，而异氰酸酯仅在环境温度下通过超声辐照才能促进。用标准光谱数据（1 H NMR，13 C NMR和IR）表征所有合成的1-芳基-3-苯基-1-（3-二茂铁基-3-氧丙基）脲，并通过循环伏安法研究其电化学行为。对三种代表性的含二茂铁的1,3-酮脲进行了详细的单晶X射线衍射分析，其中一个在两个不对称单元中被两个独立的分子结晶。
• Ultrasound-Assisted Synthesis of 3-(Arylamino)-1-ferrocenylpropan-1-ones
  作者：Anka Pejović、Dragana Stevanović、Ivan Damljanović、Mirjana Vukićević、Sladjana B. Novaković、Goran A. Bogdanović、Tatjana Mihajilov-Krstev、Niko Radulović、Rastko D. Vukićević

  DOI：10.1002/hlca.201200009

  日期：2012.8

  AbstractA successful aza‐Michael addition of arylamines to a conjugated enone, acryloylferrocene, has been achieved by ultrasonic irradiation of the mixture of these reactants and the catalyst, i.e., montmorillonite K‐10. This solvent‐free reaction, yielding ferrocene containing Mannich bases, 3‐(arylamino)‐1‐ferrocenylpropan‐1‐ones, considered as valuable precursors in organic synthesis, has been performed by using a simple ultrasonic cleaner. Among 17 synthesized β‐amino ketones, three were new ones, and these were fully characterized by spectroscopic means. X‐Ray crystallographic analysis of three of these crystalline products enabled the insight into the conformational details of these compounds. All compounds were evaluated for their antibacterial activities against six Gram‐positive and five Gram‐negative strains in a microdilution assay. The observed promising antibacterial activity (with a MIC value of 25 μg/ml (ca. 0.07 μmol/ml) as the best result for almost all tested compounds against Micrococcus flavus) seems not only to be compound but also bacterial species‐specific.