tri-(1-methylpyrrol-2-yl)methane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: tri-(1-methylpyrrol-2-yl)methane
• 英文别名: tris(N-methyl-2-pyrrolyl)methane；2-[Bis(1-methylpyrrol-2-yl)methyl]-1-methylpyrrole
• 化学式: C₁₆H₁₉N₃
• 分子量: 253.347
• InChiKey: PZCQMJJJICGZSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  14.8
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  N-甲基吡咯 、 原甲酸三乙酯 在 bismuth(lll) trifluoromethanesulfonate 作用下， 以 neat liquid 为溶剂， 反应 1.0h， 以43%的产率得到tri-(1-methylpyrrol-2-yl)methane
  参考文献：
  名称：

  Bi（OTf）3催化芳烃/杂芳烃与原甲酸三烷基酯的Friedel-Crafts反应一锅法合成三芳基和三杂芳基甲烷

  摘要：

  已经开发了一种方便，实用，高效的一锅法，该方法通过在室温下用Bi（OTf）3催化三烷基原甲酸酯的Friedel-Crafts烷基化与多种芳烃/杂芳烃结合来合成三芳基和三杂芳基甲烷衍生物无溶剂条件下和大气中的最高温度。该方法提供了操作简便性，高原子经济性和对环境有益的程序。此外，选择的化合物3k在抑制一氧化氮方面显示出有希望的抗炎活性，并且对巨噬细胞没有显着的细胞毒性作用。

  DOI：

  10.1016/j.tet.2018.05.079

文献信息

• Reactions between pyrrole and orthoesters: preparation of tri-(pyrrol-2-yl)alkanes
  作者：Colin B Reese、Hongbin Yan

  DOI：10.1016/s0040-4039(01)01031-0

  日期：2001.8

  Reactions between triethyl orthoformate, trimethyl orthoacetate and triethyl orthopropionate with pyrrole and chloroacetic acid lead to moderate yields of the corresponding tri-(pyrrol-2-yl)alkanes 5a, 5b and 5c, respectively. Under the same conditions, trimethyl orthobenzoate reacts with pyrrole and dichloroacetic acid to give the dipyrrin 7 in a relatively good yield.

  原甲酸三乙酯，原乙酸三甲酯和原丙酸三乙酯与吡咯和氯乙酸的反应分别导致相应的三（吡咯-2-基）烷烃5a，5b和5c的中等产率。在相同条件下，原苯甲酸三甲酯与吡咯和二氯乙酸反应，以相对较高的产率得到双吡啶7。
• Unique versatility of Amberlyst 15. An acid and solvent-free paradigm towards synthesis of bis(heterocyclyl)methane derivatives
  作者：Kamaljit Singh、Shivali Sharma、Amit Sharma

  DOI：10.1016/j.molcata.2011.07.007

  日期：2011.8

  Bis(heterocyclyl)methanes, key intermediates for a variety of chemical, biochemical and material science relevant targets, have been obtained in a synthetically useful manner using Amberlyst 15 ion-exchange resin. This method promises versatility, cost-effectiveness, and efficiency. (C) 2011 Elsevier B.V. All rights reserved.
• Pentoses and Hexoses as Sources of New Melanoidin-like Maillard Polymers
  作者：Roland Tressl、Georg T. Wondrak、Leif-A. Garbe、Ralph-Peter Krüger、Dieter Rewicki

  DOI：10.1021/jf970973r

  日期：1998.5.1

  N-Substituted pyrroles (1), 2-furaldehyde (2), and N-substituted 2-formylpyrroles (3), formed in pentose (hexose) Maillard systems, were identified as components of extraordinary polycondensation activity. The polycondensation was studied in model experiments with N-methylpyrrole (1a)/N-methyl-2-formylpyrrole (3a), N-(2-methoxycarbonylethyl)pyrrole (1b)/N-(2-methoxycarbonylethyl)-2-formylpyrrole (3b), N-methyl-2-formylpyrrole (3a), N-methylpyrrole (1a)/2-furaldehyde (2), and N-(2-methoxycarbonylethyl)pyrrole (1b)/2-furaldehyde (2), respectively. MALDI-TOF-MS spectra indicated regular oligomers of up to 15-30 methine-bridged N-methyl(or N-2-methoxycarbonylethyl)-pyrroles. With participation of aldehyde 2, furan rings instead of pyrrole rings were incorporated. The oligomers 5-11 were isolated and identified by MS and NMR techniques. A complementary experiment with N-methyl-2-[C-13]formylpyrrole ([(CHO)-C-13]-3a)/N-methylpyrrole (1a) was performed. The relevance of the new (type II) melanoidin-like oligomers/polymers in Maillard reactions is discussed and, in conclusion, a corresponding structure for native melanoidins is proposed. The oligomers 5, 6, 8, and 9 were tested for antioxidative activity in an iron(III) thiocyanate assay.
• One-pot solvent-free synthesis of triaryl- and triheteroarylmethanes by Bi(OTf)3-catalyzed Friedel-Crafts reaction of arenes/heteroarenes with trialkyl orthoformates
  作者：Surisa Tuengpanya、Chayamon Chantana、Uthaiwan Sirion、Wipada Siritanyong、Klaokwan Srisook、Jaray Jaratjaroonphong

  DOI：10.1016/j.tet.2018.05.079

  日期：2018.8

  A convenient, practical and highly efficient one-pot method has been developed for the synthesis of triaryl- and triheteroarylmethane derivatives by Bi(OTf)3-catalyzed Friedel-Crafts alkylation of trialkyl orthoformates in combination with a wide variety of arenes/heteroarenes at room temperature under solvent-free conditions and in an air atmosphere. The methodology offers an operational simplicity

  已经开发了一种方便，实用，高效的一锅法，该方法通过在室温下用Bi（OTf）3催化三烷基原甲酸酯的Friedel-Crafts烷基化与多种芳烃/杂芳烃结合来合成三芳基和三杂芳基甲烷衍生物无溶剂条件下和大气中的最高温度。该方法提供了操作简便性，高原子经济性和对环境有益的程序。此外，选择的化合物3k在抑制一氧化氮方面显示出有希望的抗炎活性，并且对巨噬细胞没有显着的细胞毒性作用。