1-甲基-2-[(1-甲基吡咯-2-基)-苯基甲基]吡咯 | 852928-16-6

• 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-甲基-2-[(1-甲基吡咯-2-基)-苯基甲基]吡咯
• 英文名称: N-methyl-2-[1-phenyl-1-(2'-N-methylpyrrolyl)-methyl]-pyrrole
• 英文别名: bis(1-methyl-1H-pyrrol-2-yl)(phenyl)methane；5-(phenyl)-N,N'-dimethyldipyrromethane；1H-Pyrrole, 2,2'-(phenylmethylene)bis[1-methyl-；1-methyl-2-[(1-methylpyrrol-2-yl)-phenylmethyl]pyrrole
• CAS: 852928-16-6
• 化学式: C₁₇H₁₈N₂
• 分子量: 250.343
• InChiKey: OTEZHQFYZAZRKU-UHFFFAOYSA-N

物化性质

• 熔点：
  84 °C
• 沸点：
  379.1±32.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  9.9
• 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 、 N-tosylbenzaldimine 在 copper(II) bis(trifluoromethanesulfonate) 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 二氯甲烷 为溶剂， 以42%的产率得到1-甲基-2-[(1-甲基吡咯-2-基)-苯基甲基]吡咯
  参考文献：
  名称：

  Understanding the Behavior of N-Tosyl and N-2-Pyridylsulfonyl Imines in Cu^II-Catalyzed Aza-Friedel−Crafts Reactions

  摘要：

  [GRAPHICS]The different behavior of N-tosyl imines and N-(2-pyridyl)sulfonyl imines in Cu-II-catalyzed AFCR is described. DFT theoretical calculations on the mode of coordination of the copper atom to both types of substrates allow understanding this different reactivity.

  DOI：

  10.1021/jo800986g

文献信息

• 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.
• Organocatalytic synthesis of dipyrromethanes by the addition of N-methylpyrrole to aldehydes
  作者：Cinzia Biaggi、Maurizio Benaglia、Laura Raimondi、Franco Cozzi

  DOI：10.1016/j.tet.2006.09.104

  日期：2006.12

  The reaction of aldehydes with N-methylpyrrole carried out in the presence of catalytic pyrrolidinium tetrafluoroborate at room temperature affords the corresponding dipyrromethanes and minor amounts of tripyrranes. This new, mild, and convenient process represents the first organocatalytic synthesis of dipyrromethanes. The products are obtained in chemical yields similar to those obtained with existing methods, which, however, require either a much larger excess of heterocycle (when aldehydes are employed as starting materials), or more drastic reaction conditions (when aldehyde equivalents are used as starting materials) than those employed here. A mechanism is proposed to explain the course of this reaction. (c) 2006 Elsevier Ltd. All rights reserved.
• Efficient and versatile single pot approach to dipyrromethanes and bis(heterocyclyl)methanes
  作者：Kamaljit Singh、Sonia Behal、Maninder Singh Hundal

  DOI：10.1016/j.tet.2005.04.029

  日期：2005.7

  An efficient single pot route is presented involving the use of 0, N-perhydro 1,3-heterocycles as carbonyl equivalents for the synthesis of 5-substituted dipyrromethanes, 5,10-disubstituted tripyrranes and bis(heterocyclyl)methanes. (c) 2005 Elsevier Ltd. All rights reserved.
• Understanding the Behavior of <i>N</i>-Tosyl and <i>N</i>-2-Pyridylsulfonyl Imines in Cu^II-Catalyzed Aza-Friedel−Crafts Reactions
  作者：Inés Alonso、Jorge Esquivias、Ramón Gómez-Arrayás、Juan C. Carretero

  DOI：10.1021/jo800986g

  日期：2008.8.1

  [GRAPHICS]The different behavior of N-tosyl imines and N-(2-pyridyl)sulfonyl imines in Cu-II-catalyzed AFCR is described. DFT theoretical calculations on the mode of coordination of the copper atom to both types of substrates allow understanding this different reactivity.