2,5-bis[phenyl-[5-[phenyl(1H-pyrrol-2-yl)methyl]-1H-pyrrol-2-yl]methyl]-1H-pyrrole | 359017-37-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: 2,5-bis[phenyl-[5-[phenyl(1H-pyrrol-2-yl)methyl]-1H-pyrrol-2-yl]methyl]-1H-pyrrole
• CAS: 359017-37-1
• 化学式: C₄₈H₄₁N₅
• 分子量: 687.887
• InChiKey: UWBRSDQPENWELV-UHFFFAOYSA-N

物化性质

• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  53
• 可旋转键数：
  12
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  79
• 氢给体数：
  5
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,5-bis[phenyl-[5-[phenyl(1H-pyrrol-2-yl)methyl]-1H-pyrrol-2-yl]methyl]-1H-pyrrole 在 氯化铵 、 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 1.0h， 生成 tetraphenylporphyrin
  参考文献：
  名称：

  Unusual phlorins from the oxidative coupling of pentapyrromethanes: their facile conversion to meso-substituted porphyrins

  摘要：

  Direct, oxidant-mediated intramolecular coupling of pentapyrromethanes afforded 5-aryl-5-(2 ' -pyrryl)-10,15,20-triaryl-porphyrin (phlorins) as single products. The outcome of the reaction is comparable with the oxidative coupling of tetra-pyrromethanes. Treatment of obtained phlorins with trifluoroacetic acid resulted in exclusive elimination of the peripheral pyrrole affording mwso-tetraarylporphyrins quantitatively. The rate of pyrrole elimination depends on the acid concentration. The selective binding with fluoride anion was also observed with a large association constant. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)00783-3
• 作为产物：
  描述：

  吡咯 、 苯甲醛 在 四氢吡咯 、 tetrafluoroboric acid 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以30%的产率得到5,10-diphenyltripyrrane
  参考文献：
  名称：

  Organocatalytic synthesis of dipyrromethanes by the addition of N-methylpyrrole to aldehydes

  摘要：

  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.

  DOI：

  10.1016/j.tet.2006.09.104

文献信息

• 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.
• Unusual phlorins from the oxidative coupling of pentapyrromethanes: their facile conversion to meso-substituted porphyrins
  作者：Jae-Won Ka、Chang-Hee Lee

  DOI：10.1016/s0040-4039(01)00783-3

  日期：2001.7

  Direct, oxidant-mediated intramolecular coupling of pentapyrromethanes afforded 5-aryl-5-(2 ' -pyrryl)-10,15,20-triaryl-porphyrin (phlorins) as single products. The outcome of the reaction is comparable with the oxidative coupling of tetra-pyrromethanes. Treatment of obtained phlorins with trifluoroacetic acid resulted in exclusive elimination of the peripheral pyrrole affording mwso-tetraarylporphyrins quantitatively. The rate of pyrrole elimination depends on the acid concentration. The selective binding with fluoride anion was also observed with a large association constant. (C) 2001 Published by Elsevier Science Ltd.