4-methyl-N-(phenyl(5-(phenyl(1H-pyrrol-2-yl)methyl)-1H-pyrrol-2-yl)methyl) benzene sulfonamide | 1137951-09-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-methyl-N-(phenyl(5-(phenyl(1H-pyrrol-2-yl)methyl)-1H-pyrrol-2-yl)methyl) benzene sulfonamide
• 英文别名: 4-methyl-N-(phenyl{5-[phenyl(1H-pyrrol-2-yl)methyl]-1H-pyrrol-2-yl}methyl)benzenesulfonamide；4-methyl-N-[phenyl-[5-[phenyl(1H-pyrrol-2-yl)methyl]-1H-pyrrol-2-yl]methyl]benzenesulfonamide
• CAS: 1137951-09-7
• 化学式: C₂₉H₂₇N₃O₂S
• 分子量: 481.618
• InChiKey: FKLITZBESLYFIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  86.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methyl-N-(phenyl(5-(phenyl(1H-pyrrol-2-yl)methyl)-1H-pyrrol-2-yl)methyl) benzene sulfonamide 在 copper(II) bis(trifluoromethanesulfonate) 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以42%的产率得到tetraphenylporphyrin
  参考文献：
  名称：

  Synthesis of meso-tetraphenyl porphyrins via condensation of dipyrromethanes with N-tosyl imines

  摘要：

  A new synthetic route for the synthesis of 5,10,15,20-tetraphenyl porphyrins has been developed based on the reaction of 5-substituted dipyrromethanes with N-tosyl imines in the presence of a metal triflate catalyst. meso-Substituted tetraphenyl porphyrins were synthesized in a two-step process. The first step of the method is the metal triflate-catalyzed condensation of 5-substituted dipyrromethanes with N-tosyl imines to form a porphyrinogen intermediate and the second step is the oxidation of the porphyrinogen to porphyrin. The method was applied to the synthesis of trans-A(2)B(2)-tetraarylporphyrins and the products were obtained with only a trace amount of one scrambling product. The synthesis of two important building blocks for porphyrin synthesis, mono and di-sulfonamide alkylated 5-substituted dipyrromethanes, was achieved by the addition of 5-substituted dipyrromethane to N-tosyl imine. The application of mono and di-sulfonamide alkylated 5-substituted dipyrromethanes in '2+2' porphyrin formation reactions is presented. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.01.009
• 作为产物：
  描述：

  N-tosyl-4-nitrobenzaldimine 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 4-methyl-N-(phenyl(5-(phenyl(1H-pyrrol-2-yl)methyl)-1H-pyrrol-2-yl)methyl) benzene sulfonamide
  参考文献：
  名称：

  三吡喃、四吡喃和Corroles的选择性合成

  摘要：

  开发了一种新的、催化的和通用的方法，用于通过二吡咯甲磺酰胺与吡咯的反应直接合成不对称的 AB 型三吡喃。关键结构二吡咯甲磺酰胺是通过向 Cu(OTf)2 活化的甲苯磺酰亚胺中添加内消旋取代的二吡咯甲烷来合成的。引入的方法能够通过调整加成反应的条件以高产率选择性地制备四吡喃。2,3-二氯-5,6-二氰基-1,4-苯醌氧化四吡喃仅提供相应的A3-和反式-A2B-corroles。

  DOI：

  10.1002/ejoc.201501062

文献信息

• Selective Synthesis of Tripyrranes, Tetrapyrranes, and Corroles
  作者：Gokcen Aydin、Baris Temelli、Canan Unaleroglu

  DOI：10.1002/ejoc.201501062

  日期：2015.12

  general methodology was developed for the direct synthesis of unsymmetrical AB-type tripyrranes by reaction of dipyrromethanesulfonamides with pyrrole. Key structure dipyrromethanesulfonamides were synthesized by the addition of meso-substituted dipyrromethanes to Cu(OTf)2-activated tosylimines. The introduced method enables selective preparation of tetrapyrranes in high yields by tuning the conditions of

  开发了一种新的、催化的和通用的方法，用于通过二吡咯甲磺酰胺与吡咯的反应直接合成不对称的 AB 型三吡喃。关键结构二吡咯甲磺酰胺是通过向 Cu(OTf)2 活化的甲苯磺酰亚胺中添加内消旋取代的二吡咯甲烷来合成的。引入的方法能够通过调整加成反应的条件以高产率选择性地制备四吡喃。2,3-二氯-5,6-二氰基-1,4-苯醌氧化四吡喃仅提供相应的A3-和反式-A2B-corroles。
• Synthesis of meso-tetraphenyl porphyrins via condensation of dipyrromethanes with N-tosyl imines
  作者：Baris Temelli、Canan Unaleroglu

  DOI：10.1016/j.tet.2009.01.009

  日期：2009.3

  A new synthetic route for the synthesis of 5,10,15,20-tetraphenyl porphyrins has been developed based on the reaction of 5-substituted dipyrromethanes with N-tosyl imines in the presence of a metal triflate catalyst. meso-Substituted tetraphenyl porphyrins were synthesized in a two-step process. The first step of the method is the metal triflate-catalyzed condensation of 5-substituted dipyrromethanes with N-tosyl imines to form a porphyrinogen intermediate and the second step is the oxidation of the porphyrinogen to porphyrin. The method was applied to the synthesis of trans-A(2)B(2)-tetraarylporphyrins and the products were obtained with only a trace amount of one scrambling product. The synthesis of two important building blocks for porphyrin synthesis, mono and di-sulfonamide alkylated 5-substituted dipyrromethanes, was achieved by the addition of 5-substituted dipyrromethane to N-tosyl imine. The application of mono and di-sulfonamide alkylated 5-substituted dipyrromethanes in '2+2' porphyrin formation reactions is presented. (C) 2009 Elsevier Ltd. All rights reserved.