2-[1H-pyrrol-2-yl-(3,4,5-tris-decoxyphenyl)methyl]-1H-pyrrole | 1277116-19-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[1H-pyrrol-2-yl-(3,4,5-tris-decoxyphenyl)methyl]-1H-pyrrole
• CAS: 1277116-19-4
• 化学式: C₄₅H₇₄N₂O₃
• 分子量: 691.094
• InChiKey: MTHNSMXZHNNGMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.4
• 重原子数：
  50
• 可旋转键数：
  33
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  59.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-硝基苯基)炔丙醛 、 2-[1H-pyrrol-2-yl-(3,4,5-tris-decoxyphenyl)methyl]-1H-pyrrole 在 三氟化硼乙醚 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 反应 4.58h， 以12%的产率得到5,15-bis(3,4,5-trisdecyloxyphenyl)-10,20-bis(4-nitrophenylethynyl)porphyrin
  参考文献：
  名称：

  Synthesis of trans-A₂B₂-Porphyrins Bearing Phenylethynyl Substituents

  摘要：

  Efficient and convenient conditions for the preparation of trans-A(2)B(2)-porphyrins bearing two phenylethynyl moieties directly from phenylpropargyl aldehydes and dipyrromethanes of diversified lipophilicity and reactivity have been developed. This new procedure allows the preparation of a library of porphyrins of this architecture with a wide range of substituents. Thanks to the identification of the reagent solubility as one of the key factors influencing the yield of the porphyrinogens, we were able to improve yields to ca. 30%. The scope and limitations of two sets of conditions have been explored. The methodological advantage of this approach is its straightforward access to building blocks and the formation of the porphyrin core in the last step without the need for deprotection of the triple bond or bromination and consecutive coupling reaction, which often demands copper salts to proceed smoothly, especially with electron-deficient alkyne partners. Therefore, it prevents undesired copper porphyrin formation, as well as the need for utilizing expensive alkynes. A two-step method for the preparation of phenylpropargyl aldehydes has also been refined.

  DOI：

  10.1021/jo1025578
• 作为产物：
  描述：

  癸基溴 、 3,4,5-三羟基苯甲醛 在 potassium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 11.75h， 生成 2-[1H-pyrrol-2-yl-(3,4,5-tris-decoxyphenyl)methyl]-1H-pyrrole
  参考文献：
  名称：

  Synthesis of trans-A₂B₂-Porphyrins Bearing Phenylethynyl Substituents

  摘要：

  Efficient and convenient conditions for the preparation of trans-A(2)B(2)-porphyrins bearing two phenylethynyl moieties directly from phenylpropargyl aldehydes and dipyrromethanes of diversified lipophilicity and reactivity have been developed. This new procedure allows the preparation of a library of porphyrins of this architecture with a wide range of substituents. Thanks to the identification of the reagent solubility as one of the key factors influencing the yield of the porphyrinogens, we were able to improve yields to ca. 30%. The scope and limitations of two sets of conditions have been explored. The methodological advantage of this approach is its straightforward access to building blocks and the formation of the porphyrin core in the last step without the need for deprotection of the triple bond or bromination and consecutive coupling reaction, which often demands copper salts to proceed smoothly, especially with electron-deficient alkyne partners. Therefore, it prevents undesired copper porphyrin formation, as well as the need for utilizing expensive alkynes. A two-step method for the preparation of phenylpropargyl aldehydes has also been refined.

  DOI：

  10.1021/jo1025578

文献信息

• Synthesis of <i>trans</i>-A₂B₂-Porphyrins Bearing Phenylethynyl Substituents
  作者：Agnieszka Nowak-Król、Beata Koszarna、Su Yeon Yoo、Jan Chromiński、Marek K. Wȩcławski、Chang-Hee Lee、Daniel T. Gryko

  DOI：10.1021/jo1025578

  日期：2011.4.15

  Efficient and convenient conditions for the preparation of trans-A(2)B(2)-porphyrins bearing two phenylethynyl moieties directly from phenylpropargyl aldehydes and dipyrromethanes of diversified lipophilicity and reactivity have been developed. This new procedure allows the preparation of a library of porphyrins of this architecture with a wide range of substituents. Thanks to the identification of the reagent solubility as one of the key factors influencing the yield of the porphyrinogens, we were able to improve yields to ca. 30%. The scope and limitations of two sets of conditions have been explored. The methodological advantage of this approach is its straightforward access to building blocks and the formation of the porphyrin core in the last step without the need for deprotection of the triple bond or bromination and consecutive coupling reaction, which often demands copper salts to proceed smoothly, especially with electron-deficient alkyne partners. Therefore, it prevents undesired copper porphyrin formation, as well as the need for utilizing expensive alkynes. A two-step method for the preparation of phenylpropargyl aldehydes has also been refined.