1-bromo-15-(4-tert-butylphenyl)-19-(4-ethylbenzoyl)-10-pentyl-5-phenylbilane | 1051918-21-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-bromo-15-(4-tert-butylphenyl)-19-(4-ethylbenzoyl)-10-pentyl-5-phenylbilane
• CAS: 1051918-21-8
• 化学式: C₄₉H₅₃BrN₄O
• 分子量: 793.89
• InChiKey: BPYHELPWZFZFLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.92
• 重原子数：
  55.0
• 可旋转键数：
  15.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  80.23
• 氢给体数：
  4.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-bromo-15-(4-tert-butylphenyl)-19-(4-ethylbenzoyl)-10-pentyl-5-phenylbilane 在 air 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 magnesium bromide 作用下， 以 甲苯 为溶剂， 以46%的产率得到20-(4-tert-butylphenyl)-5-(4-ethylphenyl)-15-pentyl-10-phenylporphinatomagnesium(II)
  参考文献：
  名称：

  Investigation of the Scope of a New Route to ABCD-Bilanes and ABCD-Porphyrins

  摘要：

  A new route to bilanes and porphyrins bearing four distinct meso substituents has been studied to elucidate the scope and gain entry to previously inaccessible compounds. The route entails (i) synthesis of a 1-bromo-19-acylbilane by acid-catalyzed condensation of a 1-acyldipyrromethane and a 9-bromodipyrromethane-1-carbinol and (ii) intramolecular cyclization of the 1-bromo-19-acylbilane in the presence of a metal salt (MgBr2, 3 mol equiv) and a non-nucleophilic base (DBU, 10 mol equiv) in a noncoordinating solvent (toluene) at 115 degrees C exposed to air to afford the corresponding magnesium(II) porphyrin. In this study, two sets of bilanes were initially prepared to explore substituent effects. In the first set, all bilanes vary only in the nature of the substituent at the 10-position. In the second set, all bilanes vary only in the nature of the substituent attached to the acyl unit (the 20-position). The substituents examined at the 10- and 20-positions include alkyl, aryl (electron-rich, electron-deficient, hindered), heteroaryl, ester, or no substituent (-H). The bilanes were obtained in 35-87% yield, and the target porphyrins in up to 60% yield. Further study of the scope focused on bilanes and porphyrins bearing three heterocyclic substituents (o-, m-, p-pyridyl) or four alkyl groups (ethyl, propyl, butyl, pentyl), in which case microwave irradiation was used for the porphyrin-forming step. Altogether, 17 bilanes and 19 porphyrins were prepared and characterized. In summary, the new route provides access to meso-substituted bilanes and porphyrins for which access is limited via other methods.

  DOI：

  10.1021/jo8010396
• 作为产物：
  描述：

  5-(4-tert-butylphenyl)-1-(4-ethylbenzoyl)dipyrromethane 、 在 ytterbium(III) triflate 作用下， 以 甲醇 、 乙醚 、 乙腈 为溶剂， 以0.673 g的产率得到1-bromo-15-(4-tert-butylphenyl)-19-(4-ethylbenzoyl)-10-pentyl-5-phenylbilane
  参考文献：
  名称：

  Investigation of the Scope of a New Route to ABCD-Bilanes and ABCD-Porphyrins

  摘要：

  A new route to bilanes and porphyrins bearing four distinct meso substituents has been studied to elucidate the scope and gain entry to previously inaccessible compounds. The route entails (i) synthesis of a 1-bromo-19-acylbilane by acid-catalyzed condensation of a 1-acyldipyrromethane and a 9-bromodipyrromethane-1-carbinol and (ii) intramolecular cyclization of the 1-bromo-19-acylbilane in the presence of a metal salt (MgBr2, 3 mol equiv) and a non-nucleophilic base (DBU, 10 mol equiv) in a noncoordinating solvent (toluene) at 115 degrees C exposed to air to afford the corresponding magnesium(II) porphyrin. In this study, two sets of bilanes were initially prepared to explore substituent effects. In the first set, all bilanes vary only in the nature of the substituent at the 10-position. In the second set, all bilanes vary only in the nature of the substituent attached to the acyl unit (the 20-position). The substituents examined at the 10- and 20-positions include alkyl, aryl (electron-rich, electron-deficient, hindered), heteroaryl, ester, or no substituent (-H). The bilanes were obtained in 35-87% yield, and the target porphyrins in up to 60% yield. Further study of the scope focused on bilanes and porphyrins bearing three heterocyclic substituents (o-, m-, p-pyridyl) or four alkyl groups (ethyl, propyl, butyl, pentyl), in which case microwave irradiation was used for the porphyrin-forming step. Altogether, 17 bilanes and 19 porphyrins were prepared and characterized. In summary, the new route provides access to meso-substituted bilanes and porphyrins for which access is limited via other methods.

  DOI：

  10.1021/jo8010396