4-bromophenyl 1-(3-imidazolylpropyl)-4-(2-naphthyl)imidazol-5-yl ketone | 263389-21-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-bromophenyl 1-(3-imidazolylpropyl)-4-(2-naphthyl)imidazol-5-yl ketone
• 英文别名: (4-Bromophenyl)[1-[3-(1H-imidazol-1-yl)propyl]-4-(2-naphthalenyl)-1H-imidazol-5-yl]methanone；(4-bromophenyl)-[3-(3-imidazol-1-ylpropyl)-5-naphthalen-2-ylimidazol-4-yl]methanone
• CAS: 263389-21-5
• 化学式: C₂₆H₂₁BrN₄O
• 分子量: 485.383
• InChiKey: BOXLCBOESUQUOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  52.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  二乙二醛对溴苯 在 哌嗪 、 三乙胺 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 25.0h， 生成 4-bromophenyl 1-(3-imidazolylpropyl)-4-(2-naphthyl)imidazol-5-yl ketone
  参考文献：
  名称：

  An Investigation of Imidazole and Oxazole Syntheses Using Aryl-Substituted TosMIC Reagents¹

  摘要：

  This article describes efficient and mild protocols for preparing polysubstituted imidazoles in a single pot fi om aryl-substituted tosylmethyl isocyanide (TosMIC) reagents and imines generated in situ. Traditional imine-forming reactions employing virtually any aldehyde and amine followed by addition of the TosMIC reagent delivers 1,4,5-trisubstituted imidazoles with predictable regiochemistry. Employing chiral amines and aldehydes, particularly those derived from or-amino acids, affords imidazoles with asymmetric centers appended to N-1 or C-5 with excellent retention of chiral purity. 1,4-Disubstituted imidazoles are also readily prepared by a simple variant of the above procedure. Selecting glyoxylic acid as the aldehyde component of this procedure leads to intermediates such as 48, which readily undergo decarboxylation and elimination oft;he tosyl moiety to deliver 1,4-disubstituted imidazoles in high yields. Alternatively, using NH4OH as the amine component in conjunction with a variety of aldehydes delivers 4,5-disubstituted imidazoles in moderate to good yields in a single pot while avoiding the need for protecting groups. Finally, the facile preparation of mono- and disubstituted oxazoles from these TosMIC reagents and aldehydes is described.

  DOI：

  10.1021/jo991782l

文献信息

• An Investigation of Imidazole and Oxazole Syntheses Using Aryl-Substituted TosMIC Reagents¹
  作者：Joseph Sisko、Andrew J. Kassick、Mark Mellinger、John J. Filan、Andrew Allen、Mark A. Olsen

  DOI：10.1021/jo991782l

  日期：2000.3.1

  This article describes efficient and mild protocols for preparing polysubstituted imidazoles in a single pot fi om aryl-substituted tosylmethyl isocyanide (TosMIC) reagents and imines generated in situ. Traditional imine-forming reactions employing virtually any aldehyde and amine followed by addition of the TosMIC reagent delivers 1,4,5-trisubstituted imidazoles with predictable regiochemistry. Employing chiral amines and aldehydes, particularly those derived from or-amino acids, affords imidazoles with asymmetric centers appended to N-1 or C-5 with excellent retention of chiral purity. 1,4-Disubstituted imidazoles are also readily prepared by a simple variant of the above procedure. Selecting glyoxylic acid as the aldehyde component of this procedure leads to intermediates such as 48, which readily undergo decarboxylation and elimination oft;he tosyl moiety to deliver 1,4-disubstituted imidazoles in high yields. Alternatively, using NH4OH as the amine component in conjunction with a variety of aldehydes delivers 4,5-disubstituted imidazoles in moderate to good yields in a single pot while avoiding the need for protecting groups. Finally, the facile preparation of mono- and disubstituted oxazoles from these TosMIC reagents and aldehydes is described.