2-(4-methoxyphenyl)-5-methyl-3H-imidazole-4-carboxylic acid (1-hydroxymethyl-2-phenylethyl)amide | 618904-95-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-methoxyphenyl)-5-methyl-3H-imidazole-4-carboxylic acid (1-hydroxymethyl-2-phenylethyl)amide
• 英文别名: N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]-2-(4-methoxyphenyl)-5-methyl-1H-imidazole-4-carboxamide
• CAS: 618904-95-3
• 化学式: C₂₁H₂₃N₃O₃
• 分子量: 365.432
• InChiKey: PGDNBSLNEKJGAS-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  87.2
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-methoxyphenyl)-5-methyl-3H-imidazole-4-carboxylic acid (1-hydroxymethyl-2-phenylethyl)amide 在 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 7-allyl-6-benzyl-3-(4-methoxyphenyl)-1-methyl-6,7-dihydro-5H-imidazo[1,5-a]pyrazin-8-one
  参考文献：
  名称：

  Novel Synthetic Approach to 6,7-Dihydro-5H-imidazo[1,5-a]-pyrazin-8-ones

  摘要：

  [GRAPHICS]A novel route to highly substituted chiral 6,7-dihydro-5H-imidazo[1,5-a]pyrazine-8-ones starting from Meldrum's acid is disclosed. The key features of the methodology are the incorporation of amino esters as a chiral pool and facile mild intramolecular cyclization to form the pyrazine ring. Incorporation of various substituents at different stages of the synthesis from various building block sets makes this methodology readily amenable to parallel synthesis.

  DOI：

  10.1021/ol035455i
• 作为产物：
  描述：

  2-(3-oxo-butyrylamino)-3-phenylpropionic acid methyl ester 在 lithium aluminium tetrahydride 、 三乙胺 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 2.75h， 生成 2-(4-methoxyphenyl)-5-methyl-3H-imidazole-4-carboxylic acid (1-hydroxymethyl-2-phenylethyl)amide
  参考文献：
  名称：

  Novel Synthetic Approach to 6,7-Dihydro-5H-imidazo[1,5-a]-pyrazin-8-ones

  摘要：

  [GRAPHICS]A novel route to highly substituted chiral 6,7-dihydro-5H-imidazo[1,5-a]pyrazine-8-ones starting from Meldrum's acid is disclosed. The key features of the methodology are the incorporation of amino esters as a chiral pool and facile mild intramolecular cyclization to form the pyrazine ring. Incorporation of various substituents at different stages of the synthesis from various building block sets makes this methodology readily amenable to parallel synthesis.

  DOI：

  10.1021/ol035455i