(3S,8aR)-3-isopropyl-1-(4-methylphenyl)hexahydroimidazo[1,2-a]pyridin-2(3H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (3S,8aR)-3-isopropyl-1-(4-methylphenyl)hexahydroimidazo[1,2-a]pyridin-2(3H)-one
• 英文别名: (3S,8aR)-1-(4-methylphenyl)-3-propan-2-yl-3,5,6,7,8,8a-hexahydroimidazo[1,2-a]pyridin-2-one
• 化学式: C₁₇H₂₄N₂O
• 分子量: 272.39
• InChiKey: ZLNLJKWGOIDJBJ-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  tert-butyl N-[(1S)-2-methyl-1-(4-toluidinocarbonyl)propyl]carbamate 在 盐酸 、 T406石油添加剂 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 24.0h， 生成 (3S,8aR)-3-isopropyl-1-(4-methylphenyl)hexahydroimidazo[1,2-a]pyridin-2(3H)-one
  参考文献：
  名称：

  Syntheses of Optically Active Tetrahydro-1H-pyrrolo[1,2-a]imidazol-2-ones and Hexahydroimidazo[1,2-a]pyridin-2(3H)-ones

  摘要：

  The reactions of (2S)-2-amino-2-substituted-N-(4-nitrophenyl)acetamides 16a-c, succindialdehyde (13), and benzotriazole afforded enantiopure (3S,5R,7aR)-5-(1H-1,2,3-benzotriazol-1-yl)-3-substituted1-(4-nitrophenyl)tetrahydro-1H-pyrrolo[1,2-a]imidazol-2-ones 17a-c, which were converted by sodium borohydride into (3S,7aR)-3-substituted-1-(4-nitrophenyl)tetrahydro-1H-pyrrolo[1,2-a]imidazol-2-ones 18a-c. Chiral (2S)-2-amino-2-substituted-N-(4-methylphenyl)acetamides 12a-d, easily prepared in two steps from N-Boc-alpha-amino acids 10a-d, similarly reacted with glutaraldehyde (20) and benzotriazole to generate 5-benzotriazolyl-3-substituted-hexahydroimidazo[1,2-a]pyridin2(3H)-ones 21a-d, which were converted by sodium borohydride directly into optically active 3-substituted-hexahydroimidazo[1,2-a]pyridin-2(3H)-ones 22a-d.

  DOI：

  10.1021/jo010842w

文献信息

• Syntheses of Optically Active Tetrahydro-1<i>H</i>-pyrrolo[1,2-<i>a</i>]imidazol-2-ones and Hexahydroimidazo[1,2-<i>a</i>]pyridin-2(3<i>H</i>)-ones
  作者：Alan R. Katritzky、Hai-Ying He、Jing Wang

  DOI：10.1021/jo010842w

  日期：2002.7.1

  The reactions of (2S)-2-amino-2-substituted-N-(4-nitrophenyl)acetamides 16a-c, succindialdehyde (13), and benzotriazole afforded enantiopure (3S,5R,7aR)-5-(1H-1,2,3-benzotriazol-1-yl)-3-substituted1-(4-nitrophenyl)tetrahydro-1H-pyrrolo[1,2-a]imidazol-2-ones 17a-c, which were converted by sodium borohydride into (3S,7aR)-3-substituted-1-(4-nitrophenyl)tetrahydro-1H-pyrrolo[1,2-a]imidazol-2-ones 18a-c. Chiral (2S)-2-amino-2-substituted-N-(4-methylphenyl)acetamides 12a-d, easily prepared in two steps from N-Boc-alpha-amino acids 10a-d, similarly reacted with glutaraldehyde (20) and benzotriazole to generate 5-benzotriazolyl-3-substituted-hexahydroimidazo[1,2-a]pyridin2(3H)-ones 21a-d, which were converted by sodium borohydride directly into optically active 3-substituted-hexahydroimidazo[1,2-a]pyridin-2(3H)-ones 22a-d.