(5S,6R,9S)-8-benzyl-5-isopropyl-5,6,8,9-tetrahydro-6,9-methanoimidazo[2,1-d][1,2,5]oxadiazepine | 807618-06-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (5S,6R,9S)-8-benzyl-5-isopropyl-5,6,8,9-tetrahydro-6,9-methanoimidazo[2,1-d][1,2,5]oxadiazepine
• 英文别名: (1S,7S,8R)-10-benzyl-7-propan-2-yl-9-oxa-3,6,10-triazatricyclo[6.2.1.02,6]undeca-2,4-diene
• CAS: 807618-06-0
• 化学式: C₁₇H₂₁N₃O
• 分子量: 283.373
• InChiKey: GIUMHROHGCWDAH-XHSDSOJGSA-N

物化性质

• 沸点：
  462.2±55.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  30.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5S,6R,9S)-8-benzyl-5-isopropyl-5,6,8,9-tetrahydro-6,9-methanoimidazo[2,1-d][1,2,5]oxadiazepine 在 palladium dihydroxide 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以87%的产率得到(5S,6R,8S)-8-amino-5-isopropyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-6-ol
  参考文献：
  名称：

  Intramolecular cycloadditions of nitrones derived from optically active 1-alkenyl-2-imidazolecarbaldehydes: regio- and diastereoselectivity

  摘要：

  Enantiopure polyfunctionalized imidazo[1,2-a]pyridines and pyrrolo[1,2-a]imidazoles, two classes of heterocyclic compounds including anti-inflammatories and glycosidase inhibitors, were synthesized starting from natural alpha-aminoacids and exploiting an intramolecular nitrone cycloaddition as the key step. The regiochemistry of the cycloaddition, which determines the product distribution, was markedly dependent on the R substituent and, therefore, submitted to a theoretical study by means of ab initio and MP2 calculations. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.07.065
• 作为产物：
  描述：

  (S)-1-(1-isopropyl-allyl)-1H-imidazole 在 manganese(IV) oxide 、 碳酸氢钠 、 magnesium sulfate 、 溶剂黄146 作用下， 以 氯仿 、 二甲基亚砜 、 甲苯 为溶剂， 反应 108.0h， 生成 (5S,6R,9S)-8-benzyl-5-isopropyl-5,6,8,9-tetrahydro-6,9-methanoimidazo[2,1-d][1,2,5]oxadiazepine
  参考文献：
  名称：

  Intramolecular cycloadditions of nitrones derived from optically active 1-alkenyl-2-imidazolecarbaldehydes: regio- and diastereoselectivity

  摘要：

  Enantiopure polyfunctionalized imidazo[1,2-a]pyridines and pyrrolo[1,2-a]imidazoles, two classes of heterocyclic compounds including anti-inflammatories and glycosidase inhibitors, were synthesized starting from natural alpha-aminoacids and exploiting an intramolecular nitrone cycloaddition as the key step. The regiochemistry of the cycloaddition, which determines the product distribution, was markedly dependent on the R substituent and, therefore, submitted to a theoretical study by means of ab initio and MP2 calculations. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.07.065