(3aS,4S,8bS)-1-benzyl-4-methyl-1,3a,4,8b-tetrahydro-3H-imidazo[1',2':1,2]pyrrolo[3,4-c]isoxazole | 807617-99-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (3aS,4S,8bS)-1-benzyl-4-methyl-1,3a,4,8b-tetrahydro-3H-imidazo[1',2':1,2]pyrrolo[3,4-c]isoxazole
• 英文别名: (2S,6S,7S)-3-benzyl-7-methyl-4-oxa-3,8,11-triazatricyclo[6.3.0.02,6]undeca-1(11),9-diene
• CAS: 807617-99-8
• 化学式: C₁₅H₁₇N₃O
• 分子量: 255.319
• InChiKey: VCXINGCLYCOSQW-UBHSHLNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  (3aS,4S,8bS)-1-benzyl-4-methyl-1,3a,4,8b-tetrahydro-3H-imidazo[1',2':1,2]pyrrolo[3,4-c]isoxazole 在 palladium dihydroxide 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以81%的产率得到(5S,6R,7S)-(7-amino-5-methyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-6-yl)-methanol
  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-methyl-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 (3aS,4S,8bS)-1-benzyl-4-methyl-1,3a,4,8b-tetrahydro-3H-imidazo[1',2':1,2]pyrrolo[3,4-c]isoxazole
  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