(S)-1-(1-isopropyl-allyl)-1H-imidazole-2-carbaldehyde | 807618-04-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-1-(1-isopropyl-allyl)-1H-imidazole-2-carbaldehyde
• CAS: 807618-04-8
• 化学式: C₁₀H₁₄N₂O
• 分子量: 178.234
• InChiKey: XHDLVMGWQOMJRT-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  34.89
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-1-(1-isopropyl-allyl)-1H-imidazole-2-carbaldehyde 在 palladium dihydroxide 盐酸 、 氢气 、 碳酸氢钠 、 magnesium sulfate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 48.0h， 生成 (5S,6R,7S)-(7-amino-5-isopropyl-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：

  2-甲基-2-丙基[(3S)-4-甲基-1-戊烯-3-基]氨基甲酸酯 在 manganese(IV) oxide 、 磷酸 、 ammonium chloride 、 溶剂黄146 、 三氟乙酸 作用下， 以 氯仿 、 水 、 二甲基亚砜 为溶剂， 反应 86.5h， 生成 (S)-1-(1-isopropyl-allyl)-1H-imidazole-2-carbaldehyde
  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