(3aR,8aS)-N-((R)-4-isopropyl-4,5-dihydrooxazol-2-yl)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-amine | 1246680-03-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (3aR,8aS)-N-((R)-4-isopropyl-4,5-dihydrooxazol-2-yl)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-amine
• CAS: 1246680-03-4
• 化学式: C₁₆H₁₉N₃O₂
• 分子量: 285.346
• InChiKey: ONQPSLOOHWPJAJ-MELADBBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.04
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.21
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3aR,8aS)-N-((R)-4-isopropyl-4,5-dihydrooxazol-2-yl)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-amine 、 溴甲苯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.17h， 以70%的产率得到(3aR,8aS)-N-benzyl-N-((R)-4-isopropyl-4,5-dihydrooxazol-2-yl)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-amine
  参考文献：
  名称：

  Development of Bifunctional Aza-Bis(oxazoline) Copper Catalysts for Enantioselective Henry Reaction

  摘要：

  Base-functionalized aza-bis(oxazoline) ligands were prepared to explore the concept of dual activation through the Lewis acid and a tethered tertiary amine base, The catalytic activity of the Cu complex was evaluated for the asymmetric Henry reaction. Compared with a corresponding unfunctionalized copper complex with external 1-benzyl-4-ethylpiperazine base, the ethylpiperazine-functionalized aza-bis(oxazoline) copper catalyst resulted in rate acceleration (2.5 times) as well as improved enantioselectivity (72% ee vs 92% ee).

  DOI：

  10.1021/jo1009867
• 作为产物：
  描述：

  (R)-4-isopropyl-4,5-dihydrooxazol-2-amine 、 (3aR,8aS)-2-ethoxy-8,8a-dihydro-3aH-indeno[1,2-d]oxazole 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以40%的产率得到(3aR,8aS)-N-((R)-4-isopropyl-4,5-dihydrooxazol-2-yl)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-amine
  参考文献：
  名称：

  Development of Bifunctional Aza-Bis(oxazoline) Copper Catalysts for Enantioselective Henry Reaction

  摘要：

  Base-functionalized aza-bis(oxazoline) ligands were prepared to explore the concept of dual activation through the Lewis acid and a tethered tertiary amine base, The catalytic activity of the Cu complex was evaluated for the asymmetric Henry reaction. Compared with a corresponding unfunctionalized copper complex with external 1-benzyl-4-ethylpiperazine base, the ethylpiperazine-functionalized aza-bis(oxazoline) copper catalyst resulted in rate acceleration (2.5 times) as well as improved enantioselectivity (72% ee vs 92% ee).

  DOI：

  10.1021/jo1009867