(3aR,8aS)-2-ethoxy-8,8a-dihydro-3aH-indeno[1,2-d]oxazole | 1246679-95-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (3aR,8aS)-2-ethoxy-8,8a-dihydro-3aH-indeno[1,2-d]oxazole
• CAS: 1246679-95-7
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: LQOLSCNMTSVTTN-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  30.82
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  triethyloxonium fluoroborate 、 (3AR-顺)-(+)-3,3A,8,8A-四氢-2H-茚并[1,2-D]噁唑-2-酮 以 二氯甲烷 为溶剂， 以95%的产率得到(3aR,8aS)-2-ethoxy-8,8a-dihydro-3aH-indeno[1,2-d]oxazole
  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