(5S,9R)-methyl 2-ethoxy-7-methyl-11-oxo-5,6,9,10-tetrahydro-5,9-methano-cycloocta[b]pyridine-5-carboxylate | 1384718-67-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5S,9R)-methyl 2-ethoxy-7-methyl-11-oxo-5,6,9,10-tetrahydro-5,9-methano-cycloocta[b]pyridine-5-carboxylate
• 英文别名: methyl (1S,9R)-5-ethoxy-11-methyl-13-oxo-6-azatricyclo[7.3.1.02,7]trideca-2(7),3,5,10-tetraene-1-carboxylate
• CAS: 1384718-67-5
• 化学式: C₁₇H₁₉NO₄
• 分子量: 301.342
• InChiKey: BRZYMDMEVDISCR-GTNSWQLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 sodium acetate 、 溶剂黄146 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 24.0h， 生成 (5S,9R)-methyl 2-ethoxy-7-methyl-11-oxo-5,6,9,10-tetrahydro-5,9-methano-cycloocta[b]pyridine-5-carboxylate
  参考文献：
  名称：

  Target-oriented multifunctional organocatalysis for enantioselective synthesis of bicyclo[3.3.1]nona-2,6-dien-9-ones. A formal asymmetric synthesis of huperzine A

  摘要：

  A target-oriented highly enantioselective multifunctional organocatalytic approach has been developed to construct the bicycle-[3.3.1]nona-2,6-dien-9-one core of (-)-huperzine A for the first time, with up to 95% ee in the gram-scale procedure. The newly established methodology is also eligible to synthesize a variety of bicyclo[3.3.1]nona-2,6-dien-9-ones in high enantiopurities, and thus is useful for the future development of novel huperzine A analogs with medicinal interests. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.061