methyl (5S,9R)-2-ethoxy-8-hydroxy-7-methyl-11-oxo-7,8,9,10-tetrahydro-5,9-methanocycloocta[b]pyridine-5(6H)-carboxylate | 1384718-59-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: methyl (5S,9R)-2-ethoxy-8-hydroxy-7-methyl-11-oxo-7,8,9,10-tetrahydro-5,9-methanocycloocta[b]pyridine-5(6H)-carboxylate
• CAS: 1384718-59-5
• 化学式: C₁₇H₂₁NO₅
• 分子量: 319.357
• InChiKey: SIDRJRIAEQBOFC-VBDAECENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.03
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  85.72
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl (5S,9R)-2-ethoxy-8-hydroxy-7-methyl-11-oxo-7,8,9,10-tetrahydro-5,9-methanocycloocta[b]pyridine-5(6H)-carboxylate 在 4-二甲氨基吡啶 、 sodium acetate 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 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
• 作为产物：
  描述：

  2-甲基丙烯醛 、 methyl 2-ethoxy-6-hydroxy-7,8-dihydroquinoline-5-carboxylate 在 C₂₈H₃₈N₄OS 、 苯甲酸 、 四甲基胍 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 36.0h， 生成 methyl (5S,9R)-2-ethoxy-8-hydroxy-7-methyl-11-oxo-7,8,9,10-tetrahydro-5,9-methanocycloocta[b]pyridine-5(6H)-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