methyl (5S,9R)-8-hydroxy-3-methoxy-7-methyl-11-oxo-7,8,9,10-tetrahydro-5,9-methanobenzo[8]annulene-5(6H)-carboxylate | 1384718-90-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl (5S,9R)-8-hydroxy-3-methoxy-7-methyl-11-oxo-7,8,9,10-tetrahydro-5,9-methanobenzo[8]annulene-5(6H)-carboxylate
• CAS: 1384718-90-4
• 化学式: C₁₇H₂₀O₅
• 分子量: 304.343
• InChiKey: JBJCWPTWOAALCH-PHKHPWRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.25
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (5S,9R)-8-hydroxy-3-methoxy-7-methyl-11-oxo-7,8,9,10-tetrahydro-5,9-methanobenzo[8]annulene-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 (5SR,9RS)-methyl 3-methoxy-7-methyl-11-oxo-5,6,9,10-tetrahydro-5,9-methano-benzo[8]annulene-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：

  7-甲氧基-2-萘满酮 在 C₂₈H₃₈N₄OS 、 sodium hydride 、 苯甲酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 36.0h， 生成 methyl (5S,9R)-8-hydroxy-3-methoxy-7-methyl-11-oxo-7,8,9,10-tetrahydro-5,9-methanobenzo[8]annulene-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