[(13E)-13-ethylidene-5-methoxy-11-methyl-6-azatricyclo[7.3.1.02,7]trideca-2(7),3,5,10-tetraen-1-yl]methyl methanesulfonate | 134287-19-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(13E)-13-ethylidene-5-methoxy-11-methyl-6-azatricyclo[7.3.1.02,7]trideca-2(7),3,5,10-tetraen-1-yl]methyl methanesulfonate
• CAS: 134287-19-7
• 化学式: C₁₈H₂₃NO₄S
• 分子量: 349.451
• InChiKey: WLMGCTWQWQXCII-LHHJGKSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65.49
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [(13E)-13-ethylidene-5-methoxy-11-methyl-6-azatricyclo[7.3.1.02,7]trideca-2(7),3,5,10-tetraen-1-yl]methyl methanesulfonate 在 18-冠醚-6 lithium aluminium tetrahydride 、 sodium azide 、 碘代三甲硅烷 、 三乙胺 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 二氯甲烷 、 氯仿 为溶剂， 反应 38.0h， 生成 (13E)-1-(aminomethyl)-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.02,7]trideca-2(7),3,10-trien-5-one
  参考文献：
  名称：

  Synthesis of huperzine A, its analogs, and their anticholinesterase activity

  摘要：

  Huperzine A is a new alkaloid isolated from the club moss Huperzia serrata (Thunb.) Trev., a Chinese folk medicine. This alkaloid exhibits potent activity as an inhibitor of acetylcholinesterase. Consequently, the compound is presently being investigated in China for the treatment of individuals suffering from various forms of memory impairment including Alzheimer's dementia. Details of the total synthesis of (+/-)-huperzine A are described as well as the preparation of a variety of huperzine analogues including its presumed pharmacophore. The extent of these new compounds to inhibit acetylcholinesterase is presented along with a discussion of the effects of the structural changes on biological activity.

  DOI：

  10.1021/jo00015a014
• 作为产物：
  描述：

  1-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)pyrrolidine 在 4-二甲氨基吡啶 、 palladium hydroxide - carbon 盐酸 、 lithium aluminium tetrahydride 、 偶氮二异丁腈 、 氢气 、 sodium acetate 、 potassium hydride 、 三乙胺 、 silver carbonate 、 四甲基胍 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 溶剂黄146 、 丙酮 为溶剂， 反应 102.0h， 生成 [(13E)-13-ethylidene-5-methoxy-11-methyl-6-azatricyclo[7.3.1.02,7]trideca-2(7),3,5,10-tetraen-1-yl]methyl methanesulfonate
  参考文献：
  名称：

  Synthesis of huperzine A, its analogs, and their anticholinesterase activity

  摘要：

  Huperzine A is a new alkaloid isolated from the club moss Huperzia serrata (Thunb.) Trev., a Chinese folk medicine. This alkaloid exhibits potent activity as an inhibitor of acetylcholinesterase. Consequently, the compound is presently being investigated in China for the treatment of individuals suffering from various forms of memory impairment including Alzheimer's dementia. Details of the total synthesis of (+/-)-huperzine A are described as well as the preparation of a variety of huperzine analogues including its presumed pharmacophore. The extent of these new compounds to inhibit acetylcholinesterase is presented along with a discussion of the effects of the structural changes on biological activity.

  DOI：

  10.1021/jo00015a014

文献信息

• KOZIKOWSKI, ALAN P.;XIA, YAN;REDDY, E. RAJARATHNAM;TUCKMANTEL, WERNER;HAN+, J. ORG. CHEM., 56,(1991) N5, C. 4636-4645
  作者：KOZIKOWSKI, ALAN P.、XIA, YAN、REDDY, E. RAJARATHNAM、TUCKMANTEL, WERNER、HAN+

  DOI：——

  日期：——