(+/-)-9,10-dihydro-2-methoxy-7-methyl-11-oxo-5,9-methanocyclooctapyridine-5(6H)-carboxylic acid methyl ester | 120686-02-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-9,10-dihydro-2-methoxy-7-methyl-11-oxo-5,9-methanocyclooctapyridine-5(6H)-carboxylic acid methyl ester
• 英文别名: (+/-)-9,10-dihydro-2-methoxy-7-methyl-11-oxo-5,9-methanocycloocta[b]pyridine-5(6H)-carboxylic acid methyl ester；Methyl 5-methoxy-11-methyl-13-oxo-6-azatricyclo[7.3.1.02,7]trideca-2(7),3,5,10-tetraene-1-carboxylate
• CAS: 120686-02-4
• 化学式: C₁₆H₁₇NO₄
• 分子量: 287.315
• InChiKey: QTUFAPSOCWPKOH-UHFFFAOYSA-N

物化性质

• 熔点：
  123 °C
• 沸点：
  388.9±42.0 °C(Predicted)
• 密度：
  1.260±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-9,10-dihydro-2-methoxy-7-methyl-11-oxo-5,9-methanocyclooctapyridine-5(6H)-carboxylic acid methyl ester 在 氯化亚砜 、 sodium azide 、 lithium thiopropiolate 作用下， 以 六甲基磷酰三胺 、 甲苯 为溶剂， 反应 36.0h， 生成 [13-Eth-(Z)-ylidene-5-methoxy-11-methyl-6-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5,10-tetraen-1-yl]-carbamic acid methyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of (±)-Z-huperzine A

  摘要：

  DOI：

  10.1016/s0040-4039(00)97013-8
• 作为产物：
  描述：

  1,4-环己二酮单乙二醇缩酮 在 4-二甲氨基吡啶 、 palladium hydroxide - carbon 盐酸 、 氢气 、 sodium acetate 、 potassium hydride 、 对甲苯磺酸 、 三乙胺 、 silver carbonate 、 四甲基胍 作用下， 以 二氯甲烷 、 氯仿 、 溶剂黄146 、 丙酮 、 苯 为溶剂， 反应 69.0h， 生成 (+/-)-9,10-dihydro-2-methoxy-7-methyl-11-oxo-5,9-methanocyclooctapyridine-5(6H)-carboxylic acid methyl ester
  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

• An improved synthetic route to huperzine A; new analogues and their inhibition of acetylcholinesterase
  作者：Alan P. Kozikowski、Giuseppe Campiani、Patricia Aagaard、Michael McKinney

  DOI：10.1039/c39930000860

  日期：——

  A bicycloannulation approach to huperzine A is detailed together with syntheses of the methylene analogue 8, the diamino compound 12 and their inhibition of acetylcholinesterase.

  文中详细介绍了一种双环化方法制备胡朴素 A，以及亚甲基类似物 8 和二氨基化合物 12 的合成及其对乙酰胆碱酯酶的抑制作用。
• Synthetic chemistry, neurotransmission and second messengers
  作者：Alan P. Kozikowski

  DOI：10.1002/jhet.5570270108

  日期：1990.1
• QIAN, LIGANG;RUYUN, JI, TETRAHEDRON LETT., 30,(1989) N6, C. 2089-2090
  作者：QIAN, LIGANG、RUYUN, JI

  DOI：——

  日期：——
• 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：——
• METHODS OF RESOLVING RACEMIC MIXTURE TO OBTAIN (-)-HUPERZINE A
  申请人：AMPHASTAR PHARMACEUTICALS INC.

  公开号：US20160096808A1

  公开（公告）日：2016-04-07

  A method of resolving a racemic mixture of (±)-Huperzine A to (−)-Huperzine A includes: separating the (−)-Huperzine A from the racemic mixture of (±)-Huperzine A by chiral high performance liquid chromatography (HPLC), the chiral HPLC being performed utilizing a mobile phase including a solution including an alcohol and one selected from dichloromethane, trichloromethane, and a mixture thereof, and the chiral HPLC being performed utilizing a chiral stationary phase including a polysaccharide derivative.