lycoperine A | 873868-50-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: lycoperine A
• 英文别名: diacetylhupercumine B；1-[(7R,8aR)-5-[[(2S,6R)-6-[[(7R,8aR)-1-acetyl-7-methyl-3,4,6,7,8,8a-hexahydro-2H-quinolin-5-yl]methyl]piperidin-2-yl]methyl]-7-methyl-3,4,6,7,8,8a-hexahydro-2H-quinolin-1-yl]ethanone
• CAS: 873868-50-9
• 化学式: C₃₁H₄₉N₃O₂
• 分子量: 495.749
• InChiKey: WDJDPNAURLPQIO-ZHHATGKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  52.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  lycoperine A 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以72%的产率得到
  参考文献：
  名称：

  Total Synthesis of (−)-Lycoperine A

  摘要：

  Lycoperine A was synthesized through a highly convergent route in which a double alkylation of 2,6-dicyano-N-benzylpiperidine with the octahydroquinoline moiety gave the lycoperine skeleton. The octahydroquinoline was prepared by a desymmetrization reaction of 5-methylcyclohexane-1,3-dione. Hydrolysis, reductive amination, and cyclization gave lycoperine A in 13 steps and 3% overall yield. The absolute configuration of lycoperine A was assigned as 6R,6'R,8R,8'R,13S,17R.

  DOI：

  10.1021/ol902389e
• 作为产物：
  描述：

  1,7-bis((7R,8aR)-1-ethanoyl-7-methyl-1,2,3,4,6,7,8,8a-octahydroquinolin-5-yl)heptane-2,6-dione 在 三氟乙酸铵 、 三乙酰氧基硼氢化钠 、 sodium methoxide-d3 作用下， 以 四氢呋喃 、 氘代甲醇 为溶剂， 反应 144.0h， 以29%的产率得到lycoperine A
  参考文献：
  名称：

  Total Synthesis of (−)-Lycoperine A

  摘要：

  Lycoperine A was synthesized through a highly convergent route in which a double alkylation of 2,6-dicyano-N-benzylpiperidine with the octahydroquinoline moiety gave the lycoperine skeleton. The octahydroquinoline was prepared by a desymmetrization reaction of 5-methylcyclohexane-1,3-dione. Hydrolysis, reductive amination, and cyclization gave lycoperine A in 13 steps and 3% overall yield. The absolute configuration of lycoperine A was assigned as 6R,6'R,8R,8'R,13S,17R.

  DOI：

  10.1021/ol902389e

文献信息

• Hupercumines A and B, <i>Lycopodium</i> Alkaloids from <i>Huperzia cunninghamioides</i>, Inhibiting Acetylcholinesterase
  作者：Yusuke Hirasawa、Chiho Mitsui、Nahoko Uchiyama、Takashi Hakamatsuka、Hiroshi Morita

  DOI：10.1021/acs.orglett.8b00152

  日期：2018.3.2

  A novel class of C38N4Lycopodium alkaloid, hupercumine A (1), consisting of two octahydroquinolines, a decahydroquinoline, and a piperidine, and a new C27N3-type alkaloid, hupercumine B (2), were isolated from Huperzia cunninghamioides (Hayata) Holub. The structures and absolute configurations of 1 and 2 were elucidated on the basis of spectroscopic data, chemical means, and biogenetic point of view

  从石杉属植物中分离出新型的C 38 N 4石蒜生物碱石杉碱A（1），由两个八氢喹啉，十氢喹啉和哌啶组成，以及新的C 27 N 3型生物碱石杉碱B（2）。cunninghamioides（早aya）Holub。根据光谱数据，化学方法和生物遗传学角度阐明了1和2的结构和绝对构型。石杉碱甲（1）和乙（2）显示出对乙酰胆碱酯酶的中等抑制活性。
• Total Synthesis of (−)-Lycoperine A
  作者：Yoshitaka Nakamura、Anthony M. Burke、Shunsuke Kotani、Joseph W. Ziller、Scott D. Rychnovsky

  DOI：10.1021/ol902389e

  日期：2010.1.1

  Lycoperine A was synthesized through a highly convergent route in which a double alkylation of 2,6-dicyano-N-benzylpiperidine with the octahydroquinoline moiety gave the lycoperine skeleton. The octahydroquinoline was prepared by a desymmetrization reaction of 5-methylcyclohexane-1,3-dione. Hydrolysis, reductive amination, and cyclization gave lycoperine A in 13 steps and 3% overall yield. The absolute configuration of lycoperine A was assigned as 6R,6'R,8R,8'R,13S,17R.