[(1R,9R)-13-Eth-(E)-ylidene-5-methoxy-11-methyl-6-aza-tricyclo[7.3.1.0^2,7]trideca-2(7),3,5,10-tetraen-1-yl]-methanol | 307495-98-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(1R,9R)-13-Eth-(E)-ylidene-5-methoxy-11-methyl-6-aza-tricyclo[7.3.1.0^2,7]trideca-2(7),3,5,10-tetraen-1-yl]-methanol
• 英文别名: [(1R,9R,13E)-13-ethylidene-5-methoxy-11-methyl-6-azatricyclo[7.3.1.02,7]trideca-2(7),3,5,10-tetraen-1-yl]methanol
• CAS: 307495-98-3
• 化学式: C₁₇H₂₁NO₂
• 分子量: 271.359
• InChiKey: UGQWVMXSCVRFLX-QNDFORTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  42.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(1R,9R)-13-Eth-(E)-ylidene-5-methoxy-11-methyl-6-aza-tricyclo[7.3.1.0^2,7]trideca-2(7),3,5,10-tetraen-1-yl]-methanol 在 草酰氯 、 二甲基亚砜 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 1-[(1R,9R)-13-Eth-(E)-ylidene-5-methoxy-11-methyl-6-aza-tricyclo[7.3.1.0^2,7]trideca-2(7),3,5,10-tetraen-1-yl]-ethanone
  参考文献：
  名称：

  Synthesis of 5-substituted analogues of huperzine A

  摘要：

  Three 5-isosteres of huperzine A (2-4) were first synthesized. The key intermediate 10 was prepared by the reaction of acid 13 with LTA. The compounds 2 and 3 had 50% inhibition by 35 and 47 mu M, respectively, which still retained anti-acetylcholinesterase activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00408-x
• 作为产物：
  描述：

  (1R,9R)-13-Eth-(E)-ylidene-5-methoxy-11-methyl-6-aza-tricyclo[7.3.1.0^2,7]trideca-2(7),3,5,10-tetraene-1-carboxylic acid methyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到[(1R,9R)-13-Eth-(E)-ylidene-5-methoxy-11-methyl-6-aza-tricyclo[7.3.1.0^2,7]trideca-2(7),3,5,10-tetraen-1-yl]-methanol
  参考文献：
  名称：

  Synthesis of 5-substituted analogues of huperzine A

  摘要：

  Three 5-isosteres of huperzine A (2-4) were first synthesized. The key intermediate 10 was prepared by the reaction of acid 13 with LTA. The compounds 2 and 3 had 50% inhibition by 35 and 47 mu M, respectively, which still retained anti-acetylcholinesterase activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00408-x