(1S)-9-methyl-9-azabicyclo[4.2.1]nonan-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 英文名称: (1S)-9-methyl-9-azabicyclo[4.2.1]nonan-2-one
• 英文别名: (1S,6S)-9-methyl-9-azabicyclo[4.2.1]nonan-2-one
• 化学式: C₉H₁₅NO
• 分子量: 153.224
• InChiKey: NSXLLMSGQVUQOG-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S)-9-methyl-9-azabicyclo[4.2.1]nonan-2-one 在 盐酸 、 四(三苯基膦)钯 、 正丁基锂 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 (1S,6S)-2-(6-Chloro-pyridin-3-yl)-9-aza-bicyclo[4.2.1]non-2-ene
  参考文献：
  名称：

  Synthesis of UB-165: A novel nicotinic ligand and anatoxin-a/epibatidine hybrid

  摘要：

  UB-165 (5), a hybrid corresponding to natural anatoxin-a and epibatidine, has been synthesised and shows significant potency at the high affinity nicotine binding site in rat brain. Ent-(5) shows a much lower level of activity which parallels the sense of enantiospecificity associated with anatoxin-a. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10090-7

文献信息

• Efficient new syntheses of (+)- and (-)-anatoxin-a. Revised configuration of resolved 9-methyl-9-azabicyclo[4.2.1]nonan-2-one
  作者：John R. Ferguson、Keith W. Lumbard、Feodor Scheinmann、Andrew V. Stachulski、Peter Stjernlöf、Staffan Sundell

  DOI：10.1016/0040-4039(95)01842-6

  日期：1995.11

  the enone 7 which was converted to anatoxin-a 1 by mild acidolysis. Maintenance of chiral homogeneity from both (+)- and (-)- 2 was demonstrated by diastereomeric amide formation from (+)- and (-)-1. However, the prior correlation of(+)- 2 with (+)-1 was found to be incorrect: in fact (-)- 2 gives (+)-1.

  通过与2-氯丙腈的连续碱催化缩合和N-脱烷基化作用，双环酮2（任一对映异构体）均以高收率转化为缩水甘油腈4 。打开环氧化物，然后从所得的α-氯酮中除去HCl，得到烯酮7，该烯酮通过温和的酸解作用转化为抗毒素-a 1。由（+）-和（-）-1形成非对映异构酰胺证明了从（+）-和（-）-2两者均保持手性均一性。但是，发现（+）-2与（+）-1的先验相关性是不正确的：实际上（-）-2给出了（+）-1。
• Synthesis of UB-165: A novel nicotinic ligand and anatoxin-a/epibatidine hybrid
  作者：Emma Wright、Timothy Gallagher、Christopher G.V. Sharples、Susan Wonnacott

  DOI：10.1016/s0960-894x(97)10090-7

  日期：1997.11

  UB-165 (5), a hybrid corresponding to natural anatoxin-a and epibatidine, has been synthesised and shows significant potency at the high affinity nicotine binding site in rat brain. Ent-(5) shows a much lower level of activity which parallels the sense of enantiospecificity associated with anatoxin-a. (C) 1997 Elsevier Science Ltd.