(1R*,3S*,4S*)-2-methyl-3-(1-propyl)-8,8-dimethoxy-2-azabicyclo<2.2.2>oct-5-ene | 142003-49-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R*,3S*,4S*)-2-methyl-3-(1-propyl)-8,8-dimethoxy-2-azabicyclo<2.2.2>oct-5-ene
• 英文别名: (1R^*,3S^*,4S^*)-2-methyl-3-(1-propyl)-8,8-dimethoxy-2-azabicyclo<2.2.2>oct-5-ene
• CAS: 142003-49-4
• 化学式: C₁₃H₂₃NO₂
• 分子量: 225.331
• InChiKey: YQTSZYKFJIEMLR-IJLUTSLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.03
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  21.7
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1R*,3S*,4S*)-2-methyl-3-(1-propyl)-8,8-dimethoxy-2-azabicyclo<2.2.2>oct-5-ene 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 (1R^*,3S^*,4S^*,5S^*)-2-methyl-3-(1-propyl)-5-<(E)-2-(dimethylphenylsilyl)-1-ethenyl>-2-azabicyclo<2.2.2>oct-7-en-5-ol
  参考文献：
  名称：

  Stereospecific total syntheses of decahydroquinoline alkaloids (.+-.)-195A and (.+-.)-2-epi-195A

  摘要：

  The total syntheses of decahydroquinoline alkaloids (+/-)-195A (pumiliotoxin C) and (+/-)-2-epi-195A are described. An unexpected, stereospecific epimerization of the C2 stereocenter of intermediate 6a occurred during its reduction. The isomerization resulted in ultimate production of 2-epi-195A. The stereochemical relationship of the C2, C4a, C5, and C8a stereocenters in 2-epi-195A is common to other decahydroquinoline alkaloids and gephyrotoxin. The 2-epi-195A synthesis demonstrated the viability of an N-Me group as a nitrogen protecting group. Alkaloid 195A was prepared in 5.0% overall yield by minor modification of the protocol established in the 2-epi-195A synthesis.

  DOI：

  10.1021/jo00041a012
• 作为产物：
  描述：

  4-甲氧基吡啶 在 lithium aluminium tetrahydride 、 sodium amalgam 、 camphor-10-sulfonic acid 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 153.75h， 生成 (1R*,3S*,4S*)-2-methyl-3-(1-propyl)-8,8-dimethoxy-2-azabicyclo<2.2.2>oct-5-ene
  参考文献：
  名称：

  Stereospecific total syntheses of decahydroquinoline alkaloids (.+-.)-195A and (.+-.)-2-epi-195A

  摘要：

  The total syntheses of decahydroquinoline alkaloids (+/-)-195A (pumiliotoxin C) and (+/-)-2-epi-195A are described. An unexpected, stereospecific epimerization of the C2 stereocenter of intermediate 6a occurred during its reduction. The isomerization resulted in ultimate production of 2-epi-195A. The stereochemical relationship of the C2, C4a, C5, and C8a stereocenters in 2-epi-195A is common to other decahydroquinoline alkaloids and gephyrotoxin. The 2-epi-195A synthesis demonstrated the viability of an N-Me group as a nitrogen protecting group. Alkaloid 195A was prepared in 5.0% overall yield by minor modification of the protocol established in the 2-epi-195A synthesis.

  DOI：

  10.1021/jo00041a012