(1R^*,3S^*,4S^*,5S^*)-2-benzyl-3-(1-propyl)-5-<(E)-2-(dimethylphenylsilyl)-1-ethenyl>-2-azabicyclo<2.2.2>oct-7-en-5-ol | 142003-69-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R^*,3S^*,4S^*,5S^*)-2-benzyl-3-(1-propyl)-5-<(E)-2-(dimethylphenylsilyl)-1-ethenyl>-2-azabicyclo<2.2.2>oct-7-en-5-ol
• 英文别名: (1R^*,3S^*,4S^*,5S^*)-2-benzyl-3-(1-propyl)-5-[(E)-2-(dimethylphenylsilyl)-1-ethenyl]-2-azabicyclo[2.2.2]oct-7-en-5-ol；(1R,3S,4S,5S)-2-benzyl-5-[(E)-2-[dimethyl(phenyl)silyl]ethenyl]-3-propyl-2-azabicyclo[2.2.2]oct-7-en-5-ol
• CAS: 142003-69-8
• 化学式: C₂₇H₃₅NOSi
• 分子量: 417.666
• InChiKey: ULQZEDNDTOBITL-MNLQOWJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  23.47
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1R^*,3S^*,4S^*,5S^*)-2-benzyl-3-(1-propyl)-5-<(E)-2-(dimethylphenylsilyl)-1-ethenyl>-2-azabicyclo<2.2.2>oct-7-en-5-ol 在 potassium hydride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 8.5h， 以79%的产率得到(2S^*,4aR^*,5S^*,8aR^*)-1-benzyl-2-(1-propyl)-(Δ-3,4)-5-(dimethylphenylsilyl)-7-oxooctahydroquinoline
  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 盐酸 、 lithium aluminium tetrahydride 、 正丁基锂 、 sodium amalgam 、 camphor-10-sulfonic acid 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 149.33h， 生成 (1R^*,3S^*,4S^*,5S^*)-2-benzyl-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