(2S^*,4aR^*,5S^*,8aR^*)-1-methyl-2-(1-propyl)-(Δ-3,4)-5-(dimethylphenylsilyl)-7-oxooctahydroquinoline | 142003-51-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2S^*,4aR^*,5S^*,8aR^*)-1-methyl-2-(1-propyl)-(Δ-3,4)-5-(dimethylphenylsilyl)-7-oxooctahydroquinoline
• CAS: 142003-51-8
• 化学式: C₂₁H₃₁NOSi
• 分子量: 341.569
• InChiKey: REKDWKXOLODOSH-ZXNZYJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2S^*,4aR^*,5S^*,8aR^*)-1-methyl-2-(1-propyl)-(Δ-3,4)-5-(dimethylphenylsilyl)-7-oxooctahydroquinoline 在 palladium on activated charcoal 四氟硼酸-二乙醚络合物 、 potassium fluoride 、 氢气 、 双氧水 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 25.0~40.0 ℃ 、101.33 kPa 条件下， 反应 8.42h， 生成 (2S,4aS,5R,8aS)-5-Hydroxy-1-methyl-2-propyl-octahydro-quinolin-7-one
  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：

  (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 在 potassium hydride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 8.0h， 以64%的产率得到(2S^*,4aR^*,5S^*,8aR^*)-1-methyl-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