(2S^*,4aR^*,5S^*,8aR^*)-1-benzyl-2-(1-propyl)-(Δ-3,4)-5-hydroxy-7-oxooctahydroquinoline | 142003-58-5

• 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: (2S^*,4aR^*,5S^*,8aR^*)-1-benzyl-2-(1-propyl)-(Δ-3,4)-5-hydroxy-7-oxooctahydroquinoline
• CAS: 142003-58-5
• 化学式: C₁₉H₂₅NO₂
• 分子量: 299.413
• InChiKey: VPOSFWLYACNHNB-AITUJVMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  40.54
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2S^*,4aR^*,5S^*,8aR^*)-1-benzyl-2-(1-propyl)-(Δ-3,4)-5-hydroxy-7-oxooctahydroquinoline 在 敌草腈 、 甲基磺酰氯 、 三乙胺 作用下， 生成 (2S,4aS,8aR)-1-Benzyl-2-propyl-2,4a,8,8a-tetrahydro-1H-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：

  (2S^*,4aR^*,5S^*,8aR^*)-1-benzyl-2-(1-propyl)-(Δ-3,4)-5-(dimethylphenylsilyl)-7-oxooctahydroquinoline 生成 (2S^*,4aR^*,5S^*,8aR^*)-1-benzyl-2-(1-propyl)-(Δ-3,4)-5-hydroxy-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