(2R^*,4aS^*,5S^*,8aR^*)-1-methyl-2-(1-propyl)-5-methyl-(Δ-6,7)-7-<(trifluoromethanesulfonyl)oxy>decahydroquinoline | 142003-56-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (2R^*,4aS^*,5S^*,8aR^*)-1-methyl-2-(1-propyl)-5-methyl-(Δ-6,7)-7-<(trifluoromethanesulfonyl)oxy>decahydroquinoline
• CAS: 142003-56-3
• 化学式: C₁₅H₂₄F₃NO₃S
• 分子量: 355.422
• InChiKey: YDJWDMOCYGEMNV-VTPLQMEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R^*,4aS^*,5S^*,8aR^*)-1-methyl-2-(1-propyl)-5-methyl-(Δ-6,7)-7-<(trifluoromethanesulfonyl)oxy>decahydroquinoline 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以62%的产率得到(2R^*,4aS^*,5S^*,8aR^*)-1-methyl-2-(1-propyl)-5-methyldecahydroquinoline
  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：

  N-苯基双(三氟甲烷磺酰)亚胺 、 (2R,4aS,8aR)-1-Methyl-2-propyl-2,3,4,4a,8,8a-hexahydro-1H-quinolin-7-one 、 alkaline earth salt of/the/ methylsulfuric acid 生成 (2R^*,4aS^*,5S^*,8aR^*)-1-methyl-2-(1-propyl)-5-methyl-(Δ-6,7)-7-<(trifluoromethanesulfonyl)oxy>decahydroquinoline
  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