4-Oxo-3,4-dihydro-2H-pyridine-1-carboxylic acid (1R,2S,5R)-2-[1-(4-methoxy-phenyl)-1-methyl-ethyl]-5-methyl-cyclohexyl ester | 186045-49-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-Oxo-3,4-dihydro-2H-pyridine-1-carboxylic acid (1R,2S,5R)-2-[1-(4-methoxy-phenyl)-1-methyl-ethyl]-5-methyl-cyclohexyl ester
• 英文别名: [(1R,2S,5R)-2-[2-(4-methoxyphenyl)propan-2-yl]-5-methylcyclohexyl] 4-oxo-2,3-dihydropyridine-1-carboxylate
• CAS: 186045-49-8
• 化学式: C₂₃H₃₁NO₄
• 分子量: 385.503
• InChiKey: MDYQCYRPULZTNA-MAODMQOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-Oxo-3,4-dihydro-2H-pyridine-1-carboxylic acid (1R,2S,5R)-2-[1-(4-methoxy-phenyl)-1-methyl-ethyl]-5-methyl-cyclohexyl ester 、 烯丙基三甲基硅烷 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-2-Allyl-4-oxo-piperidine-1-carboxylic acid (1R,2S,5R)-2-[1-(4-methoxy-phenyl)-1-methyl-ethyl]-5-methyl-cyclohexyl ester 、 (S)-2-Allyl-4-oxo-piperidine-1-carboxylic acid (1R,2S,5R)-2-[1-(4-methoxy-phenyl)-1-methyl-ethyl]-5-methyl-cyclohexyl ester
  参考文献：
  名称：

  Lewis acid-promoted asymmetric conjugate allylation of N-acyl-2,3-dihydro-4-pyridones induced by intramolecular π interactions

  摘要：

  Lewis acid-promoted conjugate addition reaction of an allylsilane to a series of the chiral 8-arylmenthol-derived N-acyl-2,3-dihydro-4-pyridones leads to the 2-allyl-4-piperidones with moderate to high levels of asymmetric induction, indicating restacking contribution to chirality control. This methodology was applied to the asymmetric synthesis of (-)-N-methylconiine. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02129-6
• 作为产物：
  描述：

  1,4-Dioxa-8-aza-spiro[4.5]dec-6-ene-8-carboxylic acid (1R,2S,5R)-2-[1-(4-methoxy-phenyl)-1-methyl-ethyl]-5-methyl-cyclohexyl ester 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 生成 4-Oxo-3,4-dihydro-2H-pyridine-1-carboxylic acid (1R,2S,5R)-2-[1-(4-methoxy-phenyl)-1-methyl-ethyl]-5-methyl-cyclohexyl ester
  参考文献：
  名称：

  Lewis acid-promoted asymmetric conjugate allylation of N-acyl-2,3-dihydro-4-pyridones induced by intramolecular π interactions

  摘要：

  Lewis acid-promoted conjugate addition reaction of an allylsilane to a series of the chiral 8-arylmenthol-derived N-acyl-2,3-dihydro-4-pyridones leads to the 2-allyl-4-piperidones with moderate to high levels of asymmetric induction, indicating restacking contribution to chirality control. This methodology was applied to the asymmetric synthesis of (-)-N-methylconiine. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02129-6