(S)-2-Propyl-3,4-dihydro-2H-pyridine-1-carboxylic acid methyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (S)-2-Propyl-3,4-dihydro-2H-pyridine-1-carboxylic acid methyl ester
• 英文别名: methyl (2S)-2-propyl-3,4-dihydro-2H-pyridine-1-carboxylate
• 化学式: C₁₀H₁₇NO₂
• 分子量: 183.25
• InChiKey: RLFJNCDNGMFPGA-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-Propyl-3,4-dihydro-2H-pyridine-1-carboxylic acid methyl ester 在 sodium hydroxide 、 dimethyl sulfide borane 、 水 、 双氧水 作用下， 生成 (2S,5R)-5-Hydroxy-2-propyl-piperidine-1-carboxylic acid methyl ester 、 Methyl (2S,5S)-5-hydroxy-2-propylpiperidine-1-carboxylate
  参考文献：
  名称：

  Enantioselective preparation and hydroboration of cyclic enamides: Synthesis of (2S)-pseudoconhydrine

  摘要：

  Successive treatment of 2-alkyl-1-hydroxy-6-carbonylsultampiperidines 1 with NaH and an acylating agent/pyridine in boiling toluene affords optically pure 1-acyl-2-alkyl-1,2,3,4-tetrahydropyridines 2. Hydroboration/oxidation of N-benzoylenamides 2f and 2g furnishes trans-2-alkyl-1-benzyl-5-hydroxypiperidines 5f and 5g, respectively. Hydrogenolysis of 5f provides pure (2S)-pseudoconhydrine (7), in 3 steps from 1, R(2)=n-C3H7 (31% overall yield).

  DOI：

  10.1016/0040-4039(95)00439-j
• 作为产物：
  描述：

  氯甲酸甲酯 、 ((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-((2S,6S)-1-hydroxy-6-propyl-piperidin-2-yl)-methanone 在 2,3,5-三甲基吡啶 、 sodium hydride 作用下， 生成 (S)-2-Propyl-3,4-dihydro-2H-pyridine-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Enantioselective preparation and hydroboration of cyclic enamides: Synthesis of (2S)-pseudoconhydrine

  摘要：

  Successive treatment of 2-alkyl-1-hydroxy-6-carbonylsultampiperidines 1 with NaH and an acylating agent/pyridine in boiling toluene affords optically pure 1-acyl-2-alkyl-1,2,3,4-tetrahydropyridines 2. Hydroboration/oxidation of N-benzoylenamides 2f and 2g furnishes trans-2-alkyl-1-benzyl-5-hydroxypiperidines 5f and 5g, respectively. Hydrogenolysis of 5f provides pure (2S)-pseudoconhydrine (7), in 3 steps from 1, R(2)=n-C3H7 (31% overall yield).

  DOI：

  10.1016/0040-4039(95)00439-j

文献信息

• Enantioselective preparation and hydroboration of cyclic enamides: Synthesis of (2S)-pseudoconhydrine
  作者：Wolfgang Oppolzer、Christian G Bochet

  DOI：10.1016/0040-4039(95)00439-j

  日期：1995.4

  Successive treatment of 2-alkyl-1-hydroxy-6-carbonylsultampiperidines 1 with NaH and an acylating agent/pyridine in boiling toluene affords optically pure 1-acyl-2-alkyl-1,2,3,4-tetrahydropyridines 2. Hydroboration/oxidation of N-benzoylenamides 2f and 2g furnishes trans-2-alkyl-1-benzyl-5-hydroxypiperidines 5f and 5g, respectively. Hydrogenolysis of 5f provides pure (2S)-pseudoconhydrine (7), in 3 steps from 1, R(2)=n-C3H7 (31% overall yield).