6-Chloro-2-(4-methoxy-phenyl)-5-methyl-nicotinic acid methyl ester | 197235-04-4

• 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: 6-Chloro-2-(4-methoxy-phenyl)-5-methyl-nicotinic acid methyl ester
• CAS: 197235-04-4
• 化学式: C₁₅H₁₄ClNO₃
• 分子量: 291.734
• InChiKey: FRNKXUNODLNWRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  48.42
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6-Chloro-2-(4-methoxy-phenyl)-5-methyl-nicotinic acid methyl ester 在 platinum(IV) oxide 、 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 溶剂黄146 为溶剂， 生成 (2S,3R,5S)-2-(4-Methoxy-phenyl)-5-methyl-piperidine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Generation of 3-piperidine(methan)amines and cyclic 3-piperidine-methanamines as potential substance P antagonists

  摘要：

  A general method is described for the synthesis of 3-piperidine(methan)amines and their cyclic analogues. The 3,5-dichloro-2H-1,4-oxazin-2-ones 6 and 3-aryl substituted analogues are reacted with acetylenic dienophiles yielding pyridines. Further catalytic hydrogenation and functional group transformation (1) or substitution (2-3) with ring closure reactions (4) followed by hydrogenation provided the 2,3,5-cis substituted piperidines 1-3 and a cis substituted [3,4-c]pyrrolopiperidine 4. These compounds have recently raised great interest due to their Substance P antagonist profiles. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00791-6
• 作为产物：
  描述：

  丙炔酸甲酯 、 5-chloro-3-(4-methoxyphenyl)-6-methyl-2H-1,4-oxazin-2-one 以 甲苯 为溶剂， 以88%的产率得到6-Chloro-2-(4-methoxy-phenyl)-5-methyl-nicotinic acid methyl ester
  参考文献：
  名称：

  Generation of 3-piperidine(methan)amines and cyclic 3-piperidine-methanamines as potential substance P antagonists

  摘要：

  A general method is described for the synthesis of 3-piperidine(methan)amines and their cyclic analogues. The 3,5-dichloro-2H-1,4-oxazin-2-ones 6 and 3-aryl substituted analogues are reacted with acetylenic dienophiles yielding pyridines. Further catalytic hydrogenation and functional group transformation (1) or substitution (2-3) with ring closure reactions (4) followed by hydrogenation provided the 2,3,5-cis substituted piperidines 1-3 and a cis substituted [3,4-c]pyrrolopiperidine 4. These compounds have recently raised great interest due to their Substance P antagonist profiles. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00791-6

文献信息

• Generation of 3-piperidine(methan)amines and cyclic 3-piperidine-methanamines as potential substance P antagonists
  作者：Nele Knoops、Geert Deroover、Zhang Jidong、Frans Compernolle、Georges J. Hoornaert

  DOI：10.1016/s0040-4020(97)00791-6

  日期：1997.9

  A general method is described for the synthesis of 3-piperidine(methan)amines and their cyclic analogues. The 3,5-dichloro-2H-1,4-oxazin-2-ones 6 and 3-aryl substituted analogues are reacted with acetylenic dienophiles yielding pyridines. Further catalytic hydrogenation and functional group transformation (1) or substitution (2-3) with ring closure reactions (4) followed by hydrogenation provided the 2,3,5-cis substituted piperidines 1-3 and a cis substituted [3,4-c]pyrrolopiperidine 4. These compounds have recently raised great interest due to their Substance P antagonist profiles. (C) 1997 Elsevier Science Ltd.