2,6-dichloro-3-[N-(2-methoxyphenyl)methyl]aminomethyl-5-phenylpyridine | 197235-35-1

• 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: 2,6-dichloro-3-[N-(2-methoxyphenyl)methyl]aminomethyl-5-phenylpyridine
• CAS: 197235-35-1
• 化学式: C₂₀H₁₈Cl₂N₂O
• 分子量: 373.282
• InChiKey: XCRJQVWPWNTHSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.35
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  34.15
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,6-dichloro-3-[N-(2-methoxyphenyl)methyl]aminomethyl-5-phenylpyridine 在 platinum(IV) oxide 、 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 溶剂黄146 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 48.0h， 以57%的产率得到[N-(2-methoxyphenyl)methyl]-5-phenyl-3-piperidinemethanamine dihydrochloride
  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：

  3,5-二氯-6-苯基-2H-1,4-恶嗪-2-酮 在 sodium hydroxide 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 2.5h， 生成 2,6-dichloro-3-[N-(2-methoxyphenyl)methyl]aminomethyl-5-phenylpyridine
  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.