methyl 6-chloro-2-(3,4-dimethoxyphenyl)-5-methyl-3-pyridinecarboxylate | 197235-08-8

• 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: methyl 6-chloro-2-(3,4-dimethoxyphenyl)-5-methyl-3-pyridinecarboxylate
• 英文别名: Methyl 6-chloro-2-(3,4-dimethoxyphenyl)-5-methylpyridine-3-carboxylate
• CAS: 197235-08-8
• 化学式: C₁₆H₁₆ClNO₄
• 分子量: 321.76
• InChiKey: GNXXCNGZQVTCMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 6-chloro-2-(3,4-dimethoxyphenyl)-5-methyl-3-pyridinecarboxylate 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 sodium periodate 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 氯仿 、 水 、 溶剂黄146 为溶剂， 20.0~100.0 ℃ 、101.33 kPa 条件下， 反应 21.0h， 生成 (1S,3R,11bR)-9,10-Dimethoxy-3-methyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline-1-carboxylic acid methyl ester
  参考文献：
  名称：

  通过2-芳基取代的吡啶的1,3-二取代的苯并[ a ]喹啉嗪骨架的通用立体有择合成

  摘要：

  从容易获得的3芳基化6取代的恶嗪酮2开始，描述了1,3-二取代的苯并[ a ]喹啉嗪6的立体有择合成。通过分子内芳族取代在骨架上用缩水甘油处理中间哌啶4并连续氧化裂解二醇，从而在α-氨基醛上修饰骨架。

  DOI：

  10.1016/s0040-4039(99)01943-7
• 作为产物：
  描述：

  丙炔酸甲酯 、 5-chloro-3-(3,4-dimethoxyphenyl)-6-methyl-2H-1,4-oxazin-2-one 以 甲苯 为溶剂， 以90%的产率得到methyl 6-chloro-2-(3,4-dimethoxyphenyl)-5-methyl-3-pyridinecarboxylate
  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.
• A versatile stereospecific synthesis of the 1,3-disubstituted benzo[a]quinolizidine framework via 2-aryl substituted pyridines
  作者：Erik Van der Eycken、Geert Deroover、Suzanne M. Toppet、Georges J. Hoornaert

  DOI：10.1016/s0040-4039(99)01943-7

  日期：1999.12

  The stereospecific synthesis of the 1,3-disubstituted benzo[a]quinolizidine 6 is described starting from the easily accessible 3-arylated-6-substituted oxazinone 2. The skeleton is elaborated via an intramolecular aromatic substitution on the α-amino aldehyde obtained by treatment of the intermediate piperidine 4 with glycidol and consecutive oxidative cleavage of the diol.

  从容易获得的3芳基化6取代的恶嗪酮2开始，描述了1,3-二取代的苯并[ a ]喹啉嗪6的立体有择合成。通过分子内芳族取代在骨架上用缩水甘油处理中间哌啶4并连续氧化裂解二醇，从而在α-氨基醛上修饰骨架。