1-methyl-4-(indazol-1-yl)-1,2,3,6-tetrahydropyridine | 229628-92-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: 1-methyl-4-(indazol-1-yl)-1,2,3,6-tetrahydropyridine
• 英文别名: 1-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)indazole
• CAS: 229628-92-6
• 化学式: C₁₃H₁₅N₃
• 分子量: 213.282
• InChiKey: HOVCSHAZPPGISS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  21.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methyl-4-(indazol-1-yl)-1,2,3,6-tetrahydropyridine 在 高氯酸 、 间氯过氧苯甲酸 、 三氟乙酸酐 作用下， 以 氯仿 为溶剂， 反应 1.5h， 生成 1-methyl-4-(1H-indazolyl)-2,3-dihydropyridinium perchlorate
  参考文献：
  名称：

  Studies on the Monoamine Oxidase-B-Catalyzed Biotransformation of 4-Azaaryl-1-methyl-1,2,3,6-tetrahydropyridine Derivatives

  摘要：

  The substrate properties of a series of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridinyl (MPTP) analogues in which the C-4 phenyl group has been replaced with various 4-azaaryl moieties have been examined in an effort to evaluate the contribution of electronic, polar, and steric parameters to the MAO-B-catalyzed oxidation of this type of cyclic tertiary allylamine to the corresponding dihydropyridinium metabolite. No significant correlation could be found nit-h the calculated energy of the C-H bond undergoing cleavage. A general trend, however, was observed between the magnitude of the log P value with the magnitude of k(cat)/K-m. The results indicate that the placement of a polar nitrogen atom in the space occupied by the phenyl group of MPTP leads to a dramatic decrease in substrate properties. Enhanced substrate properties, however, were observed when benzoazaarenes replaced the corresponding five-membered azaarenes. These results are consistent with our previously published molecular model of the active site of MAO-B.

  DOI：

  10.1021/jm9900319
• 作为产物：
  描述：

  4-chloro-1-methylpyridinium iodide 在 2,2,6,6-四甲基哌啶 、 sodium tetrahydroborate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 36.0h， 生成 1-methyl-4-(indazol-1-yl)-1,2,3,6-tetrahydropyridine
  参考文献：
  名称：

  1H-和2H-吲唑基衍生物的合成方法研究。

  摘要：

  据报道，旨在提供具有潜在生物学意义的1H-和2H-吲唑基衍生物的合成方法。特别强调了在不同条件下由吲唑与4-氯-1-甲基吡啶碘化物反应生成的吲唑基吡啶鎓产物的特性。在室温下在碱2,2,6,6-四甲基哌啶（TMP）的存在下，获得了由3份1H-异构体9到1份2H-异构体10组成的稳定混合物。在60℃下的相同反应仅得到1H-异构体9。在100℃下，在不存在TMP的情况下，仅形成2H-异构体10。发现10至9的异构化在60℃下定量进行，但仅在TMP存在下进行。

  DOI：

  10.1021/jo005786y

文献信息

• Studies on Synthetic Approaches to 1<i>H</i>- and 2<i>H</i>-Indazolyl Derivatives
  作者：Emre M. Isin、Milly de Jonge、Neal Castagnoli

  DOI：10.1021/jo005786y

  日期：2001.6.1

  2H-indazolyl derivatives of potential biological interest are reported. Special emphasis has been placed on the characterization of indazolylpyridinium products generated from reactions between indazole and 4-chloro-1-methylpyridinium iodide under various conditions. A stable mixture consisting of 3 parts of the 1H-isomer 9 to 1 part of the 2H-isomer 10 was obtained at room temperature in the presence

  据报道，旨在提供具有潜在生物学意义的1H-和2H-吲唑基衍生物的合成方法。特别强调了在不同条件下由吲唑与4-氯-1-甲基吡啶碘化物反应生成的吲唑基吡啶鎓产物的特性。在室温下在碱2,2,6,6-四甲基哌啶（TMP）的存在下，获得了由3份1H-异构体9到1份2H-异构体10组成的稳定混合物。在60℃下的相同反应仅得到1H-异构体9。在100℃下，在不存在TMP的情况下，仅形成2H-异构体10。发现10至9的异构化在60℃下定量进行，但仅在TMP存在下进行。
• Studies on the Monoamine Oxidase-B-Catalyzed Biotransformation of 4-Azaaryl-1-methyl-1,2,3,6-tetrahydropyridine Derivatives
  作者：Sandeep K. Nimkar、Stéphane Mabic、Andrea H. Anderson、Sonya L. Palmer、Thomas H. Graham、Milly de Jonge、Lisa Hazelwood、Sean J. Hislop、Neal Castagnoli

  DOI：10.1021/jm9900319

  日期：1999.5.1

  The substrate properties of a series of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridinyl (MPTP) analogues in which the C-4 phenyl group has been replaced with various 4-azaaryl moieties have been examined in an effort to evaluate the contribution of electronic, polar, and steric parameters to the MAO-B-catalyzed oxidation of this type of cyclic tertiary allylamine to the corresponding dihydropyridinium metabolite. No significant correlation could be found nit-h the calculated energy of the C-H bond undergoing cleavage. A general trend, however, was observed between the magnitude of the log P value with the magnitude of k(cat)/K-m. The results indicate that the placement of a polar nitrogen atom in the space occupied by the phenyl group of MPTP leads to a dramatic decrease in substrate properties. Enhanced substrate properties, however, were observed when benzoazaarenes replaced the corresponding five-membered azaarenes. These results are consistent with our previously published molecular model of the active site of MAO-B.