1-ethyl-4-(γ-pyridyl)-1,2,5,6-tetrahydropyridine | 202980-39-0

• 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: 1-ethyl-4-(γ-pyridyl)-1,2,5,6-tetrahydropyridine
• 英文别名: 4-(1-ethyl-3,6-dihydro-2H-pyridin-4-yl)pyridine
• CAS: 202980-39-0
• 化学式: C₁₂H₁₆N₂
• 分子量: 188.272
• InChiKey: OCVCWEZOTQKQIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-ethyl-4-(γ-pyridyl)-1,2,5,6-tetrahydropyridine 在 potassium permanganate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.5h， 以81.4%的产率得到3,4-dihydroxy-1-ethyl-2-oxo-4-(γ-pyridyl)piperidine
  参考文献：
  名称：

  Oxidative reactions of azines

  摘要：

  Oxidative coupling of 1-alkyl(benzyl)-4-(gamma-Pyridyl)-1,2,5,6-tetrahydropyridines with acetone in the presence of KMnO4 follows two pathways and yields both 1-R-2-(acetylmethylene)tetrahydropyridines and 1-R-3,4-dihydroxypiperidin-2-ones. When acetonitrile is used instead of acetone, the reaction under similar conditions occurs as selective ketodihydroxylation of the starting piperideines yielding 1-R-3,4-dihydroxy-4(gamma-Pyridyl)piperidin-2-ones . The molecular and crystal structures of one of these products (R = Et) was studied by X-ray diffraction analysis.

  DOI：

  10.1007/bf02503786
• 作为产物：
  描述：

  1-ethyl-4-(4-pyridyl)pyridinium iodide 在 sodium tetrahydroborate 、 sodium carbonate 作用下， 以82.6%的产率得到1-ethyl-4-(γ-pyridyl)-1,2,5,6-tetrahydropyridine
  参考文献：
  名称：

  Oxidative reactions of azines

  摘要：

  Oxidative coupling of 1-alkyl(benzyl)-4-(gamma-Pyridyl)-1,2,5,6-tetrahydropyridines with acetone in the presence of KMnO4 follows two pathways and yields both 1-R-2-(acetylmethylene)tetrahydropyridines and 1-R-3,4-dihydroxypiperidin-2-ones. When acetonitrile is used instead of acetone, the reaction under similar conditions occurs as selective ketodihydroxylation of the starting piperideines yielding 1-R-3,4-dihydroxy-4(gamma-Pyridyl)piperidin-2-ones . The molecular and crystal structures of one of these products (R = Et) was studied by X-ray diffraction analysis.

  DOI：

  10.1007/bf02503786

文献信息

• Chemical model studies on the monoamine oxidase-B catalyzed oxidation of 4-substituted 1-cyclopropyl-1,2,3,6-tetrahydropyridines
  作者：Christelle Franot、Stéphane Mabic、Neal Castagnol Jr

  DOI：10.1016/s0968-0896(97)10033-5

  日期：1998.3

  dihydropyridinium products. Although the test compounds also were oxidized rapidly under SET conditions, no evidence for dihydropyridinium product formation was observed. The products that were identified most likely were formed after cyclopropyl ring opening of the initially formed cyclopropylaminyl radical cation. The results are discussed in terms of the mechanism of MAO-B catalysis.

  黄酮酶单胺氧化酶B（MAO-B）提出了两种催化途径-一种基于氮孤对的初始单电子转移（SET）步骤，另一种基于初始α-碳氢原子转移（ HAT）步骤。SET途径与各种环丙胺的基于机理的失活性质一致。MAO-B催化某些1-环丙基-4-取代的1,2,3,6-四氢吡啶有效氧化为相应的二氢吡啶鎓代谢物的观察结果表明，这些环状叔烯丙基胺的催化途径可能不会通过推定的进行SET产生了氨基自由基阳离子。本文描述了在模拟SET和HAT途径的反应条件下检测的一系列N-环丙基四氢吡啶的化学结局。在HAT反应条件下，所有测试化合物均迅速转化为其二氢吡啶鎓产物。尽管测试化合物在SET条件下也被快速氧化，但未观察到二氢吡啶鎓产物形成的证据。最可能被鉴定出的产物是在最初形成的环丙基胺基自由基阳离子的环丙基开环后形成的。就MAO-B催化的机理讨论了结果。没有观察到形成二氢吡啶鎓产物的证据。最可能被鉴定出的产物是在最初形成的环
• Oxidative reactions of azines
  作者：A. T. Soldatenkov、I. A. Bekro、S. A. Soldatova、E. Glover、A. Temesgen、L. N. Kuleshova、V. N. Khrustalev、N. D. Sergeeva

  DOI：10.1007/bf02503786

  日期：1997.11

  Oxidative coupling of 1-alkyl(benzyl)-4-(gamma-Pyridyl)-1,2,5,6-tetrahydropyridines with acetone in the presence of KMnO4 follows two pathways and yields both 1-R-2-(acetylmethylene)tetrahydropyridines and 1-R-3,4-dihydroxypiperidin-2-ones. When acetonitrile is used instead of acetone, the reaction under similar conditions occurs as selective ketodihydroxylation of the starting piperideines yielding 1-R-3,4-dihydroxy-4(gamma-Pyridyl)piperidin-2-ones . The molecular and crystal structures of one of these products (R = Et) was studied by X-ray diffraction analysis.