2-methoxy-5-methyl-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carbonitrile | 68085-38-1

• 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-methoxy-5-methyl-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carbonitrile
• 英文别名: 2-methoxy-5-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carbonitrile；6-methoxy-3-methyl-2-oxo-3,4-dihydro-1H-pyridine-5-carbonitrile
• CAS: 68085-38-1
• 化学式: C₈H₁₀N₂O₂
• 分子量: 166.18
• InChiKey: JAXHWTHZHBYBIH-UHFFFAOYSA-N

物化性质

• 熔点：
  129-131 °C(Solv: methanol (67-56-1); hexane (110-54-3); ethyl acetate (141-78-6))
• 沸点：
  420.5±45.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methoxy-5-methyl-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carbonitrile 在 盐酸 、 甲醇 、 硫酸 、 sodium 、 溶剂黄146 、 锌 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 55.0h， 生成 7-amino-8-cyano-3,4-dihydro-3-methyl-1,6-naphthyridin-2(1H)-one
  参考文献：
  名称：

  Victory, Pedro J.; Teixido, Jordi; Borrell, Jose I., Heterocycles, 1992, vol. 34, # 10, p. 1905 - 1916

  摘要：

  DOI：
• 作为产物：
  描述：

  甲基丙烯酸甲酯 、 丙二腈 以49%的产率得到
  参考文献：
  名称：

  VICTORY, P.;NOMEN, R.;GARRIGA, M.;TOMAS, X.;SABATE, L. G., AFINIDAD, 1984, 41, N 391, 241-243

  摘要：

  DOI：

文献信息

• C4–C5 fused pyrazol-3-amines: when the degree of unsaturation and electronic characteristics of the fused ring controls regioselectivity in Ullmann and acylation reactions
  作者：Elisabeth Bou-Petit、Arnau Plans、Nieves Rodríguez-Picazo、Antoni Torres-Coll、Cristina Puigjaner、Mercè Font-Bardia、Jordi Teixidó、Santiago Ramon y Cajal、Roger Estrada-Tejedor、José I. Borrell

  DOI：10.1039/d0ob00796j

  日期：——

  number of compounds with a wide range of biological activities and, in many cases, the heterocycle is C4–C5 fused to a second ring. Among the different reactions used for the decoration of the pyrazole ring, Ullmann and acylation have been widely applied. However, there is some confusion in the literature regarding the regioselectivity of such reactions (substitution at N1 or N2 of the pyrazole ring) and

  吡唑-3-胺是存在于许多具有广泛生物活性的化合物中的支架，在许多情况下，杂环是C4–C5与第二个环稠合。在用于装饰吡唑环的不同反应中，Ullmann和酰化已得到广泛应用。然而，关于此类反应的区域选择性（吡唑环的N1或N2取代）的文献存在混淆，并且迄今尚未建立预测规则。作为我们对3-氨基-吡唑并[3,4- b ]吡啶酮的研究13，我们研究了在不同的C4–C5稠合的吡唑-3-胺中此类反应的区域选择性。根据经验，Ullmann和酰化反应主要发生在最稳定的初始互变异构体（1H-或2H-吡唑）的吡唑环的NH和非质子化氮原子上。通过使用DFT计算进行预测。
• Victory, Pedro; Nomen, Rosa; Colomina, Octavio, Heterocycles, 1985, vol. 23, # 5, p. 1135 - 1141
  作者：Victory, Pedro、Nomen, Rosa、Colomina, Octavio、Garriga, Miquel、Crespo, Ana

  DOI：——

  日期：——
• Victory, Pedro; Busquets, Nuria; Borrell, Jose I., Heterocycles, 1995, vol. 41, # 10, p. 2173 - 2180
  作者：Victory, Pedro、Busquets, Nuria、Borrell, Jose I.、Teixido, Jordi、Alvaro, Carlos de、et al.

  DOI：——

  日期：——
• Victory, Pedro J.; Teixido, Jordi; Borrell, Jose I., Heterocycles, 1993, vol. 36, # 1, p. 1 - 6
  作者：Victory, Pedro J.、Teixido, Jordi、Borrell, Jose I.、Busquets, Nuria

  DOI：——

  日期：——
• Cyclization of 5-Cyano-6-cyanoimino-3,4-dihydropyridin-2(1H)-ones with Amines
  作者：José I. Borrell、Núria Mont、Francisco Carrión、Jordi Teixidó

  DOI：10.3987/com-09-11860

  日期：——

  The cyclization of 5-cyano-6-cyanoimino-3,4-dihydropyridin-2(1h)-ones with amines, leading to pyrido[2,3-d]pyrimidines, is studied. Four play all important role oil the direction of cyclization: (1) the planarity of the reaction area; (2) the cyclization proceeds by the nucleophilic attack of all amidine onto ail electrophilic group which call be either a cyano group or all alkylamidine; (3) the basicity of the amine plays all important role, the ionization Of the Substrate making more difficult the formation of the aforementioned amidine which is needed for the cyclization; and (4) the nucleophilic attack and the tautomerization of the cyclization product are processes which call occur practically Simultaneously, so that the electronic movement involved in the tautomerization process coincides with the one which happens In the nucleophilic attack, both processes promoting each other.