2-甲基-6-氧代-1,4,5,6-四氢-3-吡啶甲腈 | 27036-90-4

• 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
• 中文名称: 2-甲基-6-氧代-1,4,5,6-四氢-3-吡啶甲腈
• 英文名称: 6-methyl-1,2,3,4-tetrahydro-2-pyridinone-5-carbonitrile
• 英文别名: 5-Cyan-6-methyl-3,4-dihydro-2-pyridon；2-methyl-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carbonitrile；2-Methyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carbonitrile；6-methyl-2-oxo-3,4-dihydro-1H-pyridine-5-carbonitrile
• CAS: 27036-90-4
• 化学式: C₇H₈N₂O
• mdl: MFCD00974996
• 分子量: 136.153
• InChiKey: JMOQBKDWJOUOAP-UHFFFAOYSA-N

物化性质

• 熔点：
  222-224°C
• 沸点：
  347.9±42.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933399090

反应信息

• 作为产物：
  描述：

  (2R,3R)-2-Dimethylamino-2-methyl-6-methylsulfanyl-2,3,4,5-tetrahydro-pyridine-3-carbonitrile 在 水 作用下， 生成 2-甲基-6-氧代-1,4,5,6-四氢-3-吡啶甲腈
  参考文献：
  名称：

  在1,3位带有电子释放取代基的2-氮杂-1,3-二烯。用于构建吡啶和嘧啶衍生物的试剂

  摘要：

  通过N-亚硫基乙am碘化物的去质子化，由N-硫代酰基乙acet制备带有1和3-供体取代基的新的2-氮杂-1,3-二烯。2-氮杂-3-（二甲基氨基）-1-（甲硫基）-1-苯基丁二烯（3）被残留的前体盐作为异二烯基团原位捕获，得到嘧啶5。取代的2-氮杂-1-（二甲基氨基）-3-（甲硫基）类似物容易与各种缺电子的亲二烯体反应，生成吡啶或嘧啶衍生物。富马酸二甲酯和丙烯腈情况下的杂Diels-Alder反应的立体化学已通过所得四氢吡啶的X射线衍射分析确定，并对应于exo选择性。在乙炔二羧酸二甲酯和异硫氰酸苯酯的情况下，环加合物的数量和性质取决于C-4取代。由C-4未取代的氮杂丁二烯8获得的结果由涉及伯[4 + 2]加合物中二甲基氨基的1,3-迁移的烯丙基重排解释。

  DOI：

  10.1016/0040-4020(96)00546-7

文献信息

• “Conformationally restricted β-amino acid isosteres prepared through regioselectively controlled aza-annulation.”
  作者：K. Paulvannan、John R. Stille

  DOI：10.1016/s0040-4039(00)61389-8

  日期：1993.12

  A variety of electron withdrawing substituents were used to enhance the aza-annulation of enamines with acryloyl chloride, to direct the regioselectivity of alkene formation, and to facilitate hydrogenation of the unsaturated annulation product. The resulting δ-lactam products were β-amino acid analogs with structural features similar to those of established peptide isosteres.

  多种吸电子取代基用于增强烯胺与丙烯酰氯的氮杂-环氧化，以指导烯烃形成的区域选择性，并促进不饱和环化产物的氢化。所得的δ-内酰胺产物是β-氨基酸类似物，其结构特征与已建立的肽等排物相似。
• Heterocycle Formation through Aza-Annulation: Stereochemically Controlled Syntheses of (.+-.)-5-Epitashiromine and (.+-.)-Tashiromine
  作者：K. Paulvannan、John R. Stille

  DOI：10.1021/jo00086a009

  日期：1994.4

  N-alkylenamines, stabilized through conjugation with an electron-withdrawing group, undergo aza-annulation with acryloyl chloride to provide a convergent route for the construction of six-membered nitrogen heterocycles. In addition to enhancing the C-alkylation process of annulation relative to the competing N-acylation process, the electron withdrawing substituent controlled the regioselectivity of alkene formation in both the intermediate enamine and in the unsaturated lactam product. A variety of functional groups, which include -COMe, -COPh, -CO(2)R, -CONHPh, -CN, -P(O)(OEt)(2), and -SO(2)Ph, were used to determine the effect of the electron-withdrawing substituents upon both the annulation reaction with acryloyl chloride and the subsequent hydrogenation process. When the enamide annulation product was stabilized through conjugation with ester or amide substituents, catalytic hydrogenation of the ate-annulation product resulted in the formation of vicinal stereocenters with high cis selectivity. The utility of this methodology was demonstrated by application of the condensation/aza-annulation/hydrogenation sequence as the key for construction and stereochemical control of the indolizidine ring system of (+/-)-tashiromine.

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