1-甲基-4-苯基-2,3-二氢吡啶-6-酮 | 94515-22-7

• 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: 1-甲基-4-苯基-2,3-二氢吡啶-6-酮
• 英文名称: 1-methyl-4-phenyl-1,2,5,6-tetrahydropyridin-2-one
• 英文别名: 1-methyl-4-phenyl-5,6-dihydro-1H-pyridin-2-one；1-methyl-4-phenyl-5,6-dihydropyridin-2(1H)-one；1-methyl-2-oxo-4-phenyltetrahydropyridine；1-methyl-4-phenyl-5,6-dihydro-2-pyridone；2(1H)-Pyridinone, 5,6-dihydro-1-methyl-4-phenyl-；1-methyl-4-phenyl-2,3-dihydropyridin-6-one
• CAS: 94515-22-7
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: PYUKVRKFLFBZFL-UHFFFAOYSA-N

物化性质

• 沸点：
  364.8±32.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-甲基-4-苯基-2,3-二氢吡啶-6-酮 在 溴 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 1,4-二氧六环 为溶剂， 反应 1.17h， 以74%的产率得到3-bromo-1-methyl-4-phenyl-5,6-dihydro-1H-pyridin-2-one
  参考文献：
  名称：

  Remarkably Facile Hexatriene Electrocyclizations as a Route to Functionalized Cyclohexenones via Ring Expansion of Cyclobutenones

  摘要：

  This Communication describes a cascade reaction sequence that leads to highly functionalized cyclohexenones starting from reaction of cyclobutenones with alpha-lithio-alpha,beta-unsaturated sulfones and amides. The hexatriene-cyclohexadiene cyclization steps presumed to be involved in these transformations are among the most facile hexatriene electrocyclizations reported thus far.

  DOI：

  10.1021/ja0399066
• 作为产物：
  描述：

  1-甲基-4-苯基-1,2,3,6-四氢吡啶 在 potassium permanganate 作用下， 以 水 、 乙腈 为溶剂， 以65%的产率得到1-甲基-4-苯基-2,3-二氢吡啶-6-酮
  参考文献：
  名称：

  摘要：

  DOI：

  10.1023/a:1017570313032

文献信息

• Selective Reductions of 1-Methyl-4-phenyl-2-pyridone
  作者：Stéphane Mabic、Neal Castagnoli

  DOI：10.1021/jo951529v

  日期：1996.1.1

  We have explored the reactions of 1-methyl-4-phenyl-2-pyridone (5) with various reducing agents in an effort to develop synthetic approaches to specifically deuterium-labeled 1,4-disubstituted 1,2,3,6-tetrahydropyridine analogs needed for metabolic and enzyme mechanistic studies. Reactions with NaBH4 in CH3OH or THF, LiAl(O-t-Bu)(3)H in THF, and Al(i-Bu)(2)H(DIBALH) in THF resulted in quantitative recovery of starting material. On the other hand, treatment with BH3 in THF unexpectedly led to the formation of 4-phenylpyridine (7) in 98% yield. LiAIH(4) in THF or Et(2)O and Red-Al in THF gave varying amounts of the 3,6-dihydro-2-pyridone 8 and 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (1). In the presence of TiCl3, LiAlH4 in THF at 0 degrees C converted 5 to 1 in 97% yield. LiB(s-Bu)(3)H (L-Selectride) in THF gave exclusively the 1,4-reduction product 8. Base catalyzed isomerization of 8 provided the conjugated 5,6-dihydro-2-pyridone 4. The applications of these reactions with deuterated reagents provide insights into the reaction pathways and several avenues for the regioselective synthesis of the required deuterium-labeled compounds.
• ——
  作者：A. T. Soldatenkov、K. B. Polyanskii、S. A. Soldatova

  DOI：10.1023/a:1015612126244

  日期：——
• ——
  作者：A. T. Soldatenkov、T. P. Khristoforova、A. W. Temesgen、B. N. Anissimov、B. B Averkiev、L. N. Kuleshova、V. N. Khrustalev、M. Yu. Antipin

  DOI：10.1023/a:1011965312855

  日期：——
• [EN] USE OF LEPTIN FOR THE TREATMENT OR PREVENTION OF PARKINSON'S DISEASE<br/>[FR] UTILISATION DE LEPTINE POUR LE TRAITEMENT OU LA PRÉVENTION DE LA MALADIE DE PARKINSON
  申请人：UNIV TEXAS

  公开号：WO2008115880A2

  公开（公告）日：2008-09-25

  (EN) Disclosed are methods of treating or preventing Parkinson's disease or secondary parkinsonism in a subject, comprising administering to the subject a pharmaceutically effective amount of a leptin polypeptide, leptin transporter polypeptide, leptin receptor polypeptide, or a variant thereof, wherein administering the leptin polypeptide, leptin transporter polypeptide, leptin receptor polypeptide, or variant thereof results in treatment or prevention of Parkinson's disease or secondary parkinsonism in the subject.(FR) L'invention concerne des procédés de traitement ou de prévention de la maladie de Parkinson ou d'un parkinsonisme secondaire chez un sujet, comprenant l'administration au sujet d'une quantité pharmaceutiquement efficace d'un polypeptide de leptine, d'un polypeptide de transporteur de leptine, d'un polypeptide de récepteur de leptine ou d'une variante de ceux-ci, où l'administration du polypeptide de leptine, du polypeptide de transporteur de leptine, du polypeptide de récepteur de leptine ou de la variante de ceux-ci conduit au traitement ou à la prévention de la maladie de Parkinson ou du parkinsonisme secondaire chez le sujet.
• Remarkably Facile Hexatriene Electrocyclizations as a Route to Functionalized Cyclohexenones via Ring Expansion of Cyclobutenones
  作者：Nabi A. Magomedov、Piero L. Ruggiero、Yuchen Tang

  DOI：10.1021/ja0399066

  日期：2004.2.1

  This Communication describes a cascade reaction sequence that leads to highly functionalized cyclohexenones starting from reaction of cyclobutenones with alpha-lithio-alpha,beta-unsaturated sulfones and amides. The hexatriene-cyclohexadiene cyclization steps presumed to be involved in these transformations are among the most facile hexatriene electrocyclizations reported thus far.