1-(2-acetylphenyl)-1,2-dihydro-2-pyridone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-acetylphenyl)-1,2-dihydro-2-pyridone
• 英文别名: 1-(2-Acetylphenyl]-1H-pyridin-2-one；1-(2-acetylphenyl)pyridin-2-one
• 化学式: C₁₃H₁₁NO₂
• 分子量: 213.236
• InChiKey: ZGWXCQWOLQMBSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-acetylphenyl)-1,2-dihydro-2-pyridone 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 10.0h， 生成
  参考文献：
  名称：

  Light-Induced Enantiospecific 4π Ring Closure of Axially Chiral 2-Pyridones: Enthalpic and Entropic Effects Promoted by H-Bonding

  摘要：

  Nonbiaryl axially chiral 2-pyridones were synthesized and employed for light-induced electrocyclic 4 pi ring closure leading to bicyclo-beta-lactam photoproducts in solution. The enantioselectivity in the photoproducts varied from 22 to 95% depending on the reaction temperature and the ability of the axially chiral chromophore to form intramolecular and/or intermolecular H-bonds with the solvent. On the basis of the differential activation parameters, entropic control of the enantiospecificity was observed for 2-pyridones lacking the ability to form H-bonds. Conversely, enthalpy played a significant role for 2-pyridones having the ability to form H-bonds.

  DOI：

  10.1021/ja203087a
• 作为产物：
  描述：

  2-羟基吡啶 在 potassium carbonate 、 亚硝酸异戊酯 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 9.0h， 生成 1-(2-acetylphenyl)-1,2-dihydro-2-pyridone
  参考文献：
  名称：

  Unusual 1,4-Addition of 2-Pyridyl Carboxylates to Benzynes:  A Convenient Route to 1-(2-Acylphenyl)-2-pyridones

  摘要：

  DOI：

  10.1021/jo010162t

文献信息

• Unusual 1,4-Addition of 2-Pyridyl Carboxylates to Benzynes:  A Convenient Route to 1-(2-Acylphenyl)-2-pyridones
  作者：Dinesh Kumar Rayabarapu、Kanak Kanti Majumdar、Thota Sambaiah、Chien-Hong Cheng

  DOI：10.1021/jo010162t

  日期：2001.5.1
• Light-Induced Enantiospecific 4π Ring Closure of Axially Chiral 2-Pyridones: Enthalpic and Entropic Effects Promoted by H-Bonding
  作者：Elango Kumarasamy、Josepha L. Jesuraj、Joseph N. Omlid、Angel Ugrinov、Jayaraman Sivaguru

  DOI：10.1021/ja203087a

  日期：2011.11.2

  Nonbiaryl axially chiral 2-pyridones were synthesized and employed for light-induced electrocyclic 4 pi ring closure leading to bicyclo-beta-lactam photoproducts in solution. The enantioselectivity in the photoproducts varied from 22 to 95% depending on the reaction temperature and the ability of the axially chiral chromophore to form intramolecular and/or intermolecular H-bonds with the solvent. On the basis of the differential activation parameters, entropic control of the enantiospecificity was observed for 2-pyridones lacking the ability to form H-bonds. Conversely, enthalpy played a significant role for 2-pyridones having the ability to form H-bonds.