1-(3-oxobutyl)pyridin-2(1H)-one | 68634-50-4

• 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
• 英文名称: 1-(3-oxobutyl)pyridin-2(1H)-one
• 英文别名: 1-(3-oxo-butyl)-1H-pyridin-2-one；1-(2-Acetylethyl)-2-pyridon；1-(3-oxobutyl)pyridin-2-one
• CAS: 68634-50-4
• 化学式: C₉H₁₁NO₂
• 分子量: 165.192
• InChiKey: PJLWHDSYJAFZSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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-(3-oxobutyl)pyridin-2(1H)-one 在 bis(1,5-cyclooctadiene)nickel (0) 、 正丁基锂 、 7,9-bis(2,6-bis((R)-1-(3,5-dimethylphenyl)ethyl)-4-methylphenyl)-7H-acenaphtho[1,2-d]imidazol-8-ylidene 、 甲铝双(2,6-二叔丁基-4-苯甲醚) 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 25.0h， 生成 (1R,2R)-1,2-dimethyl-3,4-dihydro-1H-quinolizin-6(2H)-one 、 1,2-dimethyl-3,4-dihydro-1H-quinolizin-6(2H)-one
  参考文献：
  名称：

  Nickel-Catalyzed Enantioselective Pyridone C–H Functionalizations Enabled by a Bulky N-Heterocyclic Carbene Ligand

  摘要：

  Annulated pyridones are an important scaffold found in many biologically active compounds. A Ni(0)-catalyzed C-H functionalization of 2- and 4-pyridones is disclosed, providing access to annulated pyridones via enantioselective intramolecular olefin hydroarylation. Key to the success of the transformation was the development of a sterically hindered and tunable N-heterocyclic carbene ligand resembling a chiral version of IPr. This ligand allows for mild reaction temperatures, and leads to the annulated pyridones in excellent yields and enantioselectivities.

  DOI：

  10.1021/jacs.8b01181
• 作为产物：
  描述：

  2-羟基吡啶 、 β-氯代丁酮 在 potassium fluoride 、 苄基三乙基氯化铵 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以85%的产率得到1-(3-oxobutyl)pyridin-2(1H)-one
  参考文献：
  名称：

  Singh, Paramjit; Deep, Kanval; Singh, Harjit, Journal of Chemical Research, Miniprint, 1984, # 3, p. 636 - 650

  摘要：

  DOI：

文献信息

• SINGH, PARAMJIT;DEEP, KANWAL;SINGH, HARJIT, J. CHEM. RES. MICROFICHE, 1984, N 3, 71
  作者：SINGH, PARAMJIT、DEEP, KANWAL、SINGH, HARJIT

  DOI：——

  日期：——
• SOMEKAWA KENICHI; MIYAZATO MASAYUKI; MASUMORI RYUICHI; KUMAMOTO SANETADA, NIXON KAGAKU KAJSI, NIRRON KAGAKU KAISNI, J. CHEM. SOS. JAR., CHEM. AND I+
  作者：SOMEKAWA KENICHI、 MIYAZATO MASAYUKI、 MASUMORI RYUICHI、 KUMAMOTO SANETADA

  DOI：——

  日期：——
• Singh, Paramjit; Deep, Kanval; Singh, Harjit, Journal of Chemical Research, Miniprint, 1984, # 3, p. 636 - 650
  作者：Singh, Paramjit、Deep, Kanval、Singh, Harjit

  DOI：——

  日期：——
• Nickel-Catalyzed Enantioselective Pyridone C–H Functionalizations Enabled by a Bulky <i>N-</i>Heterocyclic Carbene Ligand
  作者：Johannes Diesel、Anastasiia M. Finogenova、Nicolai Cramer

  DOI：10.1021/jacs.8b01181

  日期：2018.4.4

  Annulated pyridones are an important scaffold found in many biologically active compounds. A Ni(0)-catalyzed C-H functionalization of 2- and 4-pyridones is disclosed, providing access to annulated pyridones via enantioselective intramolecular olefin hydroarylation. Key to the success of the transformation was the development of a sterically hindered and tunable N-heterocyclic carbene ligand resembling a chiral version of IPr. This ligand allows for mild reaction temperatures, and leads to the annulated pyridones in excellent yields and enantioselectivities.