3-(4-甲氧基苯基)-1H-吡啶-2-酮 | 143074-71-9

• 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: 3-(4-甲氧基苯基)-1H-吡啶-2-酮
• 英文名称: 3-(4-methoxyphenyl)-2-pyridone
• 英文别名: 2-Hydroxy-3-(4-methoxyphenyl)pyridine；3-(4-methoxyphenyl)-1H-pyridin-2-one
• CAS: 143074-71-9
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: FQJUXUNSPNHVGG-UHFFFAOYSA-N

物化性质

• 沸点：
  446.5±45.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 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：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-甲氧基苯基)-1H-吡啶-2-酮 在 sodium hydride 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 14.33h， 生成 1,2-dihydro-3-(p-methoxyphenyl)-1-<<5(4)-methyl-4(5)-imidazolyl>methyl>-2-oxopyridine
  参考文献：
  名称：

  Novel 5-HT3 antagonists. Isoquinolinones and 3-aryl-2-pyridones

  摘要：

  Synthesis and pharmacological evaluation of a series of 1,2-dihydro-1-[(5-methyl-1-imidazol-4-yl)methyl]-2-oxopyridine 5-HT3 antagonists are described. The key pharmacophoric elements were defined as a basic nitrogen, a group capable of hydrogen bonding interactions, and an aromatic moiety. 1,2-Dihydro-2-oxopyridine moiety could be a good linking group because of its nicely planar structure. The steric limitations of the aromatic moiety were investigated by X-ray analysis and computer analysis and shown to be optimal when the aromatic moiety was constrained within an arched planar system, which could be successfully replaced by 3-(2-thienyl)-2-oxopyridine function or 6-amino-7-chloro-1-isoquinolinone function without any loss of the activity. Among the synthesized compounds, 42 showed the most potent activity in the inhibition of Bezold-Jarisch reflex in rats. Compounds 44a and 64 were orally active in the protection against cisplatin-induced emesis in dogs or ferrets. Structure-activity relationships are discussed.

  DOI：

  10.1021/jm00096a001
• 作为产物：
  描述：

  rac-(4aS,5S,10S,10aR)-3-(4-methoxyphenyl)-4a,5,10,10a-tetrahydro-5,10-epoxybenzo[g]quinolin-2(1H)-one 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以99 %的产率得到3-(4-甲氧基苯基)-1H-吡啶-2-酮
  参考文献：
  名称：

  铑催化非对映选择性 C–H 活化/[4 + 2] α,β-不饱和酰胺与双环烯烃的环化

  摘要：

  在此，我们报告了在温和和绿色条件下铑催化的烯基酰胺与双环烯烃的C-H活化/[4 + 2]环化的罕见例子。本研究中铑催化剂的反应性与钴催化乙烯基酰胺和双环烯烃之间的 C-H 活化/[3 + 2] 成环反应中观察到的反应性不同。此外，该反应在室温下在EtOH中进行，还表现出优异的非对映选择性、良好的官能团耐受性和空气相容性。以良好至优异的产率获得了一系列新型桥环骨架。使用 1 或 0.75 mol% 铑催化剂进行放大实验，以优异的产率提供了所需的桥环骨架。

  DOI：

  10.1021/acs.orglett.3c03819

文献信息

• 2-Pyridonate Titanium Complexes for Chemoselectivity. Accessing Intramolecular Hydroaminoalkylation over Hydroamination
  作者：Eugene Chong、Laurel L. Schafer

  DOI：10.1021/ol402890m

  日期：2013.12.6

  Chemoselectivity of intramolecular hydroaminoalkylation over hydroamination has been achieved with a bis(3-phenyl-2-pyridonate) titanium complex. Primary aminoalkenes are selectively α-alkylated by C–H functionalization adjacent to nitrogen to access five- and six-membered cycloalkylamines with a good substrate-dependent diastereoselectivity of up to 19:1.

  用双（3-苯基-2-吡啶酮）钛配合物已经实现了分子内氢氨基烷基化对加氢胺化的化学选择性。伯氨基烯烃通过与氮相邻的CH官能团选择性地被α-烷基化，从而获得五元和六元环烷基胺，具有高达19：1的良好的底物依赖性非对映选择性。
• Novel 5-HT3 antagonists. Isoquinolinones and 3-aryl-2-pyridones
  作者：Toshiaki Matsui、Tsuneyuki Sugiura、Hisao Nakai、Sadahiko Iguchi、Satoshi Shigeoka、Hideo Takada、Yoshihiko Odagaki、Yuhki Nagao、Yasuyuki Ushio

  DOI：10.1021/jm00096a001

  日期：1992.9

  Synthesis and pharmacological evaluation of a series of 1,2-dihydro-1-[(5-methyl-1-imidazol-4-yl)methyl]-2-oxopyridine 5-HT3 antagonists are described. The key pharmacophoric elements were defined as a basic nitrogen, a group capable of hydrogen bonding interactions, and an aromatic moiety. 1,2-Dihydro-2-oxopyridine moiety could be a good linking group because of its nicely planar structure. The steric limitations of the aromatic moiety were investigated by X-ray analysis and computer analysis and shown to be optimal when the aromatic moiety was constrained within an arched planar system, which could be successfully replaced by 3-(2-thienyl)-2-oxopyridine function or 6-amino-7-chloro-1-isoquinolinone function without any loss of the activity. Among the synthesized compounds, 42 showed the most potent activity in the inhibition of Bezold-Jarisch reflex in rats. Compounds 44a and 64 were orally active in the protection against cisplatin-induced emesis in dogs or ferrets. Structure-activity relationships are discussed.
• Rhodium-Catalyzed Diastereoselective C–H Activation/[4 + 2] Annulation of α,β-Unsaturated Amides with Bicyclic Alkenes
  作者：Yan Wang、Sijia Shi、Wei Zhang、Yong Nian、Xiaowei Wu

  DOI：10.1021/acs.orglett.3c03819

  日期：2024.1.19

  rare example of rhodium-catalyzed C–H activation/[4 + 2] annulation of alkenyl amides with bicyclic alkenes under mild and green conditions. The reactivity of the rhodium catalyst in this study differed from that observed in cobalt-catalyzed C–H activation/[3 + 2] annulation between vinylic amides and bicyclic alkenes. In addition, the reaction was performed in EtOH at room temperature, which also displayed

  在此，我们报告了在温和和绿色条件下铑催化的烯基酰胺与双环烯烃的C-H活化/[4 + 2]环化的罕见例子。本研究中铑催化剂的反应性与钴催化乙烯基酰胺和双环烯烃之间的 C-H 活化/[3 + 2] 成环反应中观察到的反应性不同。此外，该反应在室温下在EtOH中进行，还表现出优异的非对映选择性、良好的官能团耐受性和空气相容性。以良好至优异的产率获得了一系列新型桥环骨架。使用 1 或 0.75 mol% 铑催化剂进行放大实验，以优异的产率提供了所需的桥环骨架。