3-vinylquinolin-2(1H)-one | 50779-76-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-vinylquinolin-2(1H)-one
• 英文别名: 3-Vinyl-2-quinolon；3-Vinyl-2-chinolon；3-vinylquinolone；2(1H)-Quinolinone, 3-ethenyl-；3-ethenyl-1H-quinolin-2-one
• CAS: 50779-76-5
• 化学式: C₁₁H₉NO
• 分子量: 171.199
• InChiKey: DXWDVHRXEIKSBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-vinylquinolin-2(1H)-one 以86%的产率得到
  参考文献：
  名称：

  SHANMUGAM P.; SOUNDAZARAJAN N.; KANAKARAJAN K., J. CHEM. SOC. PERKIN TRANS., 1977, PART 1, NO 18, 2024-2025

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(2-formylphenyl)but-2-ynamide 在 sodium acetate 、 溶剂黄146 、 三对苯甲基膦 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以85%的产率得到3-vinylquinolin-2(1H)-one
  参考文献：
  名称：

  膦介导的MBH型/ Umpolung加成多米诺序列：香豆素的不同结构。

  摘要：

  我们在这里报告了通过膦酸酯介导的特权反应性的合理整合，进行了膦介导的MBH型反应/蛋白γ加成的多米诺过程。只需通过操作亲核试剂，开发的方案即可轻松实现面向多样性的多种三取代香豆素的构建。

  DOI：

  10.1021/acs.orglett.9b04248

文献信息

• Palladium-Catalyzed Reductive Aminocarbonylation of <i>o</i>-Iodophenol-Derived Allyl Ethers with <i>o</i>-Nitrobenzaldehydes to 3-Alkenylquinolin-2(1<i>H</i>)-ones
  作者：Jian-Li Liu、Wei Wang、Xinxin Qi、Xiao-Feng Wu

  DOI：10.1021/acs.orglett.2c00648

  日期：2022.3.25

  An attractive palladium-catalyzed reductive aminocarbonylation reaction of allylic ethers has been explored for the synthesis of 3-alkenylquinolin-2(1H)-one derivatives. With Mo(CO)6 as both CO surrogate and reductant, a variety of 3-alkenylquinolin-2(1H)-ones were obtained in good to excellent yields from o-iodophenol-derived allyl ethers with o-nitrobenzaldehydes as the nitrogen sources. This reaction

  已经探索了一种有吸引力的钯催化的烯丙基醚的还原氨基羰基化反应，用于合成 3-alkenylquinolin-2(1 H )-one 衍生物。以Mo(CO) 6作为CO 替代物和还原剂，以邻硝基苯甲醛为氮源，由邻碘苯酚衍生的烯丙基醚以良好至优异的收率获得了多种3-alkenylquinolin-2(1 H )-one . 该反应通过级联途径进行，不依赖于以前的烯丙基羰基化反应所需的高压 CO 气体。该策略为构建 3-alkenylquinolin-2(1 H )-ones 提供了新途径。
• Hydrogen-Bond-Mediated Enantio- and Regioselectivity in a Ru-Catalyzed Epoxidation Reaction
  作者：Philipp Fackler、Carola Berthold、Felix Voss、Thorsten Bach

  DOI：10.1021/ja107601k

  日期：2010.11.17

  A chiral epoxidation catalyst based on a tricyclic octahydro-1H-4,7-methanoisoindol-1-one scaffold, in which a hydrogen bonding site and the catalytically active ruthenium center are spatially separated, was synthesized. It was shown that epoxidation reactions in such a supramolecular catalyst occur with high enantio- and regioselectivity because the hydrogen bonds expose the substrate to the ruthenium

  合成了一种基于三环八氢-1H-4,7-methanoisoindol-1-one 支架的手性环氧化催化剂，其中氢键位点和催化活性钌中心在空间上分开。结果表明，这种超分子催化剂中的环氧化反应以高对映选择性和区域选择性发生，因为氢键将底物暴露于具有明显构象偏好的钌卟啉络合物。3-乙烯基喹诺酮的环氧化以高达 95% 的 ee（71% 产率）进行。
• Enantio- and Regioselective Epoxidation of Olefinic Double Bonds in Quinolones, Pyridones, and Amides Catalyzed by a Ruthenium Porphyrin Catalyst with a Hydrogen Bonding Site
  作者：Philipp Fackler、Stefan M. Huber、Thorsten Bach

  DOI：10.1021/ja305890c

  日期：2012.8.1

  An array of differently substituted 3-alkenylquinolones was synthesized, and the enantio- and regioselectivity of their Ru-catalyzed epoxidation were studied. A precursor ruthenium(II) complex with a chiral tricyclic gamma-lactam skeleton (octahydro-1H-4,7-methanoisoindol-1-one) was available by Sonogashira cross-coupling with a monobromo-substituted ruthenium(II) porphyrin. Enantioselective epoxidation reactions (60-83% yield, 85-98% ee) were achieved with this catalyst, and it was shown that the enantioselectivity depends critically on the presence of a two-point hydrogen bond interaction between the gamma-lactam site of the catalyst and the delta-lactam (quinolone) site of the substrate. DFT calculations support the hypothesis that the reaction occurs via a hydrogen-bound transition state, in which the 3-alkenylquinolone adopts an s-trans conformation. The calculations further revealed that this transition state is preferred over a competing s-cis transition state because it exerts less strain in the rigid backbone and because the hydrogen bond interaction is more stable. The catalyst loading required for complete conversion was low (<0.2 mol %), and turnover numbers exceeding 4000 were recorded. It was shown that there is little, if any, inhibition of the catalytic process by other quinolones, which could potentially compete with the binding site. A mechanistic model for the catalytic reaction is presented. In accordance with this model 3-alkenylpyridones reacted with similar enantioselectivities as the respective quinolones. The epoxidation products were unstable, however, and the enantiomeric purity (77-87% ee) of the products could be established only after derivatization. Primary alkenoic acid amides also underwent the epoxidation but gave the respective products in lower enantioselectivities (70% and 45% ee), presumably because the enantioface differentiation is hampered by the increased flexibility of the substrates, which exhibit two or three rotatable single bonds between the binding site and the reactive olefinic double bond.
• RAMASAMY K.; KALYANASUNDARAM S. K.; SHANMUGAM P., SYNTHESIS, 1978, NO 7, 545-547
  作者：RAMASAMY K.、 KALYANASUNDARAM S. K.、 SHANMUGAM P.

  DOI：——

  日期：——
• HCV NS3 PROTEASE INHIBITORS
  申请人：Merck & Co., Inc.

  公开号：EP2083844A2

  公开（公告）日：2009-08-05