4-(4-fluorophenyl)-1-methylquinolin-2(1H)-one | 862191-01-3

• 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: 4-(4-fluorophenyl)-1-methylquinolin-2(1H)-one
• 英文别名: 4-(4-Fluorophenyl)-1-methylquinolin-2(1H)-one；4-(4-fluorophenyl)-1-methylquinolin-2-one
• CAS: 862191-01-3
• 化学式: C₁₆H₁₂FNO
• 分子量: 253.276
• InChiKey: JPVHUEGMZQQGLC-UHFFFAOYSA-N

物化性质

• 沸点：
  349.1±42.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对氟肉桂酸 在 草酰氯 、 2,4,5,6-四(9H-咔唑-9-基)异酞腈 、 三乙胺 、 N,N-二甲基甲酰胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 62.0h， 生成 4-(4-fluorophenyl)-1-methylquinolin-2(1H)-one
  参考文献：
  名称：

  Photoredox Cyclization of N-Arylacrylamides for Synthesis of Dihydroquinolinones

  摘要：

  DOI：

  10.1021/acs.orglett.1c04015

文献信息

• Efficient Route to 4-Substituted-2(5<i>H</i>)-furanones, 2(1<i>H</i>)-quinolones, and pyrones by Nickel-catalyzed Cross-coupling of Arenesulfonates with Organozinc Reagents
  作者：Jie Wu、Xiaoyu Sun、Liang Zhang

  DOI：10.1246/cl.2005.796

  日期：2005.6

  Nickel(II)-catalyzed cross-coupling reactions of 4-tosyl-2(1H)-quinolone, pyrone, and 2(5H)-furanone with various organozinc reagents provide an efficient and practical method for the high-yielding...

  镍 (II) 催化的 4-甲苯磺酰基-2(1H)-喹诺酮、吡喃酮和 2(5H)-呋喃酮与各种有机锌试剂的交叉偶联反应为高产...
• Palladium-catalyzed Suzuki–Miyaura couplings of potassium aryl trifluoroborates with 4-tosyloxycoumarins or 4-tosyloxyquinolin-2(1H)-one
  作者：Jie Wu、Liang Zhang、Hong-Guang Xia

  DOI：10.1016/j.tetlet.2006.01.020

  日期：2006.3

  Pd(PPh3)4 catalyzed Suzuki–Miyaura cross-coupling reactions of 4-tosyloxycoumarins or 4-tosyloxyquinolin-2(1H)-one with various potassium aryl trifluoroborates afforded the corresponding 4-substituted coumarins or 4-substituted quinolin-2(1H)-ones in good to excellent yield.

  Pd（PPh 3）4催化4-甲苯磺酰香豆素或4-甲苯磺酰喹啉-2（1 H）-之一与各种芳基三氟硼酸钾盐的Suzuki-Miyaura交叉偶联反应，得到相应的4-取代香豆素或4-取代喹啉-2（ 1 H）-良至优异的收率。
• RhCl(PPh3)3/DPPF: A Useful and Efficient Catalyst for Cross-Coupling Reactions of Activated Alkenyl Tosylates with Arylboronic Acids
  作者：Jie Wu、Liang Zhang、Ke Gao

  DOI：10.1002/ejoc.200600469

  日期：2006.12

  Suzuki–Miyaura cross-coupling of activated alkenyl tosylates is described. The results not only represent the first examples of the rhodium-catalyzed Suzuki–Miyaura coupling of activated alkenyl tosylates with arylboronic acids under mild conditions, but also provide an efficient route for the synthesis of some natural product-like compounds, such as furan-2(5H)-one, coumarin, pyrone, and quinolin-2(1H)-one

  描述了一种有用且有效的铑催化剂体系 - [RhCl(PPh3)3/DPPF] - 用于活化甲苯磺酸烯基酯的 Suzuki-Miyaura 交叉偶联。该结果不仅代表了在温和条件下活化的甲苯磺酸烯基与芳基硼酸在铑催化下 Suzuki-Miyaura 偶联的第一个例子，而且还为合成一些天然产物类化合物（如呋喃-2）提供了有效途径。 (5H)-one、香豆素、吡喃酮和喹啉-2(1H)-one 衍生物。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006）
• Rh(I)-catalyzed cross-coupling reactions of alkenyl tosylates with potassium aryltrifluoroborates
  作者：Jie Wu、Liang Zhang、Yong Luo

  DOI：10.1016/j.tetlet.2006.07.085

  日期：2006.9

  RhCl(PPh3)3/DPPF was successfully employed as an efficient catalyst in the Suzuki–Miyaura cross-coupling reactions of potassium aryltrifluoroborates with alkenyl tosylates, affording the corresponding products in good to excellent yields.

  RhCl（PPh 3）3 / DPPF已成功地用作芳基三氟硼酸钾与烯基甲苯磺酸盐的Suzuki-Miyaura交叉偶联反应的有效催化剂，以良好的收率获得了相应的产物。
• A novel and facile synthesis of 4-arylquinolin-2(1H)-ones under metal-free conditions
  作者：Bin Sun、Wen-Peng Mai、Liang-Ru Yang、Pu Mao、Jin-Wei Yuan、Yong-Mei Xiao

  DOI：10.1016/j.cclet.2015.05.008

  日期：2015.8

  A novel and facile synthesis of 4-arylquinolin-2(1H)-ones without metal catalysis has been developed. This reaction involved cyclization/elimination steps and was performed under metal-free conditions using inexpensive reagents such as NaI, selectfluor and KOH. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.