3-iodo-1-methylquinolin-4(1H)-one | 52166-26-4

• 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-iodo-1-methylquinolin-4(1H)-one
• 英文别名: 3-iodo-1-methylquinolin-4-one
• CAS: 52166-26-4
• 化学式: C₁₀H₈INO
• 分子量: 285.084
• InChiKey: VEUDHWIQUCKVSM-UHFFFAOYSA-N

物化性质

• 熔点：
  196-198 °C
• 沸点：
  303.1±42.0 °C(Predicted)
• 密度：
  1.85±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-iodo-1-methylquinolin-4(1H)-one 在 异丙基氯化镁 、 重水 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到3-deutero-1-methylquinolin-4(1H)-one
  参考文献：
  名称：

  Pd-Catalyzed Dehydrogenative Cross-Coupling of Polyfluoroarenes with Heteroatom-Substituted Enones

  摘要：

  The first example of intermolecular regioselective alpha-arylation of heteroatom-substituted enones with polyfluoroarenes via twofold C-H bond functionalization using a palladium catalyst is reported. This approach provides rapid access to a wide range of alpha-fluoroarylated enones of interest in life science.

  DOI：

  10.1021/ol300240k
• 作为产物：
  描述：

  4-羟基喹啉 在 碘 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 3-iodo-1-methylquinolin-4(1H)-one
  参考文献：
  名称：

  Synthesis, antibacterial evaluation, and docking studies of azaisoflavone analogues generated by palladium-catalyzed cross coupling

  摘要：

  Palladium-catalyzed, cross-coupling reaction of N-methyl-3-iodo-4-quinolone with boronic acids or N-methyliminodi-acetic acid boronates to obtain azaisoflavone derivatives was investigated through conventional Suzuki Miyuara coupling or by slow release strategy. It has been observed that a slow release approach was a highly successful. In addition, a series of novel azaisoflavones containing alkynyl group were synthesized via Sonogashira reaction. The antibacterial activities of the all synthesized compounds were screened against series of bacterial strains. Furthermore, a molecular docking study was carried out for the most active compounds using Leadit 2.1.8 docking software, and the results were in good agreement with the experimental data. The details of synthetic methods, spectroscopic data, and biological results are reported.[GRAPHICS]

  DOI：

  10.1007/s00706-018-2252-5

文献信息

• Synthesis of (E)-3-Styrylquinolin-4(1H)-ones in Water by Ohmic Heating: a Comparison with Other Methodologies
  作者：Joana Pinto、Vera L. M. Silva、Luis M. N. B. F. Santos、Artur M. S. Silva

  DOI：10.1002/ejoc.201600150

  日期：2016.6

  Ohmic heating offers a very efficient way to perform organic reactions in aqueous media. Potentially bioactive (E)-3-styrylquinolin-4(1H)-ones were synthesized by the Heck reaction of 3-iodo-1-methylquinolin-4(1H)-one with styrenes in water and with ohmic heating. Pd(OAc)2 was used as catalyst, and tetrabutylammonium bromide was used as phase-transfer catalyst in the presence of an inorganic base.

  欧姆加热提供了一种在水性介质中进行有机反应的非常有效的方法。具有潜在生物活性的 (E)-3-styrylquinolin-4(1H)-ones 是通过 3-iodo-1-methylquinolin-4(1H)-one 与苯乙烯在水中和欧姆加热的 Heck 反应合成的。Pd(OAc)2用作催化剂，四丁基溴化铵用作在无机碱存在下的相转移催化剂。与其他既定程序的比较突出了这种新方法的好处。
• Stereoselective Palladium-Catalyzed Alkenylation and Alkynylation of Thioglycosides
  作者：Etienne Brachet、Jean-Daniel Brion、Mouad Alami、Samir Messaoudi

  DOI：10.1002/adsc.201300419

  日期：2013.9.16

  An efficient and unprecedented palladium‐catalyzed S‐glycosylation reaction of a range of alkenyl and alkynyl halides by using thiosugars as nucleophile partners has been established. With palladium diacetate in combination with Xantphos as the catalytic system, a variety of β‐alkenylthioglycosides as well as β‐alkynylthioglycosides can be prepared in good to excellent yields. The efficiency of this

  通过使用硫糖作为亲核试剂的伙伴，已经建立了有效且前所未有的钯催化的一系列链烯基和炔基卤化物的S-糖基化反应。将二乙酸钯与Xantphos结合用作催化体系，可以制备各种β-烯基硫代糖苷以及β-炔基硫代糖苷，而且收率很高。叶片封闭的β-葡萄糖苷酶抑制剂的正式合成充分证明了该通用方案的有效性。
• Dual Role of Rh(III) Catalyst Enables Regioselective Halogenation of (Electron-Rich) Heterocycles
  作者：Nils Schröder、Fabian Lied、Frank Glorius

  DOI：10.1021/jacs.5b00283

  日期：2015.2.4

  The Rh(III)-catalyzed selective bromination and iodination of electron-rich heterocycles is reported. Kinetic investigations show that Rh plays a dual role in the bromination, catalyzing the directed halogenation and preventing the inherent halogenation of these substrates. As a result, this method gives highly selective access to valuable halogenated heterocycles with regiochemistry complementary

  报道了 Rh(III) 催化的富电子杂环的选择性溴化和碘化。动力学研究表明，Rh 在溴化中起着双重作用，催化定向卤化并防止这些底物的固有卤化。因此，该方法可以高度选择性地获取有价值的卤化杂环，其区域化学与使用未催化方法获得的那些互补，后者依赖于这些类别底物的固有反应性。可以应用呋喃、噻吩、苯并噻吩、吡唑、喹诺酮和色酮。
• A copper-mediated cross-coupling approach for the synthesis of 3-heteroaryl quinolone and related analogues
  作者：Sanghye Shin、Yechan Kim、Kiho Kim、Sungwoo Hong

  DOI：10.1039/c4ob00939h

  日期：——

  An efficient and practical method for the direct cross-coupling between quinolones and a range of azoles was developed via copper-mediated C–H functionalization. This synthetic strategy provides a convenient access to a variety of C3-heteroaryl quinolones, quinolinone, nalidixic acid, uracil, pyridone and chromone derivatives, which are prominent structural motifs in many biologically active compounds

  通过铜介导的C–H官能化，开发了一种有效且实用的方法，用于喹诺酮与一系列唑类之间的直接交叉偶联。这种合成策略可方便地获得各种C3-杂芳基喹诺酮，喹啉酮，萘啶酸，尿嘧啶，吡啶酮和色酮衍生物，它们是许多生物活性化合物中的突出结构基序。
• A General Copper Powder-Catalyzed Ullmann-Type Reaction of 3-Halo-4(1<i>H</i>)-quinolones With Various Nitrogen-Containing Nucleophiles
  作者：Davide Audisio、Samir Messaoudi、Jean-François Peyrat、Jean-Daniel Brion、Mouâd Alami

  DOI：10.1021/jo200680j

  日期：2011.6.17

  3-(N-Substituted) 4(1H)-quinolinones were synthesized using the copper-catalyzed Ullmann C–N bond forming strategy in moderate to quantitative yields. Starting from 3-halo-4(1H)-quinolones, various nucleophiles including amides, lactams, sulfonamides and NH-containing azoles have been used successfully. In all cases, the reactions take place rapidly in toluene and proceed by using copper powder as

  使用铜催化的Ullmann C–N键形成策略以中等至定量的产率合成了3-（N-取代的）4（1 H）-喹啉酮。从3-卤代-4（1 H）-喹诺酮类化合物开始，已成功使用了各种亲核试剂，包括酰胺，内酰胺，磺酰胺和含NH的唑。在所有情况下，反应都在甲苯中迅速进行，并通过使用铜粉作为催化剂，DMEDA作为配体和K 2 CO 3作为碱进行。此外，在我们的Cu / DMEDA催化剂体系下，其他相关杂环，例如3-溴喹啉-2（1 H）-ones，3-溴香豆素和3,5-二溴-2-吡啶酮显示出与各种亲核试剂的良好或非常高的反应性。 。