(7-chloroquinolin-4-yl)(phenyl)methanone | 169957-11-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (7-chloroquinolin-4-yl)(phenyl)methanone
• 英文别名: (7-Chloroquinolin-4-yl)-phenylmethanone
• CAS: 169957-11-3
• 化学式: C₁₆H₁₀ClNO
• 分子量: 267.714
• InChiKey: FCHBFQQIEMUQIF-UHFFFAOYSA-N

物化性质

• 熔点：
  104-105 °C
• 沸点：
  435.9±25.0 °C(Predicted)
• 密度：
  1.294±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (7-chloroquinolin-4-yl)(phenyl)methanone 在 RuCl₂[(R)-(DM-BINAP)][(R)-DAIPEN] 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 25.0 ℃ 、275.8 kPa 条件下， 反应 24.0h， 以77%的产率得到(S)-(7-chloroquinolin-4-yl)(phenyl)methanol
  参考文献：
  名称：

  使用混合锂镁试剂合成 7-氯喹啉衍生物

  摘要：

  我们已经在温和条件下通过 7-氯喹啉的氧化制备了功能化喹啉库，采用间歇和连续流动条件。制备涉及混合锂镁中间体的产生，这些中间体与不同的亲电试剂反应。混合锂锌试剂允许合成卤化和芳基化衍生物。一些合成的 4-甲醇喹啉显示出有趣的抗增殖特性，它们的羟基是合适的氨基生物电子等排体。我们还报告了光学活性衍生物的两步法。

  DOI：

  10.1021/acs.joc.1c01521
• 作为产物：
  描述：

  7-氯-4-甲氧基喹啉 在 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.58h， 生成 (7-chloroquinolin-4-yl)(phenyl)methanone
  参考文献：
  名称：

  WO2007/104696

  摘要：

  公开号：

文献信息

• Palladium-N-heterocyclic carbene an efficient catalytic system for the carbonylative cross-coupling of pyridine halides with boronic acids
  作者：Eddy Maerten、Mathieu Sauthier、André Mortreux、Yves Castanet

  DOI：10.1016/j.tet.2006.11.008

  日期：2007.1

  Carbonylative cross-coupling of different pyridyl halides with various boronic acids was studied using catalytic systems constituted of N-heterocyclic carbene type ligands and palladium. These systems easily obtained in situ from the corresponding imidazolium salt and palladium acetate appear more efficient toward bromopyridines than catalysts based on hindered and basic alkylphosphines such as tricyclohexylphosphine

  使用由N-杂环卡宾型配体和钯组成的催化体系，研究了不同的吡啶基卤化物与各种硼酸的羰基化交叉偶联。从相应的咪唑鎓盐和乙酸钯就地获得的这些体系，对溴代吡啶的作用似乎比基于受阻和碱性烷基膦（例如三环己基膦）的催化剂更有效。通过使用实际上不与基于膦的催化体系反应的氯或二氯吡啶和氯喹啉偶联，也证明了它们较高的效率。
• Direct Synthesis of Benzoylpyridines from Chloropyridines via a Palladium-Carbene Catalyzed Carbonylative Suzuki Cross-Coupling Reaction
  作者：Yves Castanet、Eddy Maerten、Fatima Hassouna、Samuel Couve-Bonnaire、André Mortreux、Jean-François Carpentier

  DOI：10.1055/s-2003-41472

  日期：——

  The use of N-heterocyclic carbene-type ligands with palladium catalysts allows the activation of chloropyridines and chloroquinoline towards carbonylative cross-coupling with phenylboronic acid for the synthesis of unsymmetrical biaryl ketones.

  N-杂环卡宾型配体与钯催化剂的使用允许氯吡啶和氯喹啉活化，以与苯基硼酸进行羰基化交叉偶联，以合成不对称的联芳基酮。
• Preparation of pyridinyl aryl methanol derivatives by enantioselective hydrogenation of ketones using chiral Ru(diphosphine)(diamine) complexes. Attribution of their absolute configuration by 1H NMR spectroscopy using Mosher's reagent
  作者：Eddy Maerten、Francine Agbossou-Niedercorn、Yves Castanet、André Mortreux

  DOI：10.1016/j.tet.2008.06.104

  日期：2008.9

  provide highly efficient catalysts for enantioselective hydrogenation of a series of pyridinyl aryl ketones. The hydrogenation proceeds under mild conditions providing chiral pyridinyl aryl methanol derivatives with consistently high yields and moderate to excellent enantioselectivities (up to 99% ee) according to the structure of the chiral diphosphine. NMR studies, based on Mosher's ester derivatisation

  钌-二胺-二膦配合物为一系列吡啶基芳基酮的对映选择性加氢提供了高效的催化剂。根据手性二膦的结构，氢化反应在温和的条件下进行，从而提供了始终如一的高收率和中等至极好的对映选择性（高达99％ee）的手性吡啶基芳基甲醇衍生物。基于Mosher酯衍生化的NMR研究可以确定在不对称氢化过程中获得的主要醇的构型。
• Benzoylquinoiline derivatives
  申请人：NIHON BAYER AGROCHEM K.K.

  公开号：EP0669320A2

  公开（公告）日：1995-08-30

  Novel benzoylquinoline derivatives of the formula wherein R1 represents halogen, C1 -4 alkyl, C1 -4 haloalkoxy or C1 -4 haloalkyl, p represents an integer of 0 or 1, R2 represents halogen, nitro, cyano, C1-4 alkyl, C1-4 alkoxy, C1-4 alkylthio, C1-4 haloalkyl, C1-4 haloalkoxy or phenyl, and when m represents 2, then R2 may also represent methylenedioxy, m represents an integer of 0, 1, 2, 3, 4 or 5, R3 represents C1 -4 alkyl or C1 -4 haloalkyl, and n represents an integer of 0 or 1, and acid addition salts and metal salt complexes thereof, processes for the preparation of the new compounds and their use as fungicides.

  化合物的结构式为 其中， R1代表卤素、C1-4烷基、C1-4卤代烷氧基或C1-4卤代烷基； p代表0或1； R2代表卤素、硝基、氰基、C1-4烷基、C1-4烷氧基、C1-4烷硫基、C1-4卤代烷基、C1-4卤代烷氧基或苯基，当m为2时，R2还可以代表亚甲二氧基； m代表0、1、2、3、4或5； R3代表C1-4烷基或C1-4卤代烷基； n代表0或1； 此外，还包括它们的酸盐和金属盐络合物，以及制备这些新化合物的方法和它们作为杀真菌剂的用途。
• Clotrimazole Scaffold as an Innovative Pharmacophore Towards Potent Antimalarial Agents: Design, Synthesis, and Biological and Structure–Activity Relationship Studies
  作者：Sandra Gemma、Giuseppe Campiani、Stefania Butini、Gagan Kukreja、Salvatore Sanna Coccone、Bhupendra P. Joshi、Marco Persico、Vito Nacci、Isabella Fiorini、Ettore Novellino、Ernesto Fattorusso、Orazio Taglialatela-Scafati、Luisa Savini、Donatella Taramelli、Nicoletta Basilico、Silvia Parapini、Giulia Morace、Vanessa Yardley、Simon Croft、Massimiliano Coletta、Stefano Marini、Caterina Fattorusso

  DOI：10.1021/jm701247k

  日期：2008.3.13

  We describe herein the design, synthesis, biological evaluation, and structure-activity relationship (SAR) studies of an innovative class of antimalarial agents based on a polyaromatic pharmacophore structurally related to clotrimazole and easy to synthesize by low-cost synthetic procedures. SAR studies delineated a number of structural features able to modulate the in vitro and in vivo antimalarial activity. A selected set of antimalarials was further biologically investigated and displayed low in vitro toxicity on a panel of human and murine cell lines. In vitro, the novel compounds proved to be selective for free heme, as demonstrated in the beta-hematin inhibitory activity assay, and did not show inhibitory activity against 14-alpha-lanosterol demethylase (a fungal P450 cytochrome). Compounds 2, 4e, and 4n exhibited in vivo activity against P. chabaudi after oral administration and thus represent promising antimalarial agents for further preclinical development.