(2-溴-5-甲氧基苯基)(2-氯吡啶-3-基)甲酮 | 1438251-56-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (2-溴-5-甲氧基苯基)(2-氯吡啶-3-基)甲酮
• 英文名称: 2-chlorophenyl 2-chloro-3-pyridyl ketone
• 英文别名: (2-bromo-5-methoxyphenyl)(2-chloropyridin-3-yl)methanone；2-chloro-3-(2-chlorobenzoyl)pyridine；(2-chlorophenyl)(2-chloropyridin-3-yl)methanone；(2-Chlorophenyl)(2-chloro-3-pyridinyl)methanone；(2-chlorophenyl)-(2-chloropyridin-3-yl)methanone
• CAS: 1438251-56-9
• 化学式: C₁₂H₇Cl₂NO
• 分子量: 252.1
• InChiKey: JSRGHVVBWJTRTL-UHFFFAOYSA-N

物化性质

• 沸点：
  390.9±27.0 °C(Predicted)
• 密度：
  1.365±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• 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：

  (2-溴-5-甲氧基苯基)(2-氯吡啶-3-基)甲酮 在 sodiumsulfide nonahydrate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以88%的产率得到5H-thiochromeno[2,3-b]pyridin-5-one
  参考文献：
  名称：

  A Convenient Synthesis of 9H-Thioxanthen-9-ones and Their Aza-Analogues

  摘要：

  An efficient method for the preparation of 9H-thioxanthen-9-ones and their three aza-analogues has been developed. The reaction of (2-fluorophenyl)(2-halophenyl)methanones, derived from 1-bromo-2-fluorobenzenes and 2-halobenzaldehydes by an easy two-step sequence, with Na2S center dot 9H(2)O in DMF at 60 degrees C gives 9H-thioxanthen-9-ones. This procedure can be applied to the synthesis of 5H-[1]benzothiopyrano[2,3-b] (or [2,3-c])pyridin-5-ones or 10H-[1]benzothiopyrano[3,2-c]pyridin-10-ones starting from 2-, 3- or 4-chloropyridines, respectively.

  DOI：

  10.3987/com-13-12855
• 作为产物：
  描述：

  2-氯苯甲醛 在 pyridinium chlorochromate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (2-溴-5-甲氧基苯基)(2-氯吡啶-3-基)甲酮
  参考文献：
  名称：

  A Convenient Synthesis of 9H-Thioxanthen-9-ones and Their Aza-Analogues

  摘要：

  An efficient method for the preparation of 9H-thioxanthen-9-ones and their three aza-analogues has been developed. The reaction of (2-fluorophenyl)(2-halophenyl)methanones, derived from 1-bromo-2-fluorobenzenes and 2-halobenzaldehydes by an easy two-step sequence, with Na2S center dot 9H(2)O in DMF at 60 degrees C gives 9H-thioxanthen-9-ones. This procedure can be applied to the synthesis of 5H-[1]benzothiopyrano[2,3-b] (or [2,3-c])pyridin-5-ones or 10H-[1]benzothiopyrano[3,2-c]pyridin-10-ones starting from 2-, 3- or 4-chloropyridines, respectively.

  DOI：

  10.3987/com-13-12855

文献信息

• Functionalization of pyridyl ketones using deprotolithiation-in situ zincation
  作者：Madani Hedidi、William Erb、Frédéric Lassagne、Yury S. Halauko、Oleg A. Ivashkevich、Vadim E. Matulis、Thierry Roisnel、Ghenia Bentabed-Ababsa、Florence Mongin

  DOI：10.1039/c6ra11370b

  日期：——

  The metallation of aryl ketones was achieved by using LiTMP in the presence of ZnCl2·TMEDA, as evidenced by subsequent interception with iodine or by a palladium-catalysed cross-coupling reaction. One of the synthesized iodo ketones has been further elaborated to reach derivatives of biological interest.

  芳基酮的金属化是通过在ZnCl 2 ·TMEDA存在下使用LiTMP来实现的，随后通过碘的拦截或钯催化的交叉偶联反应证明了这一点。合成的碘代酮之一已被进一步精加工以达到具有生物学意义的衍生物。
• Identification of potent RORβ modulators: Scaffold variation
  作者：Christelle Doebelin、Rémi Patouret、Ruben D. Garcia-Ordonez、Mi Ra Chang、Venkatasubramanian Dharmarajan、Scott Novick、Anthony Ciesla、Sean Campbell、Laura A. Solt、Patrick R. Griffin、Theodore M. Kamenecka

  DOI：10.1016/j.bmcl.2018.08.017

  日期：2018.10

  We sought to develop ROR beta-selective probe molecules in order to investigate the function of the receptor in vitro and in vivo and its role in the pathophysiology of disease. To accomplish this, we modified a potent dual ROR beta/ROR gamma inverse agonist from the primary literature with the goal of improving selectivity for ROR beta vs ROR gamma. Truncation of the Western portion of the molecule ablated activity at ROR gamma and led to a potent series of ROR beta modulators. Continued exploration of this series investigated alternate replacement cores for the aminothiazole ring. Numerous suitable replacements were found during the course of our SAR investigations and are reported herein.
• Efficient two-step access to azafluorenones and related compounds
  作者：Nada Marquise、Philip J. Harford、Floris Chevallier、Thierry Roisnel、Andrew E.H. Wheatley、Philippe C. Gros、Florence Mongin

  DOI：10.1016/j.tetlet.2013.04.020

  日期：2013.6

  Crystals of a lithiocuprate prepared from copper(I) chloride and lithium 2,2,6,6-tetramethylpiperidide (2 equiv) were isolated and analyzed by X-ray diffraction as (TMP)(2)Cu(Cl)Li-2 center dot THF. The observation of this species is consistent with its having a role in deprotocupration-aroylation. Phenyl pyridyl ketones, phenyl quinolyl ketones, and phenyl thienyl ketones were prepared in tetrahydrofuran using the lithiocuprate and aroyl chorides as electrophiles. Diaryl ketones bearing a chloro group at the 2 position (of a pyridyl or phenyl group) thus synthesized were next converted through palladium-catalyzed ring closure to polycycles of the 5H-indeno[1,2-b]pyridin-5-one, 11H-indeno[1,2-b]quinolin-11-one, 9H-indeno[2,1-c]pyridin-9-one, and 8H-indeno[2,1-b]thiophen-8-one families. (C) 2013 Elsevier Ltd. All rights reserved.
• Substituted azafluorenones: access from dihalogeno diaryl ketones by palladium-catalyzed auto-tandem processes and evaluation of their antibacterial, antifungal, antimalarial and antiproliferative activities
  作者：Nada Marquise、Floris Chevallier、Ekhlas Nassar、Michel Frédérich、Allison Ledoux、Yury S. Halauko、Oleg A. Ivashkevich、Vadim E. Matulis、Thierry Roisnel、Vincent Dorcet、Florence Mongin

  DOI：10.1016/j.tet.2015.12.050

  日期：2016.2

  Substituted azafluorenones were synthesized from dihalogeno diaryl ketones under palladium catalysis by combining, in auto -tandem processes, Suzuki coupling and intramolecular arylation reactions. Different dihalogenated diaryl ketones, prepared by sequential deprotocupration-aroylation, were identified as suitable substrates to this purpose. Conditions were identified to allow successful syntheses of several 6-/7-arylated 4-azafluorenones, 1 -substituted 4-azafluorenones, 2-phenyl-3-azafluorenone, and 4-phenyl-3-azafluorenone from 3-(bromobenzoyl)-2-chloropyridines, 3-benzoyl-4-bromo-2-chloropyridines, 4-benzoyl-2,5-dichloropyridine, and 4-benzoyl-2,3-dichloropyridine, respectively. Some of the synthesized compounds exhibit interesting biological properties. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis of azafluorenones and related compounds using deprotocupration–aroylation followed by intramolecular direct arylation
  作者：Nada Marquise、Philip J. Harford、Floris Chevallier、Thierry Roisnel、Vincent Dorcet、Anne-Laure Gagez、Sophie Sablé、Laurent Picot、Valérie Thiéry、Andrew E.H. Wheatley、Philippe C. Gros、Florence Mongin

  DOI：10.1016/j.tet.2013.09.030

  日期：2013.11

  The efficiency of the deprotocupration-aroylation of 2-chloropyridine using lithiocuprates prepared from CuX (X=Cl, Br) and LiTMP (TMP=2,2,6,6-tetramethylpiperidido, 2 equiv) was investigated. CuCl was identified as a more suitable copper source than CuBr for this purpose. Different diaryl ketones bearing a halogen at the 2 position of one of the aryl groups were synthesized in this way from azines and thiophenes. These were then involved in palladium-catalyzed ring closure: substrates underwent expected CH-activation-type arylation to afford fluorenone-type compounds, and were also subjected to cyclization reactions leading to xanthones, notably in the presence of oxygen-containing substituents or reagents. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.