2-chlorophenyl 2-methoxy-3-pyridyl ketone | 1438251-51-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-chlorophenyl 2-methoxy-3-pyridyl ketone
• 英文别名: (2-Chlorophenyl)-(2-methoxypyridin-3-yl)methanone
• CAS: 1438251-51-4
• 化学式: C₁₃H₁₀ClNO₂
• 分子量: 247.681
• InChiKey: QHWRZYMBHPJUQR-UHFFFAOYSA-N

物化性质

• 沸点：
  405.6±35.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chlorophenyl 2-methoxy-3-pyridyl ketone 在 四丙基氯化铵 、 palladium diacetate 、 potassium carbonate 、 tricyclohexylphosphine tetrafluoroborate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以48%的产率得到1-methoxy-9H-indeno[2,1-c]pyridin-9-one
  参考文献：
  名称：

  Synthesis of azafluorenones and related compounds using deprotocupration–aroylation followed by intramolecular direct arylation

  摘要：

  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.

  DOI：

  10.1016/j.tet.2013.09.030
• 作为产物：
  描述：

  2-甲氧基吡啶 、 邻氯苯甲酰氯 在 四甲基乙二胺 、 (TMP)2CuLi·LiCl 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以56%的产率得到2-chlorophenyl 2-methoxy-3-pyridyl ketone
  参考文献：
  名称：

  Efficient two-step access to azafluorenones and related compounds

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2013.04.020