8-hydroxyquinoline-2-oxazoline | 220108-56-5

• 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: 8-hydroxyquinoline-2-oxazoline
• 英文别名: 2-[(4R)-4,5-Dihydro-4-phenyl-2-oxazolyl]-8-quinolinol；2-[(4R)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]quinolin-8-ol
• CAS: 220108-56-5
• 化学式: C₁₈H₁₄N₂O₂
• 分子量: 290.321
• InChiKey: PTZGPHAVQUTHJA-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  54.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 8-hydroxyquinoline-2-oxazoline 反应 1.0h， 以100%的产率得到[2-[(4R)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]quinolin-8-yl] acetate
  参考文献：
  名称：

  Acyl transfer of 8-acetoxy-2-oxazolinylquinoline assisted by hydrogen bonding formation

  摘要：

  A significant acceleration of acyl transfer has been achieved on 8-acetoxy-2-oxazolinylquinoline in the presence of benzylamine. Comparison of the aminolysis by the new acylating reagent with that of 8-acetoxyquinoline and 8-acetoxyquinoline-2-carbonitrile has been carried out. The results of these experiments suggest that the proximity of a supplementary basic atom to the ester group increases the participation effect of the basic site mainly by formation of a possible second hydrogen bond. The association constant of benzylamine into the basic cavity of 8-methoxy-2-oxazolinylquinoline (K-d = 80 M-1) has been measured by H-1 NMR titration experiments. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02329-2
• 作为产物：
  描述：

  D-苯甘氨醇 、 8-羟基喹啉-2-甲腈 在 copper dichloride 作用下， 100.0 ℃ 、999.91 Pa 条件下， 以55%的产率得到8-hydroxyquinoline-2-oxazoline
  参考文献：
  名称：

  Palladium-catalyzed allylic alkylation using pyridino-oxazolines and quinolino-oxazolines as ligands—influence of steric factors

  摘要：

  Four new chiral pyridino- and quinolino-oxazolines were subjected to the palladium-catalyzed alkylation of 1,3-diphenyl-2-propenyl acetate. The enantioselectivity varied (82-88% ee) with the steric properties of the ligands. The results are discussed in connection with results previously obtained using analogous ligands. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00346-2

文献信息

• Chiral ditopic receptors. Application to palladium-catalyzed allylic alkylation
  作者：Jean Bourguignon、Ulf Bremberg、Georges Dupas、Kristina Hallman、Lars Hagberg、Laurent Hortala、Vincent Levacher、Serghey Lutsenko、Emmanuel Macedo、Christina Moberg、Guy Quéguiner、Fredrik Rahm

  DOI：10.1016/j.tet.2003.10.005

  日期：2003.11

  Chiral pyridinooxazoline, quinolinooxazoline, bis(oxazolino)pyridine (pybox), and bisoxazoline (box) derivatives containing crown ether residues were prepared. Some of the ligands were assessed in substrate binding studies and in palladium catalyzed allylic alkylations. (C) 2003 Elsevier Ltd. All rights reserved.