9-nitro-6H-chromeno[4,3-b]quinolin-11-ol

• 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: 9-nitro-6H-chromeno[4,3-b]quinolin-11-ol
• 化学式: C₁₆H₁₀N₂O₄
• 分子量: 294.266
• InChiKey: UGLFIOXHOCIUJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  88.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-chloro-2H-chromene-3-carbaldehyde 、 2-氨基-5-硝基苯酚 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以65%的产率得到9-nitro-6H-chromeno[4,3-b]quinolin-11-ol
  参考文献：
  名称：

  Revisiting the reaction of β-chloroacroleins with 2-aminophenol: a new observation

  摘要：

  The reaction of beta-chloroacrolein with 1 equiv of 2-aminophenol in DMF proceeds smoothly to afford 11-hydroxy derivative of chromeno-quinoline in good yield. This single pot method allows for a rapid access to a variety of chromenoquinolines or oxepinoquinolines depending on the nature of P-chloroacrolein used. The structures were established by spectroscopic data and further confirmed by X-ray diffraction analysis. A plausible mechanism for this reaction has been proposed. The reaction seemed to proceed via a chloroimine species, whose intermediacy has been established, followed by the construction of the fused quinoline ring. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.10.101

文献信息

• Revisiting the reaction of β-chloroacroleins with 2-aminophenol: a new observation
  作者：Rabin Bera、G. Dhananjaya、Shambu Nath Singh、B. Ramu、Sai Uday Kiran、P. Rajender Kumar、K. Mukkanti、Manojit Pal

  DOI：10.1016/j.tet.2007.10.101

  日期：2008.1

  The reaction of beta-chloroacrolein with 1 equiv of 2-aminophenol in DMF proceeds smoothly to afford 11-hydroxy derivative of chromeno-quinoline in good yield. This single pot method allows for a rapid access to a variety of chromenoquinolines or oxepinoquinolines depending on the nature of P-chloroacrolein used. The structures were established by spectroscopic data and further confirmed by X-ray diffraction analysis. A plausible mechanism for this reaction has been proposed. The reaction seemed to proceed via a chloroimine species, whose intermediacy has been established, followed by the construction of the fused quinoline ring. (c) 2007 Elsevier Ltd. All rights reserved.