Methyl 2-oxo-6-(prop-2-ynylamino)benzo[h]chromene-4-carboxylate | 1338250-18-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: Methyl 2-oxo-6-(prop-2-ynylamino)benzo[h]chromene-4-carboxylate
• 英文别名: methyl 2-oxo-6-(prop-2-ynylamino)benzo[h]chromene-4-carboxylate
• CAS: 1338250-18-2
• 化学式: C₁₈H₁₃NO₄
• 分子量: 307.306
• InChiKey: VSWSSZFAPKADKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 2-oxo-6-(prop-2-ynylamino)benzo[h]chromene-4-carboxylate 在 三氟化硼乙醚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以42%的产率得到2H-benzo[h]pyrano[3,2-f]quinolin-2-one
  参考文献：
  名称：

  Synthesis of [5,6]-fused pyridocoumarins through aza-Claisen rearrangement of 6-propargylaminocoumarins

  摘要：

  [5,6]-Fused pyridocoumarins are prepared through aza-Claisen rearrangement and subsequent in situ cyclization of 6-propargylaminocoumarins under microwave irradiation in the presence of boron trifluoride diethyl etherate in N,N-dimethylformamide. During this process demethoxycarbonylation is observed in the corresponding 4-carbomethoxycoumarin derivatives. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.012
• 作为产物：
  描述：

  4-硝基-1-萘酚 在 甲酸 、 palladium 10% on activated carbon 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 120.5h， 生成 Methyl 2-oxo-6-(prop-2-ynylamino)benzo[h]chromene-4-carboxylate
  参考文献：
  名称：

  Synthesis of [5,6]-fused pyridocoumarins through aza-Claisen rearrangement of 6-propargylaminocoumarins

  摘要：

  [5,6]-Fused pyridocoumarins are prepared through aza-Claisen rearrangement and subsequent in situ cyclization of 6-propargylaminocoumarins under microwave irradiation in the presence of boron trifluoride diethyl etherate in N,N-dimethylformamide. During this process demethoxycarbonylation is observed in the corresponding 4-carbomethoxycoumarin derivatives. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.012

文献信息

• Synthesis of quinolines and fused pyridocoumarins from N-propargylanilines or propargylaminocoumarins by catalysis with gold nanoparticles supported on TiO2
  作者：Theodoros S. Symeonidis、Ioannis N. Lykakis、Konstantinos E. Litinas

  DOI：10.1016/j.tet.2013.04.026

  日期：2013.6

  [5,6]-Fused pyridocoumarins are prepared under mild conditions in excellent yields through the activation of the triple bond of 6-propargylaminocoumarins by gold nanoparticles supported on TiO2. The analogous reaction of N-propargylanilines with Au/TiO2 or Au/Al2O3 resulted in the formation of quinolines.

  [5,6]-吡啶并香豆素是在温和的条件下通过负载在TiO 2上的金纳米粒子活化6-炔丙基氨基香豆素的三键而以极好的收率制备的。N-炔丙基苯胺与Au / TiO 2或Au / Al 2 O 3的类似反应导致喹啉的形成。
• Synthesis of [5,6]-fused pyridocoumarins through aza-Claisen rearrangement of 6-propargylaminocoumarins
  作者：Theodoros S. Symeonidis、Michael G. Kallitsakis、Konstantinos E. Litinas

  DOI：10.1016/j.tetlet.2011.08.012

  日期：2011.10

  [5,6]-Fused pyridocoumarins are prepared through aza-Claisen rearrangement and subsequent in situ cyclization of 6-propargylaminocoumarins under microwave irradiation in the presence of boron trifluoride diethyl etherate in N,N-dimethylformamide. During this process demethoxycarbonylation is observed in the corresponding 4-carbomethoxycoumarin derivatives. (C) 2011 Elsevier Ltd. All rights reserved.