Methyl 6-amino-2-oxo-7,8,9,10-tetrahydrobenzo[h]chromene-4-carboxylate | 1338250-23-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: Methyl 6-amino-2-oxo-7,8,9,10-tetrahydrobenzo[h]chromene-4-carboxylate
• CAS: 1338250-23-9
• 化学式: C₁₅H₁₅NO₄
• 分子量: 273.288
• InChiKey: DXHOWXUJXMKTKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  78.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 6-amino-2-oxo-7,8,9,10-tetrahydrobenzo[h]chromene-4-carboxylate 在 三氟化硼乙醚 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 122.5h， 生成 9,10,11,12-tetrahydro-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：

  在 甲酸 、 palladium 10% on activated carbon 、 三乙胺 作用下， 反应 0.33h， 以78%的产率得到Methyl 6-amino-2-oxo-7,8,9,10-tetrahydrobenzo[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 methyl substituted [5,6]- and [7,8]-fused pyridocoumarins via the iodine-catalyzed reaction of aminocoumarins with n-butyl vinyl ether
  作者：Theodoros S. Symeonidis、Konstantinos E. Litinas

  DOI：10.1016/j.tetlet.2013.09.089

  日期：2013.11

  pyridocoumarins are prepared from the Povarov-type, three-component reactions of 6- or 7-aminocoumarins with n-butyl vinyl ether, catalyzed by iodine in refluxing acetonitrile, through the aza-Diels–Alder reaction of the initially formed N-iminoaminocoumarins with a second equivalent of the vinyl ether.

  2-甲基取代的[5,6]-或[7,8]-融合吡啶并香豆素是由碘催化的6-或7-氨基香豆素与正丁基乙烯基醚的Povarov型三组分反应制备的。乙腈通过最初形成的N-亚氨基氨基香豆素与第二当量的乙烯基醚的aza-Diels-Alder反应制得。
• Synthesis Through Three-Component Reactions Catalyzed by FeCl₃of Fused Pyridocoumarins as Inhibitors of Lipid Peroxidation
  作者：Theodoros S. Symeonidis、Dimitra J. Hadjipavlou-Litina、Konstantinos E. Litinas

  DOI：10.1002/jhet.1791

  日期：2014.5

  2,4‐Diphenyl substituted fused pyridocoumarins have been synthesized by one‐pot three‐component domino reactions of aminocoumarins, benzaldehyde, and phenylacetylene by using FeCl3 (10%) as catalyst under reflux or MW irradiation. The new compounds were tested as inhibitors of lipid peroxidation. The 7,9‐diphenyl‐2H‐pyrano[2,3‐g]quinolin‐2‐one presents interesting results and could serve as lead compound

  以氨基香豆素，苯甲醛和苯乙炔的一锅式三组分多米诺反应，以FeCl 3（10％）为催化剂，在回流或微波辐射下，合成了2,4-二苯基取代的稠合吡啶香豆素。测试了新化合物作为脂质过氧化抑制剂。7,9-二苯基-2- H-吡喃[2,3 - g ]喹啉-2-酮呈现有趣的结果，可以用作先导化合物。