methyl 2-oxo-7,8,9,10-tetrahydro-2H-benzo[h]chromene-4-carboxylate | 1204665-90-6

• 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-7,8,9,10-tetrahydro-2H-benzo[h]chromene-4-carboxylate
• 英文别名: Methyl 2-oxo-7,8,9,10-tetrahydrobenzo[h]chromene-4-carboxylate
• CAS: 1204665-90-6
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: USYGAJXUHNODQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 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：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-oxo-7,8,9,10-tetrahydro-2H-benzo[h]chromene-4-carboxylate 在 甲酸 、 硫酸 、 palladium 10% on activated carbon 、 potassium nitrate 、 三乙胺 作用下， 反应 24.83h， 生成 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
• 作为产物：
  描述：

  四氢萘酚 、 丁炔二酸二甲酯 在 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 48.17h， 以71%的产率得到methyl 2-oxo-7,8,9,10-tetrahydro-2H-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 and anti-inflammatory evaluation of novel angularly or linearly fused coumarins
  作者：Theodoros Symeonidis、Konstantina C. Fylaktakidou、Dimitra J. Hadjipavlou-Litina、Konstantinos E. Litinas

  DOI：10.1016/j.ejmech.2009.09.004

  日期：2009.12

  Angular [7,8]-fused coumarins were obtained from the reaction of [2,3]-fused phenols with DMAD and PPh3, while linear [6,7]-fused coumarins were formed from the analogous reaction of [3,4]-fused phenols with DMAD and PPh3. These compounds were tested in vitro for antioxidant activity and they found to present significant scavenging activity. In parallel, these new compounds were evaluated in vivo for anti-inflammatory activity and they found to inhibit the carrageenin-induced paw edema (34-65%). Although their interaction with the free stable radical DPPH was low, the methyl 2,2-dimethyl-8-oxo-3,8-dihydro-2H-furo[2,3-h]chromene-6-carboxylate was the most potent (65%) in the in vivo experiment. The later seems to be a potent soybean Lipoxygenase inhibitor and does not acquire gastrointestinal toxicity. (C) 2009 Elsevier Masson SAS. All rights reserved.
• 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.