oxo-6H-[1,3]-dioxolo[4,5-g]chromene-8-carboxylic acid methyl ester | 1204665-84-8

• 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: oxo-6H-[1,3]-dioxolo[4,5-g]chromene-8-carboxylic acid methyl ester
• 英文别名: methyl 6-oxo-6H-[1,3]dioxolo[4,5-g]chromene-8-carboxylate；Methyl 6-oxo-[1,3]dioxolo[4,5-g]chromene-8-carboxylate
• CAS: 1204665-84-8
• 化学式: C₁₂H₈O₆
• 分子量: 248.192
• InChiKey: OQNHDXRFUWTPBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  oxo-6H-[1,3]-dioxolo[4,5-g]chromene-8-carboxylic acid methyl ester 、 溴 以76%的产率得到
  参考文献：
  名称：

  NAGANUMA, HIDEO;KAWAHARA, YUKINORI, J. CHROMATOGR., 478,(1989) N, C. 149-158

  摘要：

  DOI：
• 作为产物：
  描述：

  芝麻酚 、 丁炔二酸二甲酯 在 三苯基膦 、 β-环糊精 作用下， 以 水 为溶剂， 反应 8.0h， 以75%的产率得到oxo-6H-[1,3]-dioxolo[4,5-g]chromene-8-carboxylic acid methyl ester
  参考文献：
  名称：

  “β-环糊精纳米反应器”在水中原位生成稳定磷叶立德催化合成香豆素衍生物

  摘要：

  图形摘要 摘要 通过三苯基膦、炔酸酯和苯酚（1-萘酚、2-萘酚和苯并 [1,3] 二氧六环-5-醇）的三组分反应，方便地一锅法合成香豆素衍生物。据报道，存在催化量 (4.5 mol%) 的 β-环糊精作为纳米催化剂和纳米反应器。由于在这种“β-环糊精纳米反应器”绿色反应系统的存在下使用了水，因此这种方法很有趣。

  DOI：

  10.1080/10426507.2015.1073285

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.