6,7-diethoxy-2H-chromen-2-one | 66384-56-3

• 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: 6,7-diethoxy-2H-chromen-2-one
• 英文别名: 6,7-diethoxy-coumarin；6,7-Diaethoxy-cumarin；6,7-bis(Ethyloxy)coumarin；6,7-diethoxychromen-2-one
• CAS: 66384-56-3
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: DGPDRQGWVNICCZ-UHFFFAOYSA-N

物化性质

• 沸点：
  389.5±42.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6,7-二羟基香豆素 、 碘乙烷 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.5h， 以54%的产率得到6,7-diethoxy-2H-chromen-2-one
  参考文献：
  名称：

  Semisynthesis, ex vivo evaluation, and SAR studies of coumarin derivatives as potential antiasthmatic drugs

  摘要：

  Asthma is a chronic inflammatory disorder that causes contraction in the smooth muscle of the airway and blocking of airflow. Reversal the contractile process is a strategy for the search of new drugs that could be used for the treatment of asthma. This work reports the semisynthesis, ex vivo relaxing evaluation and SAR studies of a series of 18 coumarins. The results pointed that the ether derivatives 1-3, 7-9 and 13-15 showed the best activity (E-max = 100%), where compound 2 (42 mu M) was the most potent, being 4-times more active than theophylline (positive control). The ether homologation (methyl, ethyl and propyl) in position 7 or positions 6 and 7 of coumarins lead to relaxing effect, meanwhile formation of esters generated less active compounds than ethers. The SAR analysis showed that it is necessary the presence of two small ether groups and the methyl group at position 4 (site 3) encourage biological activity through soft hydrophobic changes in the molecule, without drastically affecting the cLogP. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.029

文献信息

• METHOD FOR PRODUCING POLYDIENES AND POLYDIENE COPOLYMERS WITH REDUCED COLD FLOW
  申请人：Bridgestone Corporation

  公开号：US20140187725A1

  公开（公告）日：2014-07-03

  A method for preparing a coupled polymer, the method comprising the steps of: (i) polymerizing monomer to form a reactive polymer, and (ii) reacting the reactive polymer with coumarin or a substituted coumarin compound.
• US9127092B2
  申请人：——

  公开号：US9127092B2

  公开（公告）日：2015-09-08
• Semisynthesis, ex vivo evaluation, and SAR studies of coumarin derivatives as potential antiasthmatic drugs
  作者：Amanda Sánchez-Recillas、Gabriel Navarrete-Vázquez、Sergio Hidalgo-Figueroa、María Yolanda Rios、Maximiliano Ibarra-Barajas、Samuel Estrada-Soto

  DOI：10.1016/j.ejmech.2014.03.029

  日期：2014.4

  Asthma is a chronic inflammatory disorder that causes contraction in the smooth muscle of the airway and blocking of airflow. Reversal the contractile process is a strategy for the search of new drugs that could be used for the treatment of asthma. This work reports the semisynthesis, ex vivo relaxing evaluation and SAR studies of a series of 18 coumarins. The results pointed that the ether derivatives 1-3, 7-9 and 13-15 showed the best activity (E-max = 100%), where compound 2 (42 mu M) was the most potent, being 4-times more active than theophylline (positive control). The ether homologation (methyl, ethyl and propyl) in position 7 or positions 6 and 7 of coumarins lead to relaxing effect, meanwhile formation of esters generated less active compounds than ethers. The SAR analysis showed that it is necessary the presence of two small ether groups and the methyl group at position 4 (site 3) encourage biological activity through soft hydrophobic changes in the molecule, without drastically affecting the cLogP. (C) 2014 Elsevier Masson SAS. All rights reserved.