3-ethoxycarbonyl-4-hydroxy-6-methylcoumarin

• 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: 3-ethoxycarbonyl-4-hydroxy-6-methylcoumarin
• 英文别名: ethyl 4-hydroxy-6-methyl-2-oxo-2H-chromene-3-carboxylate；Ethyl 4-hydroxy-6-methyl-2-oxochromene-3-carboxylate
• 化学式: C₁₃H₁₂O₅
• 分子量: 248.235
• InChiKey: HWHXPCHTRZMHRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙二胺 、 3-ethoxycarbonyl-4-hydroxy-6-methylcoumarin 以 甲苯 为溶剂， 反应 4.0h， 以65%的产率得到N-(2-amino-1-ethyl)-4-hydroxy-6-methyl-2-oxo-2H-chromene-3-carboxamide
  参考文献：
  名称：

  Synthesis and evaluation of the antioxidant and anti-inflammatory activity of novel coumarin-3-aminoamides and their alpha-lipoic acid adducts

  摘要：

  In the present work a series of novel coumarin-3-carboxamides and their hybrids with the alpha-lipoic acid were designed, synthesized and tested as potent antioxidant and anti-inflammatory agents. The new compounds were evaluated for their antioxidant activity, their activity to inhibit in vitro lipoxygenase and their in vivo anti-inflammatory activity. In general, the derivatives were generally found to present antioxidant and anti-inflammatory activities. Discussion is made based on the results for the structure-activity relationships in order to define the structural features required for activity. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.12.027
• 作为产物：
  描述：

  2-acetoxy-5-methylbenzoic acid 在 盐酸 、 sodium hydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 50.5h， 生成 3-ethoxycarbonyl-4-hydroxy-6-methylcoumarin
  参考文献：
  名称：

  功能化 γ-苯基-β-羟基丁烯酸酯的新型短步合成及其通过 N-羟基苯并三唑方法环化为 4-羟基香豆素

  摘要：

  报道了一种合成功能化3-取代4-羟基香豆素的新方法。C-酰化化合物衍生自官能化乙酰水杨酸的 N-羟基苯并三唑酯与多种活性亚甲基化合物的反应，并环化为标题化合物。合成很简单，化合物的产率从 39% 到 80% 不等。文献中首次通过核磁共振光谱对新制备的 C-酰化化合物的结构进行了深入研究。

  DOI：

  10.1055/s-2004-829132

文献信息

• A Rh(<scp>iii</scp>)-catalyzed cascade C–H functionalization/cyclization reaction of salicylaldehydes with diazomalonates for the synthesis of 4-hydroxycoumarin derivatives
  作者：Guo-Dong Xu、Zhi-Zhen Huang

  DOI：10.1039/c8nj04576c

  日期：——

  A cascade C–H functionalization/cyclization reaction of salicylaldehydes with α-diazomalonates has been developed for the synthesis of 4-hydroxycoumarin derivatives under the catalysis of rhodium(III) and in the presence of acetic acid. A plausible mechanism involving aldehydic C(sp2)–H activation by rhodium(III) and rhodium(III) catalyzed carbene insertion is also proposed.

  已经开发了水杨醛与α-二氮杂丙二酸酯的级联C–H功能化/环化反应，用于在铑（III）催化下和乙酸存在下合成4-羟基香豆素衍生物。还提出了一个可能的机理，该机理涉及通过铑（III）和铑（III）催化的卡宾插入来驱使醛C（sp 2）-H活化。
• Novel Short-Step Synthesis of Functionalized γ-Phenyl-β-hydroxybutenoates and their Cyclization to 4-Hydroxycoumarins via the <i>N</i>-Hydroxybenzotriazole Methodology
  作者：Olga Igglessi-Markopoulou、Giorgos Athanasellis、Georgia Melagraki、Haralambos Chatzidakis、Antreas Afantitis、Anastasia Detsi、John Markopoulos

  DOI：10.1055/s-2004-829132

  日期：——

  A novel method for the synthesis of functionalized 3- substituted 4-hydroxycoumarins is reported. C-Acylation com- pounds were derived from the reaction of the N-hydroxybenzotri- azole ester of the functionalized acetyl salicylic acids and a variety of active methylene compounds and cyclized to the title com- pounds. The synthesis is simple and the compounds are produced in yields varying from 39 to

  报道了一种合成功能化3-取代4-羟基香豆素的新方法。C-酰化化合物衍生自官能化乙酰水杨酸的 N-羟基苯并三唑酯与多种活性亚甲基化合物的反应，并环化为标题化合物。合成很简单，化合物的产率从 39% 到 80% 不等。文献中首次通过核磁共振光谱对新制备的 C-酰化化合物的结构进行了深入研究。
• Synthesis and evaluation of the antioxidant and anti-inflammatory activity of novel coumarin-3-aminoamides and their alpha-lipoic acid adducts
  作者：Georgia Melagraki、Antreas Afantitis、Olga Igglessi-Markopoulou、Anastasia Detsi、Maria Koufaki、Christos Kontogiorgis、Dimitra J. Hadjipavlou-Litina

  DOI：10.1016/j.ejmech.2008.12.027

  日期：2009.7

  In the present work a series of novel coumarin-3-carboxamides and their hybrids with the alpha-lipoic acid were designed, synthesized and tested as potent antioxidant and anti-inflammatory agents. The new compounds were evaluated for their antioxidant activity, their activity to inhibit in vitro lipoxygenase and their in vivo anti-inflammatory activity. In general, the derivatives were generally found to present antioxidant and anti-inflammatory activities. Discussion is made based on the results for the structure-activity relationships in order to define the structural features required for activity. (C) 2009 Elsevier Masson SAS. All rights reserved.