4-羟基-2-氧代-2H-1-苯并吡喃-3-羧酸乙酯 | 1821-20-1

• 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
• 中文名称: 4-羟基-2-氧代-2H-1-苯并吡喃-3-羧酸乙酯
• 中文别名: (3E)-3-[乙氧基(羟基)甲亚基]-2H-色烯-2,4(3H)-二酮
• 英文名称: 3-ethoxycarbonyl-4-hydroxycoumarin
• 英文别名: 4-hydroxy-2-oxo-2H-chromene-3-carboxylate；ethyl 4-hydroxy-2-oxo-2H-chromene-3-carboxylate；4-hydroxy-2-oxo-2H-chromene-3-carboxylic acid ethyl ester；3-carbethoxy-4-hydroxy-coumarin；ethyl 4-hydroxy-2-oxochromene-3-carboxylate
• CAS: 1821-20-1
• 化学式: C₁₂H₁₀O₅
• mdl: MFCD00047639
• 分子量: 234.208
• InChiKey: RAGGBDBRGYOOED-UHFFFAOYSA-N

物化性质

• 熔点：
  139-140 °C
• 沸点：
  414.6±45.0 °C(Predicted)
• 密度：
  1.426±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  4-羟基-2-氧代-2H-1-苯并吡喃-3-羧酸乙酯 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 以96%的产率得到4-羟基香豆素
  参考文献：
  名称：

  Gupta, Arun K. Das; Chatterjee, Rabindra M.; Das, Kaustubh R., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 6, p. 511

  摘要：

  DOI：
• 作为产物：
  描述：

  阿司匹林 在 乙醇 、 sodium 、 sodium hydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 27.0h， 生成 4-羟基-2-氧代-2H-1-苯并吡喃-3-羧酸乙酯
  参考文献：
  名称：

  Functionalized 4-Hydroxy Coumarins: Novel Synthesis, Crystal Structure and DFT Calculations

  摘要：

  一种新的短步骤方法学已被开发用于功能化香豆素的高产率合成，该方法从N-羟基琥珀酰亚胺酯的O-乙酰水杨酸作为活化前体开始。该过程基于在温和反应条件下进行的串联C-酰化-环化反应。3-甲氧羰基-4-羟基香豆素的结构已通过X射线衍射分析确定，并通过DFT计算优化参数与其几何结构进行了比较。

  DOI：

  10.3390/molecules16010384

文献信息

• 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。
• Ring closure and rearrangement reactions of 4-azido-2-oxoquinoline-3-carboxylates and 4-azidocoumarin-3-carboxylates
  作者：Wolfgang Stadlbauer、Susanne Prattes、Werner Fiala

  DOI：10.1002/jhet.5570350322

  日期：1998.5

  4-Azido-2-oxoquinoline-3-carboxylates and 4-azidocoumarin-3-carboxylates 6, which were obtained from the corresponding 4-hydroxy derivatives 1 via 4-tosylates 2 or 4-chloro compounds 4, cyclized upon thermolysis to 3-alkoxyisoxazolo[4,3-c]quinolin-4(5H)-ones or the corresponding coumarins 8, whereas at slightly higher temperatures a 3-O, 4-O-rearrangement took place to give the 4-alkoxy-isoxazolo[4

  通过相应的4-羟基衍生物1经由4-甲苯磺酸酯2或4-氯化合物4从相应的4-羟基衍生物1中获得4-叠氮基-2-氧代喹啉-3-羧酸盐和4-叠氮杂多古灵-3-羧酸盐6，将它们在热解后环化成3-烷氧基异恶唑[ 4,3- c ]喹啉-4（5 H）-或相应的香豆素8，而在稍高的温度下，发生3- O，4- O重排，得到4-烷氧基-异恶唑[4]。 ，3- c ]-喹啉-3-酮和相应的香豆素9.借助差示扫描量热法可以容易地获得必要的反应条件。
• 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。
• 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.
• Enol-Ugi Reaction of Hydroxycoumarins: Straightforward Synthesis of Amino Acid Derived Coumarin Enamines
  作者：Ana Neo、Carlos Marcos、Teresa Castellano

  DOI：10.1055/s-0034-1380436

  日期：——

  Hydroxycoumarins containing electron-withdrawing groups have been successfully used as acidic components in Ugi-type multicomponent condensations with imines and isocyanides. The reaction takes place smoothly at room temperature, with no need of catalysis, affording 3- and 4-coumarin enamines in a highly convergent manner. Key to this transformation is the conjugate addition--elimination rearrangement on the primary adduct, irreversibly leading to the final product.