methyl 6-methyl-2-oxo-2H-chromene-3-carboxylate | 1026924-93-5

• 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: methyl 6-methyl-2-oxo-2H-chromene-3-carboxylate
• 英文别名: methyl 6-methylcoumarin-3-carboxylate；3-(methoxycarbonyl)-6-methyl-2H-chromen-2-one；methyl 6-methyl-2-oxochromene-3-carboxylate
• CAS: 1026924-93-5
• 化学式: C₁₂H₁₀O₄
• 分子量: 218.209
• InChiKey: VZPUFTUKASFQKA-UHFFFAOYSA-N

物化性质

• 熔点：
  127-128 °C(Solvent: Ethanol)
• 沸点：
  380.1±42.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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 6-methyl-2-oxo-2H-chromene-3-carboxylate 、 对氨基苯腈 在 potassium tert-butylate 、 3-(2,6-diisopropylphenyl)-1-(2-pyridyl)imidazolium bromide 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以82%的产率得到
  参考文献：
  名称：

  甲基酯作为交叉偶联亲电试剂：酰胺键的直接合成

  摘要：

  酰胺键的形成和过渡金属催化的交叉偶联是有机合成中最常用的两种化学反应。最近，当Pd和Ni催化剂通过氧化加成裂解酯中存在的强C-O键时，发现这两个反应族之间存在重叠。当使用简单的甲酯和乙酯时，这种转化为经典的酰胺键形成提供了有力的替代方法，后者通常具有化学计量活化剂的特征。迄今为止，几乎没有氧化还原活性催化剂被证明可以激活烷基酯的C（酰基）-O键，这使得当需要优化具有挑战性的反应时，很难进行明智的筛选。我们证明了带有多种NHC，磷化氢，

  DOI：

  10.1021/acscatal.9b00884
• 作为产物：
  描述：

  5-甲基水杨醛 、 丙二酸二甲酯 在 lipozyme TL IM from Thermomyces lanuginosus 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.17h， 生成 methyl 6-methyl-2-oxo-2H-chromene-3-carboxylate
  参考文献：
  名称：

  连续流微反应器中由嗜热霉菌的脂酶 TL IM 催化的含糖香豆素衍生物串联合成的可持续创新

  摘要：

  我们开发了一种高效且环保的两步串联方法，用于在连续流动微反应器中由嗜热霉菌的脂酶 TL IM 催化合成含糖香豆素衍生物。与其他方法相比，该工作的显着特点包括绿色反应条件、停留时间短（50分钟）、催化剂更容易获得、生物催化反应过程高效且易于控制。这种使用连续流动技术的香豆素衍生物的两步串联合成是一个概念证明，它开启了酶促微反应器在香豆素衍生物生物转化中的应用。

  DOI：

  10.1039/d0ra00879f

文献信息

• Synthesis of coumarin-3-carboxylic esters via FeCl3-catalyzed multicomponent reaction of salicylaldehydes, Meldrum's acid and alcohols
  作者：Xinwei He、Yongjia Shang、Yao Zhou、Zhiyu Yu、Guang Han、Wenjing Jin、Jiaojiao Chen

  DOI：10.1016/j.tet.2014.12.042

  日期：2015.2

  FeCl3-catalyzed multicomponent reaction was developed for the facile synthesis of coumarin-3-carboxylic ester derivatives in a highly atom-economic and environmentally friendly way. Using simple and cheaply available salicylaldehydes, Meldrum's acid and alcohols as the starting materials, the method needs no extra additives and features wide substrate scope, good functional group tolerance and mild reaction conditions

  开发了FeCl 3催化的多组分反应，以高度原子经济和环境友好的方式容易地合成香豆素-3-羧酸酯衍生物。该方法使用简单廉价的水杨醛，Meldrum的酸和醇作为起始原料，不需要额外的添加剂，并且具有广泛的底物范围，良好的官能团耐受性和温和的反应条件。
• Knoevenagel Reaction in [MMIm][MSO4]: Synthesis of Coumarins
  作者：Pedro Verdía、Francisco Santamarta、Emilia Tojo

  DOI：10.3390/molecules16064379

  日期：——

  The ionic liquid 1,3-dimethylimidazolium methyl sulfate, [MMIm][MSO4], together with a small amount of water (the amount taken up by the ionic liquid upon exposure to air), acts efficiently as both solvent and catalyst of the Knoevenagel condensation reactions of malononitrile with 4-substituted benzaldehydes, without the need for any other solvent or promoter, affording yields of 92%–99% within 2–7 min at room temperature. When L-proline is used as an additional promoter to obtain coumarins from o-hydroxybenzaldehydes, the reaction also proceeds in high yields. Work-up is very simple and the ionic liquid can be reused several times. Some of the coumarins obtained are described for the first time.

  离子液体1,3-二甲基咪唑鎓甲基硫酸盐[MMIm][MSO4]以及少量水（与空气接触时被离子液体吸收的水量）有效地作为溶剂和催化剂，实现了丙二腈与4-取代苯甲醛的Knoevenagel缩合反应，无需任何其他溶剂或促进剂，在室温下实现了92%–99%的高产率，反应时间为2–7分钟。当使用L-脯氨酸作为额外促进剂从邻羟基苯甲醛合成香豆素时，反应同样获得了高产率。后处理非常简单，离子液体可以重复使用多次。一些所获得的香豆素首次被描述。
• [EN] SMALL MOLECULE ANALOGS OF THE PROTEIN E4ORF1 IN THE TREATMENT AND PREVENTION OF METABOLIC DISORDERS<br/>[FR] ANALOGUES DE PETITES MOLÉCULES DE LA PROTÉINE E4ORF1 DANS LE TRAITEMENT ET LA PRÉVENTION DE TROUBLES MÉTABOLIQUES
  申请人：UNIV TEXAS TECH SYSTEM

  公开号：WO2020146449A1

  公开（公告）日：2020-07-16

  In an embodiment, the present disclosure pertains to compositions and methods for modulating cellular glucose uptake. In general, the methods include associating cells with the compositions of the present disclosure. In another aspect, the present disclosure pertains to compositions and methods to treat or prevent a disorder in a subject. The methods generally include administering the compositions of the present disclosure to the subject.

  在一种实施例中，本公开涉及调节细胞葡萄糖摄取的组合物和方法。通常，该方法包括将细胞与本公开的组合物相关联。另一方面，本公开涉及用于治疗或预防主体中疾病的组合物和方法。该方法通常包括向主体施用本公开的组合物。
• USE OF COUMARIN DERIVATIVES FOR THE PREPARATION OF DRUGS FOR TREATING SKIN DISEASES
  申请人：UNIVERSITE PIERRE ET MARIE CURIE (PARIS 6)

  公开号：US20170065555A1

  公开（公告）日：2017-03-09

  A compound of formula (I-1) wherein n equals 0 or 1, Z represents O or S, R1 represents one group chosen among the group consisting of hydrogen, C1-C7 alkyl, substituted, or not, by a halogen, a hydroxyl or a —O—R12 group, wherein R12 is a C1-C7 alkyl, a group —CH 2 —O—CO—R5 wherein R5 is chosen among a hydrogen atom and a C1-C7 alkyl, substituted or not by at least one halogen, a group —O—R13, wherein R13 is chosen among hydrogen and a C1-C7 alkyl, an amine or a —CH 2 -amine, R′1 represents a group chosen among hydrogen and —O—R14, wherein R14 is chosen among hydrogen and a C1-C7 alkyl, and R2 is chosen among the group consisting of a C1-C7 alkyl, a C3-C6 cycloalkyl, an aryl group, and an heteroaryl group for the treatment of pathologies involving excess activity of at least one member of the kallikrein family.
• Visible Light‐Induced Metal‐free Arylation of Coumarin‐3‐carboxylates with Arylboronic Acids
  作者：Swarnayu Banik、Aita Saikiran、Prathyusha Permula、K. S. Srivishnu、B. Sridhar、B. V. Subba Reddy

  DOI：10.1002/asia.202400042

  日期：2024.4.16

  The present work represents a novel methodology for the selective arylation of coumarin‐3‐carboxylates with arylboronic acids via a photochemical route, marking the first‐ever attempt for the direct alkenyl C−H arylation using rose bengal as a photocatalyst, which is a readily available and cost‐effective alternative to transition metal catalysis. The reaction proceeds smoothly in MeOH/H2O solvent media in the presence of radical initiator affording the arylated products in good yields (60–80 %). The reaction parameters such as visible light, radical initiator, oxidant, anhydrous solvent, and inert atmosphere play a crucial role for the success of this methodology. The substituents present on the substrate show a significant effect on the conversion. This study provides a valuable contribution to the field of organic synthesis offering a new and efficient approach to the arylation of coumarin‐3‐carboxylic acid esters with a broad substrate scope and high functional group tolerance. It is a versatile method and provides a direct access to biologically relevant 4‐arylcoumarin‐3‐carboxylates.