(E)-methyl 3-(7-hydroxy-4-oxo-4H-chromen-3-yl)acrylate | 1412410-81-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (E)-methyl 3-(7-hydroxy-4-oxo-4H-chromen-3-yl)acrylate
• 英文别名: methyl (E)-3-(7-hydroxy-4-oxochromen-3-yl)prop-2-enoate
• CAS: 1412410-81-1
• 化学式: C₁₃H₁₀O₅
• 分子量: 246.219
• InChiKey: QUSWDLWAFXVCFJ-GORDUTHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  (E)-methyl 3-(7-hydroxy-4-oxo-4H-chromen-3-yl)acrylate 、 间硝基苯胺 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以34%的产率得到5-(2,4-dihydroxybenzoyl)-1-(3-nitrophenyl)pyridin-2(1H)-one
  参考文献：
  名称：

  Re-cyclization of 3-(E)-methyl 3-(4-oxo-4H-chromen-3-yl)acrylate with amines and their potential mechanism

  摘要：

  The synthesis of 2-pyridone derivatives from different substituted amines and various 3-(E)-methyl 3-(4-oxo-4H-chromen-3-yl)acrylate derivatives was proposed and described. The optimized reaction conditions and the generality of the reaction were investigated, respectively. Moreover, less side products could be formed than the traditional method. Finally, based on the fact that (E)-methyl 2-(7-methoxy-4-oxo-3-((phenylamino)methylene)chroman-2-yl)acetate was separated and determined via X-ray single crystal diffraction, we could propose an interesting and reasonable reaction mechanism for the first time. The reaction could render this method particularly attractive for the efficient preparation of biologically and medicinally interesting molecules. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.032
• 作为产物：
  描述：

  3-甲酰基-4-氧-4H-色满-7-乙酸盐 在 吡啶 、 硫酸 作用下， 反应 13.5h， 生成 (E)-methyl 3-(7-hydroxy-4-oxo-4H-chromen-3-yl)acrylate
  参考文献：
  名称：

  Synthesis, Antiproliferative, and c-Src Kinase Inhibitory Activities of 4-Oxo-4H-1-benzopyran Derivatives

  摘要：

  A new class of 4‐oxo‐4H‐1‐benzopyran derivatives were synthesized and their antiproliferative activity examined against a panel of three human cancer cell lines, that is, breast carcinoma (MDA‐MB‐468), ovarian adenocarcinoma (SK‐OV‐3), and colorectal adenocarcinoma (HT‐29). Two compounds, that is, 3‐hexyl‐7,8‐dihydroxy‐4‐oxo‐4H‐1‐benzopyran and (E)‐ethyl 3‐(7‐methoxy‐4‐oxo‐4H‐1‐benzopyran‐3‐yl)acrylate were found to be potent against all three cancer cell lines studied at 50 μM concentration. Also, the inhibitory potency of the compounds was evaluated against active Src kinase. A few of these compounds exhibited modest Src kinase inhibitory activity (IC50 = 52–57 μM). Structure‐activity relationship studies with respect to the nature and position of substituents on the lead compounds could be further exploited for the design and development of more potent antiproliferative agents and/or Src kinase inhibitors.

  DOI：

  10.1002/jhet.2106

文献信息

• Efficient Heck cross-coupling of 3-iodo-benzopyrones with olefins under microwave irradiation without phosphine
  作者：Yikai Zhang、Zhiliang Lv、Hanyu Zhong、Mingfeng Zhang、Tao Zhang、Wannian Zhang、Ke Li

  DOI：10.1016/j.tet.2012.09.017

  日期：2012.11

  different terminal olefins with various 3-iodo-benzopyrones including sterically hindered, electron-rich, electron-neutral, and electron-deficient is developed. It proceeded faster and generally gave good to excellent yields under microwave irradiation, phosphine-free, and air condition. The reaction could render this method particularly attractive for the efficient preparation of biologically and

  研究了不同末端烯烃与各种3-碘-苯并吡喃酮的高效，有效的微波辅助Heck交叉偶联，包括空间位阻，富电子，电子中性和电子缺陷的3-碘-苯并吡喃酮。在微波辐射，无磷化氢和空气条件下，它进行得更快，并且通常具有优异的收率。该反应可使该方法对于有效制备生物学和医学上感兴趣的分子特别有吸引力。
• Heck Cross-Coupling Reactions in Ionic Liquid mediated Pd Nanocatalysts
  作者：Prashant Gautam、Vivek Srivastava

  DOI：10.2174/1570178617999200723124636

  日期：2021.5

  of palladium nanoparticles by using a series of palladium metal precursors and ionic liquids. All the materials went for XRD, TEM, and ICPOES analysis, before going to Heck cross-coupling reaction as a catalyst. We evaluated the catalytic performance of our developed IL#Pd MNP catalyst over Heck cross-coupling reaction between different terminal olefins with various 3-iodo-benzopyrones, including sterically

  我们使用一系列钯金属前体和离子液体直接合成了18种不同类型的钯纳米颗粒。在进行Heck交叉偶联反应作为催化剂之前，所有材料都要进行XRD，TEM和ICPOES分析。我们评估了我们开发的IL＃Pd MNP催化剂在不同末端烯烃与各种3-碘-苯并吡喃酮之间的Heck交叉偶联反应（包括位阻，富电子，电子中性和电子不足的系统）上的催化性能。我们在无膦反应条件下以良好的平均收率获得了Heck交叉偶联反应产物，并具有6倍的催化剂循环利用优势。