(E)-methyl 3-(7-methoxy-4-oxo-4H-chromen-3-yl)acrylate | 42059-83-6

• 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-methoxy-4-oxo-4H-chromen-3-yl)acrylate
• 英文别名: trans-Methyl-3-(7-methoxy-4-oxo-4H-1-benzopyran-3)acrylat；Methyl-trans-3-(7-methoxy-4-oxo-4H-1-benzopyran-3)-acrylat；methyl (E)-3-(5-hydroxy-7-methoxy-4-oxo-4H-chromen-3-yl)acrylate；methyl (E)-3-(7-methoxy-4-oxochromen-3-yl)prop-2-enoate
• CAS: 42059-83-6
• 化学式: C₁₄H₁₂O₅
• 分子量: 260.246
• InChiKey: DPRAXBREIRZSKO-ZZXKWVIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-methyl 3-(7-methoxy-4-oxo-4H-chromen-3-yl)acrylate 、 对乙氧基苯胺 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以80%的产率得到1-(4-ethoxyphenyl)-5-(2-hydroxy-4-methoxybenzoyl)pyridin-2(1H)-one
  参考文献：
  名称：

  Design, Synthesis, and Antihepatitis B Virus Activities of Novel 2-Pyridone Derivatives

  摘要：

  A series of novel 2-pyridone derivatives were synthesized and evaluated for their antihepatitis B virus (HBV) activity and cytotoxicity in vitro. Moderate to good activity against HBV DNA replication was observed in these 2-pyridone analogues. The most active compounds were 5d and 61, with good inhibitory activity against HBV DNA replication (IC50 = 0.206 and 0.12 mu M, respectively) and remarkable high selectivity (selectivity indexes of >532 and 467, respectively). A pharmacophore model of the synthesized compounds was proposed by the GASP program. The pharmacophore model consists of three hydrophobic points, four HBA points, and one HBD point. The 2-pyridone derivatives represent a novel class of HBV inhibitors, which are worth further optimization.

  DOI：

  10.1021/jm901237x
• 作为产物：
  描述：

  7-甲氧基-4H-色烯-4-酮 在 吡啶 、 碘 、 palladium diacetate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.08h， 生成 (E)-methyl 3-(7-methoxy-4-oxo-4H-chromen-3-yl)acrylate
  参考文献：
  名称：

  在没有磷化氢的微波辐射下3-碘-苯并吡喃酮与烯烃的有效Heck交叉偶联

  摘要：

  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。

  DOI：

  10.1016/j.tet.2012.09.017

文献信息

• Re-cyclization of 3-(E)-methyl 3-(4-oxo-4H-chromen-3-yl)acrylate with amines and their potential mechanism
  作者：Yikai Zhang、Zhiliang Lv、Mingfeng Zhang、Ke Li

  DOI：10.1016/j.tet.2013.08.032

  日期：2013.10

  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.
• NOHARA A.; KURIKI H.; SAIJO T.; UKAWA K.; MURATA T.; KANNO M.; SANNO J., J. MED. CHEM. <JMCM-AR>, 1975, 18, NO 1, 34-37
  作者：NOHARA A.、 KURIKI H.、 SAIJO T.、 UKAWA K.、 MURATA T.、 KANNO M.、 SANNO J.

  DOI：——

  日期：——