(E)-N,N-二乙基-3-(4-氧代-4H-1-苯并吡喃-3-基)丙烯酰胺 | 1005752-36-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: (E)-N,N-二乙基-3-(4-氧代-4H-1-苯并吡喃-3-基)丙烯酰胺
• 英文名称: (E)-N,N-diethyl-3-(4-oxo-4H-chromen-3-yl)prop-2-enamide
• 英文别名: (E)-N,N-diethyl-3-(4-oxo-4H-1-benzopyran-3-yl)acrylamide；(E)-N,N-diethyl-3-(4-oxochromen-3-yl)prop-2-enamide
• CAS: 1005752-36-2
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: UZMVSMBFDSEWMQ-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙烯,四甲氧基- 、 (E)-N,N-二乙基-3-(4-氧代-4H-1-苯并吡喃-3-基)丙烯酰胺 在 三氟化硼乙醚 作用下， 以 1,1,2,2-四氯乙烷 、 二氯甲烷 为溶剂， 反应 192.0h， 以40%的产率得到N,N-diethyl-3,4-dimethoxy-9-oxo-9H-xanthene-2-carboxamide
  参考文献：
  名称：

  Electron-Deficient Dienes. 5. An Inverse-Electron-Demand Diels−Alder Approach to 2-Substituted 4-Methoxyxanthones and 3,4-Dimethoxyxanthones

  摘要：

  Several 4-methoxyxanthones and 3,4-dimethoxyxanthones were synthesized in good yield via inverse-electron-demand Diels-Alder (IEDDA) driven domino reactions between a series of electron-deficient chromone-fused dienes with 1-(2,2-dimethoxyvinyl)pyrrolidine or tetramethoxyethene, respectively.

  DOI：

  10.1021/ol702614b
• 作为产物：
  描述：

  2'-羟基苯乙酮 在 吡啶 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.5h， 生成 (E)-N,N-二乙基-3-(4-氧代-4H-1-苯并吡喃-3-基)丙烯酰胺
  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