(Z)-2-(2-(allyloxy)benzylidene)-7-methoxybenzofuran-3(2H)-one | 1402344-78-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 橙酮类黄酮
• 英文名称: (Z)-2-(2-(allyloxy)benzylidene)-7-methoxybenzofuran-3(2H)-one
• 英文别名: (2Z)-7-methoxy-2-[(2-prop-2-enoxyphenyl)methylidene]-1-benzofuran-3-one
• CAS: 1402344-78-8
• 化学式: C₁₉H₁₆O₄
• 分子量: 308.334
• InChiKey: QQJDDUJTLONYSU-ATVHPVEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-甲氧基苯氧乙酸 在 ethylenediamine Tetraacetic Acid 作用下， 以 乙腈 为溶剂， 反应 9.3h， 生成 (Z)-2-(2-(allyloxy)benzylidene)-7-methoxybenzofuran-3(2H)-one
  参考文献：
  名称：

  Synthesis and Structural Characterization of 2-Benzylidenebenzofuran-3-(2H)-Ones

  摘要：

  Novel aurone derivatives e.g. 2-(2-(3-methylbut-2-enyloxy)benzylidene)benzofuran-3(2H)-one (3a), 2-(2-(allyloxy)benzylidene)-7-methoxybenzofuran-3(2H)-one (3b), and 2-(5-bromo-2-(3-methylbut-2-enyloxy)benzylidene)-6-hydroxybenzofuran-3(2H)-one (3c) were synthesized. All these compounds were characterized by IR, H-1 and C-13 NMR, and Mass spectroscopy. Finally, the crystal structures were solved by single crystal X-ray diffraction data and the structures were analyzed in terms of supramolecular interactions. [Supplementary materials are available for this article. Go to the publisher's online edition of Molecular Crystals and Liquid Crystals for the following free supplemental resource(s): supplemental figures 1-12; Spectral data (IR, NMR, MS, and HRMS) of the compounds 3a, 3b and 3c are available in the supporting information in .pdf format. Crystallographic information files (.cif) of compounds 3a, 3b, and 3c are available in the electronic format.]

  DOI：

  10.1080/15421406.2013.782179

文献信息

• Ethylenediamine diacetate (EDDA) mediated synthesis of aurones under ultrasound: Their evaluation as inhibitors of SIRT1
  作者：Khanapur Manjulatha、S. Srinivas、Naveen Mulakayala、D. Rambabu、M. Prabhakar、Kalle M. Arunasree、Mallika Alvala、M.V. Basaveswara Rao、Manojit Pal

  DOI：10.1016/j.bmcl.2012.08.017

  日期：2012.10

  of functionalized aurones has been accomplished via the reaction of benzofuran-3(2H)-one with a range of benzaldehydes in the presence of a mild base EDDA under ultrasound. A number of aurones were synthesized (within 5–30 min) and the molecular structure of a representative compound determined by single crystal X-ray diffraction study confirmed Z-geometry of the C–C double bond present within the

  在超声波下，在温和的碱EDDA存在下，苯并呋喃3（2 H）-one与一系列苯甲醛的反应已实现了功能化金氧烷的改进合成。合成了许多金氧化合物（在5-30分钟内），通过单晶X射线衍射研究确定的代表性化合物的分子结构证实了分子中存在的C-C双键的Z-几何形状。某些合成的化合物在体外显示出对两种癌细胞系具有SIRT1抑制作用以及抗增殖特性。化合物3a [（Z）-2-（5-溴-2-羟基亚苄基）苯并呋喃-3（2 H）-一]被确定为SIRT1的有效抑制剂（IC 50 = 1μM），这显示p53乙酰化的剂量依赖性增加，导致细胞凋亡的诱导。