(Z)-2-(3,5-dimethoxybenzylidene)benzofuran-3(2H)-one | 927429-54-7

• 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-(3,5-dimethoxybenzylidene)benzofuran-3(2H)-one
• 英文别名: 3',5'-dimethoxyaurone；(2Z)-2-[(3,5-dimethoxyphenyl)methylidene]-1-benzofuran-3-one
• CAS: 927429-54-7
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: SNEMOVVUUZWIGF-SXGWCWSVSA-N

物化性质

• 熔点：
  153-155 °C(Solv: chloroform (67-66-3); hexane (110-54-3))
• 沸点：
  464.0±45.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-2-(3,5-dimethoxybenzylidene)benzofuran-3(2H)-one 在 sodium azide 作用下， 反应 0.5h， 以83%的产率得到[5-(3,5-dimethoxyphenyl)-2H-1,2,3-triazol-4-yl](2-hydroxyphenyl)methanone
  参考文献：
  名称：

  从Aurones异常三唑合成

  摘要：

  试图通过铜催化的叠氮化制备叠氮基取代的金酮的尝试未能获得所需的产物，而是导致了异常的三唑形成反应。进一步的努力表明该反应不需要铜，而只需在极性非质子溶剂中简单地用叠氮化钠进行热处理即可。在该反应中容许各种各样的取代方式，以适中至优异的产率提供令人感兴趣的水杨基取代的三唑。尽管机理尚不清楚，但是考虑到相应硫代黄酮在反应上的失败，简单的消除/环化途径似乎不太可能，后者具有更好的硫醇离去基团。无论如何，这些易于获得的多功能化合物的潜在用途应引起更多的兴趣和应用。

  DOI：

  10.1055/s-0040-1708019
• 作为产物：
  描述：

  3-苯并呋喃酮 、 3,5-二甲氧基苯甲醛 在 aluminum oxide 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到(Z)-2-(3,5-dimethoxybenzylidene)benzofuran-3(2H)-one
  参考文献：
  名称：

  路易斯酸促进的迈克尔加成和扩环级联用于构建含氮中型环。

  摘要：

  开发了路易斯酸促进的氮杂二烯和环丁胺的环化反应。该反应通过迈克尔加成和扩环级联进行，以中等到高收率提供具有广泛范围的相应含氮中型环。还使用手性碱探索了该反应的催化不对称形式。

  DOI：

  10.3390/molecules28041650

文献信息

• Synthesis and Insect Antifeedant Activity of Aurones against <i>Spodoptera litura</i> Larvae
  作者：Masanori Morimoto、Hiromi Fukumoto、Toki Nozoe、Ai Hagiwara、Koichiro Komai

  DOI：10.1021/jf062562t

  日期：2007.2.1

  A series of aurones were prepared from various phenols via phenoxy acetic acids and coumaranones and evaluated for insect antifeedant activity against the common cutworm (Spodoptera litura). The naturally occurring aurone was most active at an ED50 of 0.12 mu mol/cm(2). The synthetic precursor, coumaranones, showed that the introduction of methoxyl and methyl groups to the benzene ring increased insect antifeedant activity. Similarly, the tested aurones showed that the introduction of methoxyl group to the A and/or B rings increased the insect antifeedant activity, but 4,5,6- and 3',4',5'-trisubstituted compounds did not show this activity in this test. The hydroxylation of aurones in the B ring should be disadvantageous for insect antifeedant activity against S. litura. Although the melting points did not correlate well with the insect antifeedant activity, compounds that were nearly inactive had high melting points. A significant correlation was noted between biological activity (pED(50)) and a hydrogen-bonding parameter calculated from the R-f value obtained from SiOH thin-layer chromatography and a lipophilicity parameter (log k) calculated from the retention time in ODS high-performance liquid chromatography. The respective correlation coefficients (r) were -0.83 and -0.70. The introduction of alkoxy and alkyl groups along with adequate hydrogen bonding seems to contribute to the antifeedant activity of the compounds tested.
• Base-catalyzed cascade [3 + 2] spiroannulation/aromatization of in situ generated tosyldiazomethane (TsDAM) with (Z)-aurones: An efficient access to polysubstituted pyrazole derivatives
  作者：Jie Huang、Shaofa Sun、Ping Ma、Clairissa Yom、Yalan Xing、Yang Wu、Gangqiang Wang

  DOI：10.1016/j.tetlet.2022.153840

  日期：2022.6
• An Unusual Triazole Synthesis from Aurones
  作者：Scott T. Handy、Arjun Kafle、Shrijiana Bhattarai

  DOI：10.1055/s-0040-1708019

  日期：2020.8

  Attempts to prepare azido-substituted aurones via a copper-catalyzed azidation failed to afford the desired product, but instead resulted in an unusual triazole formation reaction. Further efforts noted that copper was not required for this reaction, but simply thermal treatment with sodium azide in a polar aprotic solvent. A wide range of substitution patterns were tolerated in this reaction to afford

  试图通过铜催化的叠氮化制备叠氮基取代的金酮的尝试未能获得所需的产物，而是导致了异常的三唑形成反应。进一步的努力表明该反应不需要铜，而只需在极性非质子溶剂中简单地用叠氮化钠进行热处理即可。在该反应中容许各种各样的取代方式，以适中至优异的产率提供令人感兴趣的水杨基取代的三唑。尽管机理尚不清楚，但是考虑到相应硫代黄酮在反应上的失败，简单的消除/环化途径似乎不太可能，后者具有更好的硫醇离去基团。无论如何，这些易于获得的多功能化合物的潜在用途应引起更多的兴趣和应用。
• A Lewis Acid-Promoted Michael Addition and Ring-Expansion Cascade for the Construction of Nitrogen-Containing Medium-Sized Rings
  作者：Jiaming Wang、Jia Li、Changgui Zhao

  DOI：10.3390/molecules28041650

  日期：——

  A Lewis acid-promoted annulation of azadienes and cyclobutamines was developed. This reaction proceeded through Michael addition and ring-expansion cascade, affording the corresponding nitrogen-containing medium-sized rings with a broad scope in moderate to high yields. The catalytic asymmetric version of this reaction has also been explored using a chiral base.

  开发了路易斯酸促进的氮杂二烯和环丁胺的环化反应。该反应通过迈克尔加成和扩环级联进行，以中等到高收率提供具有广泛范围的相应含氮中型环。还使用手性碱探索了该反应的催化不对称形式。