(5-methoxybenzofuran-2-yl)(4-methoxyphenyl)methanone | 383153-28-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5-methoxybenzofuran-2-yl)(4-methoxyphenyl)methanone
• 英文别名: 5-methoxy-2-(p-methoxybenzoyl)benzofuran；(5-Methoxy-1-benzofuran-2-yl)-(4-methoxyphenyl)methanone
• CAS: 383153-28-4
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: GWNOOKMIQWTZTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2Z)-5-methoxy-2-[(4-methoxyphenyl)methylidene]-1-benzofuran-3-one 在 盐酸 、 manganese(IV) oxide 、 sodium tetrahydroborate 、 水 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 2.25h， 生成 (5-methoxybenzofuran-2-yl)(4-methoxyphenyl)methanone
  参考文献：
  名称：

  A straightforward conversion of aurones to 2-benzoylbenzofurans: transformation of one class of natural products into another

  摘要：

  The naturally occurring aurones (2-benzylidene-3(2H)-benzofuran-3-ones) can be easily converted to another class of natural products 2-benzoylbenzo[b]furans, via an effective reduction, acid-mediated rearrangement, and oxidation cascade. This easy conversion was conducted without purification of intermediates. This straightforward conversion may be considered as a possible biosynthesis pathway of 2-benzoylbenzo[b]furans in plants. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.011

文献信息

• Syntheses of 2-Aroyl Benzofurans through Cascade Annulation on Arynes
  作者：Pashikanti Gouthami、Lahu N. Chavan、Rambabu Chegondi、Srivari Chandrasekhar

  DOI：10.1021/acs.joc.8b00360

  日期：2018.3.16

  The highly efficient and expedient route for the syntheses of 2-aroyl benzofurans has been developed via the cascade [2+2] followed by a [4+1] annulation on arynes. The overall transformation proceeded through the formation of ortho-quinone methide by the insertion of transient aryne into N,N-dimethylformamide and subsequent trapping with sulfur ylide. Moreover, this transformation has a broad range

  通过级联[2 + 2]，然后在芳烃上进行[4 + 1]环化，已经开发出了2-芳酰基苯并呋喃的高效合成途径。通过将瞬时的芳烃插入N，N-二甲基甲酰胺中，然后用硫内鎓盐捕集，通过形成邻醌甲基化物来进行整体转化。而且，该转变具有高官能团耐受性的广泛的基板范围。该新反应已成功用于有效的CYP19芳香酶抑制剂的合成和对生物活性复合物雌酮的后期功能化。
• A straightforward conversion of aurones to 2-benzoylbenzofurans: transformation of one class of natural products into another
  作者：Samir Yahiaoui、Marine Peuchmaur、Ahcène Boumendjel

  DOI：10.1016/j.tet.2011.08.011

  日期：2011.10

  The naturally occurring aurones (2-benzylidene-3(2H)-benzofuran-3-ones) can be easily converted to another class of natural products 2-benzoylbenzo[b]furans, via an effective reduction, acid-mediated rearrangement, and oxidation cascade. This easy conversion was conducted without purification of intermediates. This straightforward conversion may be considered as a possible biosynthesis pathway of 2-benzoylbenzo[b]furans in plants. (C) 2011 Elsevier Ltd. All rights reserved.