3-phenylbenzofuran-2-carbaldehyde | 57329-33-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3-phenylbenzofuran-2-carbaldehyde
• 英文别名: 2-Formyl-3-phenyl-benzofuran；3-Phenyl-1-benzofuran-2-carbaldehyde
• CAS: 57329-33-6
• 化学式: C₁₅H₁₀O₂
• 分子量: 222.243
• InChiKey: ZBSLKAYNXNYAOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  马尿酸 、 3-phenylbenzofuran-2-carbaldehyde 在 sodium acetate 、 乙酸酐 作用下， 生成 2-phenyl-4-(3-phenyl-benzofuran-2-ylmethylen)-4H-oxazol-5-one
  参考文献：
  名称：

  Chatterjea, Journal of the Indian Chemical Society, 1956, vol. 33, p. 339,344

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(1-羟基-1-苯基丙-2-炔基)苯酚 在 氧气 、 iron(II) chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 以71%的产率得到3-phenylbenzofuran-2-carbaldehyde
  参考文献：
  名称：

  Synergistic Gold and Iron Dual Catalysis: Preferred Radical Addition toward Vinyl–Gold Intermediate over Alkene

  摘要：

  A dual catalytic approach enlisting gold and iron, synergy is described. This method offers readily access to substituted heterocycle aldehydes via oxygen radical addition to vinyl-gold intermediates under Fe catalyst assistance. This system shows good functional group compatibility for the generation of substituted oxazole, indole, and benzofuran aldehydes. Mechanistic evidence greatly supports selective radical addition to an: activated vinyl-Au double bond over alkene. This unique discovery offers a new avenue with great potential to further extend the synthetic power and versatility of gold catalysis.

  DOI：

  10.1021/jacs.5b05415

文献信息

• Preparation of Highly Functionalised Benzofurans from<i>ortho</i>-Hydroxyphenones and Dichloroethylene: Applications and Mechanistic Investigations
  作者：Florian Schevenels、Bernard Tinant、Jean-Paul Declercq、István E. Markó

  DOI：10.1002/chem.201201505

  日期：2013.3.25

  Highly functionalised benzofurans have been prepared from ortho‐hydroxyphenones and 1,1‐dichloroethylene. The key intermediate, a chloromethylene furan, smoothly rearranged into the corresponding benzofuran carbaldehyde under acidic conditions. Some mechanistic investigations have been performed and several biologically active benzofurans have been synthesised.

  高度功能化的苯并呋喃是由邻羟基苯甲酮和1,1-二氯乙烯制备的。关键中间体氯亚甲基呋喃在酸性条件下平稳重排成相应的苯并呋喃甲醛。已经进行了一些机理研究，并且已经合成了几种具有生物活性的苯并呋喃。
• Diphenyl-Diselenide-Mediated Domino Claisen-Type Rearrangement/Cyclization of Propargylic Aryl Ethers: Synthesis of Naphthofuran-2-carboxaldehyde Derivatives
  作者：Jun-Dan Fang、Xiao-Biao Yan、Wu-Jie Lin、Yi-Chuan Zhao、Xue-Yuan Liu

  DOI：10.1021/acs.orglett.9b02942

  日期：2019.9.20

  A diphenyl-diselenide-mediated Claisen-type rearrangement/cyclization of propargylic aryl ethers under metal-free conditions is developed, affording various naphthofuran-2-carboxaldehydes in moderate to excellent yield. The broad substrate scope and excellent functional group compatibility suggest that it can be a straightforward and powerful method to access naphthofuran-2-carboxaldehydes in a highly

  在无金属条件下开发了炔丙基芳基醚的二苯基-二硒化物介导的克莱森型重排/环化反应，以中等至极好的收率提供了各种萘呋喃-2-甲醛。广泛的底物范围和出色的官能团相容性表明，它可以是一种以高度区域选择性的方式访问萘呋喃-2-甲醛的简单有效的方法。此外，该反应可以按比例放大至克级。
• Transient‐Ligand‐Enabled <i>ortho</i> ‐Arylation of Five‐Membered Heterocycles: Facile Access to Mechanochromic Materials
  作者：Bijin Li、Kapileswar Seth、Ben Niu、Lei Pan、Huiwen Yang、Haibo Ge

  DOI：10.1002/anie.201713357

  日期：2018.3.19

  example of a direct arylation of heteroarenes by a transient‐ligand‐directed strategy without the need to construct and deconstruct the directing group. A wide range of heteroarenes undergoes the coupling with diverse aryl iodides to assemble a large library of highly selective and functionalized 3‐arylthiophene‐2‐carbaldehydes. This route provides an opportunity to rapidly access new mechanofluorochromic

  本文报道的是通过瞬态配体定向策略直接芳基杂芳基化的第一个示例，而无需构建和解构定向基团。各种各样的杂芳基经过与各种芳基碘化物的偶联而组装成一个高度选择性和功能化的3-芳基噻吩-2-甲醛的大型文库。这种途径提供了快速获取新的机械氟致变色材料的机会。此外，通过对常见结构核心进行容易的官能团修饰，首次公开了具有红移和蓝移变色趋势的机械变色发光剂的新策略。
• Efficient and Connective Assembly of Highly Functionalized Benzofurans Using <i>o</i>-Hydroxyphenones and Dichloroethylene
  作者：Florian Schevenels、István E. Markó

  DOI：10.1021/ol300186s

  日期：2012.3.2

  The preparation of highly functionalized benzofurans by a unique and connective transformation is reported. Base-catalyzed condensation of o-hydroxyphenones with 1,1-dichloroethylene generates the corresponding chloromethylene furans. These labile intermediates undergo a facile rearrangement into benzofuran carbaldehydes under mild acidic conditions.
• CHATTERJEA J. N.; BHAKTA C.; LAL S., INDIAN J. CHEM., 1978, B 16, NO 7 567-569
  作者：CHATTERJEA J. N.、 BHAKTA C.、 LAL S.

  DOI：——

  日期：——