2-苯基苯并[e][1]苯并呋喃 | 14385-54-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 中文名称: 2-苯基苯并[e][1]苯并呋喃
• 英文名称: 2-phenylnaphtho[2,1-b]furan
• 英文别名: 2-phenylbenzo[e][1]benzofuran
• CAS: 14385-54-7
• 化学式: C₁₈H₁₂O
• 分子量: 244.293
• InChiKey: FTYUMOGCRQVDMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-苯基苯并[e][1]苯并呋喃 以32%的产率得到
  参考文献：
  名称：

  BASTIAN, G.;ROYER, R., EUR. J. MED. CHEM., 1984, 19, N 2, 157-160

  摘要：

  DOI：
• 作为产物：
  描述：

  苯并[e][1]苯并呋喃 在 3,3-二甲基-1-丁烯 、 C₂₅H₄₀O₂P₂Ru 、 palladium diacetate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 potassium hydroxide 作用下， 以 对二甲苯 为溶剂， 反应 37.0h， 生成 2-苯基苯并[e][1]苯并呋喃
  参考文献：
  名称：

  A Pincer Ruthenium Complex for Regioselective C–H Silylation of Heteroarenes

  摘要：

  A pincer Ru(II) catalyst for the highly efficient undirected silylation of O- and S-heteroarenes with (TMSO)(2)MeSiH and Et3SiH is described, producing heteroarylsilanes with exclusive C2-regioselectivity, good functional group tolerance, and high turnover numbers (up to 1960). The synthetic utility of the silylated products is demonstrated by Pd-catalyzed Hiyama-Denmark cross-coupling under mild conditions. One-pot, two-step silylation and coupling procedures have been also developed.

  DOI：

  10.1021/acs.orglett.6b02857

文献信息

• Palladium-Catalyzed Synthesis of Benzofurans and Coumarins from Phenols and Olefins
  作者：Upendra Sharma、Togati Naveen、Arun Maji、Srimanta Manna、Debabrata Maiti

  DOI：10.1002/anie.201305326

  日期：2013.11.25

  Triple CH functionalization: Palladium‐catalyzed synthesis of benzofurans and coumarins by reacting phenols and unactivated olefins is described. The reaction comprises sequential CH functionalization and shows diverse functional group compatibility. Preliminary mechanistic studies shed light into the possible mechanisms.

  三重CH官能化：描述了通过酚与未活化的烯烃反应，钯催化合成苯并呋喃和香豆素。该反应包括顺序的CH官能化，并显示出各种官能团相容性。初步的机理研究阐明了可能的机制。
• One-Step Synthesis of Substituted Benzofurans from <i>ortho</i> - Alkenylphenols <i>via</i> Palladium-Catalyzed CH Functionalization
  作者：Dejun Yang、Yifei Zhu、Na Yang、Qiangqiang Jiang、Renhua Liu

  DOI：10.1002/adsc.201600082

  日期：2016.6.2

  A dehydrogenative oxygenation of C(sp2)H bonds with intramolecular phenolic hydroxy groups has been developed, which provides a straightforward and concise access to structurally diversely benzofurans from ortho‐alkenylphenols. The reaction is catalyzed by palladium on carbon (Pd/C) without any oxidants and sacrificing hydrogen acceptors.

  C（的脱氢氧合SP 2）与分子内酚羟基H键已被开发，这提供了从结构上多样的苯并呋喃一个简单和简明的访问邻-alkenylphenols。该反应由钯/碳（Pd / C）催化，不带任何氧化剂且不牺牲氢受体。
• An efficient tandem elimination–cyclization–desulfitative arylation of 2-(gem-dibromovinyl)phenols(thiophenols) with sodium arylsulfinates
  作者：Wei Chen、Pinhua Li、Tao Miao、Ling-Guo Meng、Lei Wang

  DOI：10.1039/c2ob27232f

  日期：——

  An efficient tandem elimination–cyclization–desulfitative arylation of 2-(gem-dibromovinyl)phenols(thiophenols) with sodium arylsulfinates has been developed. In the presence of TBAF–PdCl2–Cu(OAc)2–NEt3, the reactions generated 2-arylbenzofurans(thiophenes) with good yields in one-pot under ligand-free conditions.

  开发了一种高效的串联去除、环化和去亚磺酰化芳基化反应，利用2-(gem-二溴乙烯基)酚（硫酚）与芳基亚磺酸钠反应。在TBAF–PdCl2–Cu(OAc)2–NEt3的催化下，该反应在无配体条件下以一锅法生成了产率良好的2-芳基苯并呋喃（硫烯）。
• Fabrication of an amyloid fibril-palladium nanocomposite: a sustainable catalyst for C–H activation and the electrooxidation of ethanol
  作者：Ramasamy Jayarajan、Rakesh Kumar、Jagriti Gupta、Gayathri Dev、Pradeep Kadu、Debdeep Chatterjee、Dhirendra Bahadur、Debabrata Maiti、Samir K. Maji

  DOI：10.1039/c8ta11134k

  日期：——

  used as a heterogeneous catalyst in C–H bond activation and the electrooxidation of ethanol. The study demonstrated α-Syn-PdNPs to be a superior heterogeneous catalyst for the synthesis of pharmaceutically valuable benzofuran, naphthofuran, coumarin and N-arylindole via C–H activation. Further, the electrooxidation of ethanol using α-Syn-PdNPs displayed an electrochemically active surface area of 160.6

  淀粉样蛋白是高度有序的纳米原纤维，其抗张强度与钢相似，因此可以抵抗极端的pH和温度。基于此原理，我们证明了以α-突触核蛋白（α-Syn）原纤维为模板，可以轻松合成钯，铜，铂，金和银纳米复合材料。我们表明，α-Syn-原纤维-钯纳米颗粒（α-Syn-PdNPs）复合材料可以用作C–H键活化和乙醇电氧化的非均相催化剂。研究表明，α-Syn-PdNPs是一种优异的非均相催化剂，可通过以下方法合成药学上有价值的苯并呋喃，萘并呋喃，香豆素和N-芳基吲哚。C–H激活。此外，使用α-Syn-PdNPs对乙醇进行的电氧化表现出160.6 m 2 g -1的电化学活性表面积，该表面积比先前报道的负载Pd纳米复合材料的值高得多。
• Acid-catalyzed cleavage of C–C bonds enables atropaldehyde acetals as masked C2 electrophiles for organic synthesis
  作者：Shaomin Chen、Minghao Li、Yanlong Gu

  DOI：10.1039/d1cc04000f

  日期：——

  Acid-catalyzed tandem reactions of atropaldehyde acetals were established for the synthesis of three important molecules, 2,2-disubstituted indolin-3-ones, naphthofurans and stilbenes. The synthesis was realized using novel reaction cascades, which involved the same two initial steps: (i) SN2′ substitution, in which the atropaldehyde acted as an electrophile; and (ii) oxidative cleavage of the carbon–carbon

  阿托醛缩醛的酸催化串联反应被建立用于合成三个重要分子，2,2-二取代 indolin-3-ones、萘并呋喃和芪。该合成是使用新的反应级联反应实现的，其中涉及相同的两个初始步骤：(i) S N 2' 取代，其中阿托醛充当亲电子试剂；(ii) 生成的苯乙醛类产物的碳-碳键的氧化裂解。与文献方法相比，本协议不仅避免使用昂贵的贵金属催化剂，而且操作简单。