3-ethyl-2-phenylbenzofuran | 59092-74-9

• 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
• 英文名称: 3-ethyl-2-phenylbenzofuran
• 英文别名: 3-Ethyl-2-phenyl-1-benzofuran；3-ethyl-2-phenyl-1-benzofuran
• CAS: 59092-74-9
• 化学式: C₁₆H₁₄O
• 分子量: 222.287
• InChiKey: CBCGDKQFYJZRFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 以65 mg的产率得到3-ethyl-2-phenylbenzofuran
  参考文献：
  名称：

  One-Pot Synthesis of Benzofurans via Palladium-Catalyzed Enolate Arylation with o-Bromophenols

  摘要：

  A one-pot synthesis of benzofurans which utilizes a palladium-catalyzed enolate arylation is described. The process demonstrates broad substrate scope and provides differentially substituted benzofurans in moderate to excellent yields. The utility of the method is further demonstrated by the synthesis of the natural product eupomatenoid 6 in three steps.

  DOI：

  10.1021/ol801510n

文献信息

• Rh(III)-Catalyzed and Solvent-Controlled Chemoselective Synthesis of Chalcone and Benzofuran Frameworks via Synergistic Dual Directing Groups Enabled Regioselective C–H Functionalization: A Combined Experimental and Computational Study
  作者：Wei Yi、Weijie Chen、Fu-Xiaomin Liu、Yuting Zhong、Dan Wu、Zhi Zhou、Hui Gao

  DOI：10.1021/acscatal.8b02402

  日期：2018.10.5

  between the hydroxyl group and the Rh(III) catalyst play a decisive role in promoting the regioselective migratory insertion of the alkyne moiety. Thereafter, two solvent-controlled switchable reaction pathways, which respectively involve tandem β–H elimination/hydrogen transfer/oxidative addition/C–O bond reductive elimination/oxidation (for low-polar solvents: path I–Ia via a RhIII–RhI–RhIII pathway)

  借助协同双指导基团（O–NHAc部分和羟基）辅助策略，有效和实用的Rh（III）催化的区域选择性氧化还原中性C–H功能化了多种N已经实现了具有炔丙醇的β-苯氧基乙酰胺，其导致以溶剂控制的化学选择性方式多样化地合成了优先的苯并呋喃和查尔酮骨架。实验和计算研究表明，双指导基团之间氢键的形成以及随后的羟基与Rh（III）催化剂之间的配位相互作用在促进炔烃部分的区域选择性迁移插入中起决定性作用。此后，二溶剂控制的切换的反应途径，其分别涉及串联β-H消除/氢转移/氧化加成/ C-O键还原消除/氧化（低极性溶剂：路径我-我一个经由铑III -铑我-Rh III途径）和氧化加成/β-H消除/氢转移/质子分解（用于高极性溶剂：路径II - II b经由铑III -Rh V -Rh III途径），后跟提供相应的化学选择性优异的产品。综上所述，我们在此给出的结果不仅扩展了O-NHAc定向的C-H活化的范围，而
• Relay Rhodium(I)/Acid Catalysis for Rapid Access to Benzo‐2 <i>H</i> ‐Pyrans and Benzofurans
  作者：Huilong Zhu、Qianqian Zhou、Na Liu、Junhao Xing、Weijun Yao、Xiaowei Dou

  DOI：10.1002/adsc.202200024

  日期：2022.3.15

  Relay rhodium(I)/Brønsted acid catalysis for tandem arylation−cyclization reaction was developed. Chemodivergent syntheses of benzo-2H-pyrans and benzofurans from propargyl alcohols and ortho-hydroxylated arylboronic acids were achieved under this relay catalysis system. An ortho-hydroxy effect on changing the chemoselectivity and reactivity was observed.

  开发了用于串联芳基化-环化反应的中继铑（I）/布朗斯台德酸催化。在该中继催化体系下，实现了由炔丙基醇和邻羟基化芳基硼酸化学分散合成苯并-2 H-吡喃和苯并呋喃。观察到邻羟基对改变化学选择性和反应性的影响。
• One-Pot Synthesis of Benzofurans via Palladium-Catalyzed Enolate Arylation with <i>o</i>-Bromophenols
  作者：Christian Eidamshaus、Jason D. Burch

  DOI：10.1021/ol801510n

  日期：2008.10.2

  A one-pot synthesis of benzofurans which utilizes a palladium-catalyzed enolate arylation is described. The process demonstrates broad substrate scope and provides differentially substituted benzofurans in moderate to excellent yields. The utility of the method is further demonstrated by the synthesis of the natural product eupomatenoid 6 in three steps.