2-(4-methoxyphenyl)-3-phenylbenzo[b]furan | 16762-21-3

• 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: 2-(4-methoxyphenyl)-3-phenylbenzo[b]furan
• 英文别名: 2-(4-methoxy-phenyl)-3-phenyl-benzofuran；5-Methyl-3-phenyl-2-p-anisyl-benzofuran；2-(4-Methoxyphenyl)-3-phenylbenzofuran；2-(4-methoxyphenyl)-3-phenyl-1-benzofuran
• CAS: 16762-21-3
• 化学式: C₂₁H₁₆O₂
• 分子量: 300.357
• InChiKey: XEMFUPSMXJSZCF-UHFFFAOYSA-N

物化性质

• 熔点：
  145-147 °C(Solv: benzene (71-43-2); ligroine (8032-32-4))
• 沸点：
  429.3±40.0 °C(Predicted)
• 密度：
  1.151±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯甲醚 在 palladium diacetate 、 磷酸 、 caesium carbonate 、 三苯基膦 、 三氟乙酸酐 作用下， 以 水 、 xylene 为溶剂， 反应 8.02h， 生成 2-(4-methoxyphenyl)-3-phenylbenzo[b]furan
  参考文献：
  名称：

  A high speed parallel synthesis of 1,2-diaryl-1-ethanones via a clean-chemistry C–C bond formation reaction

  摘要：

  In this report, we describe the parallel as well as conventional synthesis of 1,2-diaryl-1-ethanones via environmentally benign acylation of arenes with in situ generated arylacetyl trifluoroacetates. A wide variety of arylacetic acids I participated in trifluoroacetic anhydride/ phosphoric acid mediated C-C bond formation reaction when reacted with arenes of type II to give 1,2-diaryl-1-ethanones III in good to excellent yield. Under the solvent-free conditions these chemical transformations that normally require longer reaction time can be performed within minutes in good yield. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00407-1

文献信息

• Palladium-catalyzed synthesis of benzofurans via C–H activation/oxidation tandem reaction and its application to the synthesis of decursivine and serotobenine
  作者：Lei Guo、Fengying Zhang、Weimin Hu、Lei Li、Yanxing Jia

  DOI：10.1039/c3cc49717h

  日期：——

  A new palladium-catalyzed method for the synthesis of benzofurans by reaction of 2-hydroxystyrenes and iodobenzenes via a C–H activation/oxidation tandem reaction has been unprecedentedly discovered. By using this strategy, the overall synthetic efficiency of the synthesis of decursivine and its analogues was indeed improved. Preliminary mechanistic studies shed light into the possible mechanisms.

  一种通过C-H活化/氧化串联反应，以钯为催化剂，由2-羟基苯乙烯和碘苯合成苯并呋喃的新方法被前所未有的发现了。运用该策略，合成化合物细辛碱及其类似物的整体效率确实得到了提高。初步的机理研究表明了可能的反应机理。
• Palladium-Catalyzed Cross-Coupling of Benzyl Ketones and<i>α,β</i>-Unsaturated Carbonyl and Phenolic Compounds with<i>o</i>-Dibromobenzenes to Produce Cyclic Products
  作者：Yoshito Terao、Tetsuya Satoh、Masahiro Miura、Masakatsu Nomura

  DOI：10.1246/bcsj.72.2345

  日期：1999.10

  A number of carbonyl and phenolic compounds efficiently couple with o-dibromobenzenes in the presence of a palladium catalyst and a base to give the corresponding oxygen-containing heterocycles or carbocyclic compounds. Thus, from the reactions of benzyl phenyl ketones, 1-naphthols, and α,β-unsaturated aldehydes and ketones, benzofuran, benzopyran, benzocyclobutane, and indene derivatives, respectively, are produced selectively via the successive formation of C–C and C–O bonds or of two C–C bonds.

  一些羰基和酚类化合物在钯催化剂和碱的存在下与邻二溴苯有效耦合，生成相应的含氧杂环或碳环化合物。因此，通过苄基酮、1-萘醇以及α,β-不饱和醛和酮的反应，选择性地生成苯并呋喃、苯并吡喃、苯并环丁烷和茚衍生物，这些化合物是通过C–C键和C–O键的连续形成或两个C–C键的形成得到的。
• Nickel-Catalyzed Ring-Opening of Benzofurans for the Divergent Synthesis of <i>ortho</i>-Functionalized Phenol Derivatives
  作者：Changhui Lu、Yueping Lin、Minyan Wang、Jiaming Zhou、Shuo Wang、Huanfeng Jiang、Kai Kang、Liangbin Huang

  DOI：10.1021/acscatal.2c04442

  日期：2023.2.17

  The ring-opening reaction of benzofuran is a highly desirable, yet underdeveloped transformation for the construction of valuable phenol derivatives. Herein, we report a nickel-catalyzed ring-opening transformation of benzofuran with silanes, giving ortho-alkene-, branched/linear alkyl silane-, and alkenyl silane-substituted phenol derivatives selectively. Control experiments and DFT calculations supported

  苯并呋喃的开环反应是一种非常理想但尚未开发的转化，用于构建有价值的苯酚衍生物。在此，我们报道了镍催化的苯并呋喃与硅烷的开环转化，选择性地得到邻-烯烃-、支链/直链烷基硅烷-和烯基硅烷-取代的苯酚衍生物。对照实验和 DFT 计算支持 Ni-H 插入和 β-O 消除以实现苯并呋喃的正式 C-O 键活化，而不是通过将镍 (0) 直接氧化加成到苯并呋喃的 C-O 键中。通过 Ni(I)–H 或 Ni(I)–[Si] 中间体发生进一步的区域选择性氢化硅烷化或脱氢硅烷化，形成邻位-支链/直链烷基硅烷或烯基硅烷取代的苯酚衍生物。