2,5-diphenylbenzofuran | 121045-39-4

• 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: 2,5-diphenylbenzofuran
• 英文别名: 2,5-diphenyl-1-benzofuran
• CAS: 121045-39-4
• 化学式: C₂₀H₁₄O
• 分子量: 270.331
• InChiKey: MLIJBAPZZAYMJC-UHFFFAOYSA-N

物化性质

• 熔点：
  162-164 °C
• 沸点：
  446.8±14.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  21
• 可旋转键数：
  2
• 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：

  2,5-diphenylbenzofuran 在 氧气 、 nitrosonium tetrafluoroborate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以50%的产率得到2,2',5,5'-tetraphenyl-3,3'-bibenzofuran
  参考文献：
  名称：

  Aerobic, Metal-Free, and Catalytic Dehydrogenative Coupling of Heterocycles: En Route to Hedgehog Signaling Pathway Inhibitors

  摘要：

  The nitrosonium ion-catalyzed dehydrogenative coupling of heteroarenes under mild reaction conditions is reported. The developed method utilizes ambient molecular oxygen as a terminal oxidant, and only water is produced as byproduct. Dehydrogenative coupling of heteroarenes translated into the rapid discovery of novel hedgehog signaling pathway inhibitors, emphasizing the importance of the developed methodology.

  DOI：

  10.1021/acs.orglett.8b00521
• 作为产物：
  描述：

  5-phenylbenzofuran 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 2,5-diphenylbenzofuran
  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

• Linear Polystyrene-Stabilized Palladium Nanoparticles-Catalyzed C–C Coupling Reaction in Water
  作者：Atsushi Ohtaka、Takuto Teratani、Ryohei Fujii、Kanako Ikeshita、Takahiro Kawashima、Koichi Tatsumi、Osamu Shimomura、Ryôki Nomura

  DOI：10.1021/jo200485q

  日期：2011.5.20

  Linear polystyrene-stabilized PdO nanoparticles (PS-PdONPs) were prepared in water by thermal decomposition of Pd(OAc)2 in the presence of polystyrene. The immobilization degree of palladium was dependent on the molecular weight of polystyrene, while the size of the Pd nanoparticles was not. Linear polystyrene-stabilized Pd nanoparticles (PS-PdNPs) were also prepared using NaBH4 and phenylboronic acid

  线性聚苯乙烯稳定的PdO纳米颗粒（PS-PdONPs）在水中通过在聚苯乙烯存在下热分解Pd（OAc）2制备。钯的固定度取决于聚苯乙烯的分子量，而钯纳米粒子的大小则不然。还使用NaBH 4和苯基硼酸作为还原剂制备了线性聚苯乙烯稳定的Pd纳米颗粒（PS-PdNPs）。PS-PdONPs在水中的Suzuki偶联反应的催化活性略高于PS-PdNPs。PS-PdONP在水中显示出对铃木和无铜Sonogashira偶联反应的高催化活性，可循环使用而不会损失活性。
• Microwave-assisted efficient synthesis of 2-arylbenzo[b]furans and 2-ferrocenylbenzo[b]furans from readily prepared propargylic alcohols and o-iodophenols
  作者：LIANSHENG WU、XIAOKANG SHI、XIAOYUN XU、FEN LIANG、GUOSHENG HUANG

  DOI：10.1007/s12039-011-0137-9

  日期：2011.9

  one-pot with iodobenzene, 2-methyl-3-butyn-2-ol and 2-iodo-4-methylphenol as reactants. A simple and efficient method for synthesis of 2-arylbenzo[b]furnas and 2-ferrocenylbenzo[b]furans has been developed from the Sonogashira coupling/cyclization reaction of propargylic alcohols and o-iodophenols in the presence of silica gel and catalytic amounts of PdCl2(PPh3)2 (2 mol%) and CuI (2 mol%) under microwave

  一种简单，高效，快速的方法，由PdCl 2（PPh 3）2（2 ）（2 ）（2 ）（2 ）（2 ）（2 ）（2 ）的催化剂由易于制备的炔丙醇，邻碘苯酚和硅胶合成2-芳基苯并[b]呋喃和2-二茂铁苯并[b]呋喃摩尔％）/ CuI（2摩尔％）和微波促进的Sonogashira偶联/环化反应得以发展。该方法可以产生良好到极好的产量。另外，该方法也可以以碘苯，2-甲基-3-丁炔-2-醇和2-碘-4-甲基苯酚为反应物，一锅法完成。 在硅胶存在下，催化量的炔丙基醇和邻碘苯酚的Sonogashira偶联/环化反应，已经开发出一种简单而有效的合成2-芳基苯并[b]呋喃酮和2-二茂铁基苯并[b]呋喃的方法。在微波条件下，PdCl 2（PPh 3）2（2 mol％）和CuI（2 mol％）。
• Palladium-Catalyzed Regioselective C-2 Arylation of Benzofurans with <i>N′</i> -Acyl Arylhydrazines
  作者：Jun Cao、Zi-Li Chen、Shu-Min Li、Gao-Feng Zhu、Yuan-Yong Yang、Cong Wang、Wen-Zhang Chen、Jian-Ta Wang、Ji-Quan Zhang、Lei Tang

  DOI：10.1002/ejoc.201800374

  日期：2018.6.15

  An efficient and ligand‐free palladium‐catalyzed arylation of benzofurans has been developed with N′ ‐acyl arylhydrazines as the coupling partners. This protocol features a wide functional‐group tolerance and highly regioselective products.

  已开发出一种高效且无配体的钯催化苯并呋喃芳基化反应，以 N'-酰基芳基肼作为偶联伙伴。该协议具有广泛的官能团耐受性和高度区域选择性的产品。
• Pd-Catalyzed Tandem Chemoselective Synthesis of 2-Arylbenzofurans using Threefold Arylating Triarylbismuth Reagents
  作者：Maddali L. N. Rao、Deepak N. Jadhav、Priyabrata Dasgupta

  DOI：10.1002/ejoc.201201314

  日期：2013.2

  A tandem chemoselective synthesis of 2-arylbenzofurans was accomplished from o-hydroxy-gem-(dibromovinyl)benzenes and BiAr3 reagents under palladium-catalyzed conditions. This unique and synthetically valuable strategy proceeds through three consecutive coupling reactions involving triarylbismuth reagents and provides 2-arylbenzofuran products in high yields.

  2-芳基苯并呋喃的串联化学选择性合成是在钯催化条件下由邻羟基宝石-(二溴乙烯基)苯和BiAr3试剂完成的。这种独特且具有合成价值的策略通过涉及三芳基铋试剂的三个连续偶联反应进行，并以高产率提供 2-芳基苯并呋喃产品。
• A Simple and Efficient One-Pot Synthesis of Substituted Benzo[b]furans by Sonogashira Coupling-5-endo-dig Cyclization Catalyzed by Palladium Nanoparticles in Water Under Ligand- and Copper-Free Aerobic Conditions
  作者：Debasree Saha、Raju Dey、Brindaban C. Ranu

  DOI：10.1002/ejoc.201000980

  日期：2010.11

  the synthesis of 2-substituted benzo[b]furan derivatives has been developed by the reaction of 2-iodophenols and arylacetylenes in water catalyzed by palladium nanoparticles generated in situ in open air. The reaction does not require any additive, ligand, or co-catalyst. The reaction occurs through Sonogashira coupling of 2-iodophenols with phenylacetylenes followed by 5-endo-dig cyclization. A series

  通过在露天原位生成的钯纳米颗粒催化 2-碘苯酚和芳基乙炔在水中的反应，开发了一种简单有效的合成 2-取代苯并 [b] 呋喃衍生物的方法。该反应不需要任何添加剂、配体或助催化剂。该反应通过 2-碘苯酚与苯乙炔的 Sonogashira 偶联，然后进行 5-endo-dig 环化而发生。通过该程序以高产率获得了一系列官能化的苯并[b]呋喃衍生物。