2,3,4,5-四(4-(三氟甲基)苯基)呋喃 | 1025014-21-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,3,4,5-四(4-(三氟甲基)苯基)呋喃
• 英文名称: 2,3,4,5-tetrakis(4-(trifluoromethyl)phenyl)furan
• 英文别名: 2,3,4,5-tetrakis[4-(trifluoromethyl)phenyl]furan；2,3,4,5-tetrakis(4-trifluoromethyl-phenyl)furan
• CAS: 1025014-21-4
• 化学式: C₃₂H₁₆F₁₂O
• 分子量: 644.459
• InChiKey: KFVMZRFUYFHZFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  45
• 可旋转键数：
  4
• 环数：
  5.0
• 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：
  13

反应信息

• 作为产物：
  描述：

  1-(三氟甲基)-4-[2-[4-(三氟甲基)苯基]乙炔基]苯 在 氧气 、 copper diacetate 、 palladium diacetate 、 溶剂黄146 作用下， 100.0 ℃ 、101.0 kPa 条件下， 反应 12.0h， 以96%的产率得到2,3,4,5-四(4-(三氟甲基)苯基)呋喃
  参考文献：
  名称：

  一种简便实用的方法，以大气氧为末端氧化剂，从炔烃中合成多取代基呋喃

  摘要：

  我们在这里介绍一种简便实用的方法，使用大气氧作为末端氧化剂，由乙酸钯与乙酸铜在乙酸中催化的炔烃合成四取代呋喃。各种内部芳烃以令人满意的产率提供了目标呋喃。

  DOI：

  10.1002/cjoc.201400386

文献信息

• Palladium-Catalyzed Oxidation and Cyclization of Carbon-Carbon Triple Bonds in Fluorous Media Using Molecular Oxygen
  作者：Huanfeng Jiang、Yanmei Wen、Shifa Zhu、Azhong Wang、Zhenwang Chen

  DOI：10.1055/s-0030-1259929

  日期：2011.4

  An intriguing, facile, and efficient oxidation and cyclization of alkynes catalyzed by Pd(OAc)2 in a fluorous biphasic system of N,N-dimethylacetamide (DMA) and perfluorodecalin directly with molecular oxygen is described, which opens an efficient access to tetrasubstituted furans. Under the optimized conditions, intermolecular reaction between diverse alkynes provides the corresponding mixture of regioisomers with appreciable selectivity. Intramolecular oxidation and cyclization of alkynes are also successfully demonstrated. The reaction proceeds efficiently under mild conditions with atmospheric oxygen as the sole oxidant.

  本文报道了一种由Pd(OAc)2在N,N-二甲基乙酰胺（DMA）和全氟十烷的氟烥双相体系中直接催化炔烃的氧化环化反应，该反应利用分子氧作为氧化剂，为四取代呋喃的高效合成开辟了新途径。在优化的条件下，不同炔烃之间的分子间反应提供了相应的位置异构体混合物，并具有良好的选择性。炔烃的分子内氧化环化反应也成功实现。该反应在温和条件下高效进行，仅使用大气氧作为唯一的氧化剂。
• Synthesis of Tetrasubstituted Furans via Sequential Pd(OAc)2/Zn(OTf)2-Catalyzed Oxidation and Cyclization of Aromatic Alkynes with Molecular Oxygen
  作者：Huanfeng Jiang、Azhong Wang、Qiuxiang Xu

  DOI：10.1055/s-0028-1088216

  日期：2009.4

  The development of a new method for the synthesis of tetrasubstituted furans using aromatic alkynes is reported. The strategy involves a tandem process of palladium-catalyzed oxidation and Zn(OTf)2-catalyzed cyclization in the presence of molecular oxygen.

  报道了一种利用芳香烷炔合成四取代呋喃的新方法。该策略涉及在分子氧存在下进行的钯催化氧化和Zn(OTf)2催化环化的串联过程。
• Synthesis of cyclopentadienyl alkyl ethers via Pd-catalyzed cyclotrimerization of diarylacetylenes
  作者：Ranran Cai、Mengmeng Huang、Xiuling Cui、Jianye Zhang、Chenxia Du、Yusheng Wu、Yangjie Wu

  DOI：10.1039/c3ra41326h

  日期：——

  A novel efficient tandem cyclization–methoxylation reaction has been developed to synthesize cyclopentadienyl alkyl ethers via palladium-catalyzed trimerization of diarylethynes and elimination of one dimethoxymethyl benzene molecule. The reaction mechanism was investigated by the Q-Tof APCI-HRMS technique, and the fluorescent properties of the obtained compounds were studied in the solid state and in solution.

  开发了一种新型高效串联环化-甲氧基化反应，通过钯催化的二芳基乙炔三聚作用和一分子二甲氧甲基苯的消除，合成环戊二烯基烷基醚。通过Q-Tof APCI-HRMS技术研究了反应机理，并在固态和溶液中研究了所获化合物的荧光性质。
• Site-selective Suzuki–Miyaura cross-coupling reactions of 2,3,4,5-tetrabromofuran
  作者：Munawar Hussain、Rasheed Ahmad Khera、Nguyen Thai Hung、Peter Langer

  DOI：10.1039/c0ob00695e

  日期：——

  Suzuki–Miyaura reactions of 2,3,4,5-tetrabromofuran allow a convenient and site-selective synthesis of mono-, di- and tetraarylfurans which are not readily available by other methods.

  2,3,4,5-四溴呋喃的 Suzuki–Miyaura 反应可以方便地、位点选择性地合成单、二和四芳基呋喃，这是其他方法不易获得的。
• Palladium-Catalyzed Perarylation of 3-Thiophene- and 3-Furancarboxylic Acids Accompanied by C−H Bond Cleavage and Decarboxylation
  作者：Masaya Nakano、Hayato Tsurugi、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/ol800466b

  日期：2008.5.1

  3-Thiophene- and 3-furancarboxylic acids efficiently undergo perarylation accompanied by cleavage of the three C-H bonds and decarboxylation upon treatment with excess aryl bromides in the presence of a palladium catalyst to give the corresponding tetraarylated products in good yields.