(4-Chlorophenyl)-bis-(5-methyl-2-furyl)methane | 86694-53-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4-Chlorophenyl)-bis-(5-methyl-2-furyl)methane
• 英文别名: 5,5'-((4-chlorophenyl)methylene)bis(2-methylfuran)；2,2'-[(4-Chlorophenyl)methylene]bis(5-methylfuran)；2-[(4-chlorophenyl)-(5-methylfuran-2-yl)methyl]-5-methylfuran
• CAS: 86694-53-3
• 化学式: C₁₇H₁₅ClO₂
• 分子量: 286.758
• InChiKey: WHNLHDBHQYRNGR-UHFFFAOYSA-N

物化性质

• 熔点：
  95-100 °C
• 沸点：
  324.5±37.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4-Chlorophenyl)-bis-(5-methyl-2-furyl)methane 在 triphenylmethyl perchlorate 作用下， 以 二氯甲烷 为溶剂， 以53%的产率得到C₁₇H₁₄ClO₂⁽¹⁺⁾*ClO₄^(1-)
  参考文献：
  名称：

  Polyfuryl(aryl)alkanes and their derivatives. 5. Cations and radicals in the polyfuryl(aryl)methane series

  摘要：

  DOI：

  10.1007/bf00531502
• 作为产物：
  描述：

  N-(4-氯苯亚甲基)-4-甲苯磺酰胺 在 [Ir(COD)(SnCl3)Cl(μ-Cl)]2 、 C₁₆H₂₇Br₁₀Ir₂Sn₂ 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.42h， 生成 (4-Chlorophenyl)-bis-(5-methyl-2-furyl)methane
  参考文献：
  名称：

  Heterobimetallic Ir–Sn catalysis: aza-Friedel–Crafts reaction of N-sulfonyl aldimines

  摘要：

  The heterobimetallic complex [Ir(COD)(SnCl3)Cl(mu-Cl)](2) catalyzes the aza-Friedel Crafts reaction of 1,3,5-trimethoxybenzene, as well as substituted indoles with N-sulfonyl aldimines leading to the formation of diarylamines and triarylmethanes in good yields. The symmetrical triarylmethanes were also obtained from diarylamines and suitable nucleophiles via simultaneous cleavage of sp(3) C-N bond and elimination of 1,3,5-trimethoxybenzene. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.074

文献信息

• An Unexpected C–C Bond Cleavage of Acetophenones: Synthesis of Bis(heteroaryl)arylmethanes and Triarylmethanes via SeO2/Lanthanide Chloride Catalyzed Friedel–Crafts Arylation
  作者：H. Meshram、G. Kumar、A. Kumar、A. Swetha、B. Babu

  DOI：10.1055/s-0035-1560808

  日期：——

  A novel synthesis of bisheteroarylaryl methanes and triarylmethanes is described by the selective C–C bond cleavage of acetophenones in the presence of SeO2/lanthanide chlorides. The present strategy provides an in situ generation of aldehydes from acetophenones followed by a double Friedel–Crafts reaction of electron-rich arenes. Natural product 1,1,1-tris(3-indolyl)methane is synthesized in a single

  通过在 SeO2/镧系元素氯化物存在下苯乙酮的选择性 C-C 键断裂描述了双杂芳基芳基甲烷和三芳基甲烷的新合成。本策略提供了从苯乙酮原位生成醛，然后是富电子芳烃的双弗里德尔-克拉夫茨反应。天然产物 1,1,1-三（3-吲哚基）甲烷是按照相同的协议一步合成的。
• Sulfonated Tetraphenylethylene-Based Hypercrosslinked Polymer as a Heterogeneous Catalyst for the Synthesis of Symmetrical Triarylmethanes via a Dual C–C Bond-Cleaving Path
  作者：Gitumoni Kalita、Namrata Deka、Dipankar Paul、Gitish K. Dutta、Paresh Nath Chatterjee、Loknath Thapa

  DOI：10.1055/a-1277-3995

  日期：2021.2

  A sulfonic acid functionalized tetraphenylethylene-based hypercrosslinked polymer (THP-SO3H) with a well-developed porous network and accessible sulfonic acid sites was synthesized and characterized by different analytical techniques. The catalytic prowess of the synthesized material THP-SO3H was investigated in a challenging dual C–C bond-breaking reaction for the synthesis of symmetrical triarylmethanes (TRAMs) in high yield. The scope of the developed metal-free method was also explored with a wide variety of substrates. The organocatalyst can be easily recovered by filtration and reused up to five consecutive cycles without substantial loss in its catalytic efficacy.

  标题：摘要 一种含磺酸基团的四苯基乙烯基高交联聚合物（THP-SO3H）具有良好发达的多孔网络和可访问的磺酸基团，通过不同的分析技术合成并表征。合成材料THP-SO3H的催化能力在一种具有挑战性的双C-C键断裂反应中得到研究，用于合成高收率的对称三芳基甲烷（TRAMs）。还探索了开发的无金属方法在各种底物上的适用范围。这种有机催化剂可以通过过滤轻松回收并在五个连续循环中重复使用，而其催化效能几乎没有明显损失。
• SnCl2 insertion into Ir–Cl and Rh–Cl bonds: Synthesis, characterization and catalytic activity of three-legged piano-stool trichlorostannyl iridium and rhodium complexes
  作者：Arnab Kumar Maity、Manish Bhattacharjee、Sujit Roy

  DOI：10.1016/j.jorganchem.2014.06.011

  日期：2014.10

  [Cp*Ir(SnCl3)2SnCl2(H2O)2}] (1) and [Cp*Ir(SnCl3)3][NH3tBu] (3), respectively. Similarities in NMR data for complexes 1 and 3 suggested that complex 1 converts to anionic [Cp*Ir(SnCl3)3] species in solution via rapid chloride exchange. Similarly, insertion reaction of SnCl2 with [Cp*Ir(PPh3)Cl2] and [Cp*Rh(PPh3)Cl2] afforded single insertion complex [Cp*Ir(PPh3)(SnCl3)Cl] (2) and double insertion complex [

  SnCl 2跨Ir（III）和Rh（III）的五甲基环戊二烯基配合物的轻松插入反应导致Ir-SnCl 3和Rh-SnCl 3异双金属配合物的形成。用[Cp * IrCl 2 ] 2和[Cp * Ir（NH 2 t Bu）Cl 2 ]处理SnCl 2得到[Cp * Ir（SnCl 3）2 SnCl 2（H 2 O）2 }]（1）和[Cp * Ir（SnCl 3）3 ] [NH 3 t Bu]（3）， 分别。相似性为络合物的NMR数据1和3表明复杂1个转换到阴离子的[Cp *的Ir（的SnCl 3）3 ]在经过氯快速交换溶液的种类。同样，SnCl 2与[Cp * Ir（PPh 3）Cl 2 ]和[Cp * Rh（PPh 3）Cl 2 ]的插入反应得到单插入配合物[Cp * Ir（PPh 3）（SnCl 3）Cl]（2）和双插入复合物[Cp * Rh（PPh 3）（SnCl 3）2 ]（4），
• Green synthesis and anti-inflammatory studies of a series of 1,1-bis(heteroaryl)alkane derivatives
  作者：Jaray Jaratjaroonphong、Surisa Tuengpanya、Rungnapha Saeeng、Sarinporn Udompong、Klaokwan Srisook

  DOI：10.1016/j.ejmech.2014.06.045

  日期：2014.8

  an efficient catalyst for a double Friedel–Crafts reaction of various heteroarenes, i.e. 2-methylfuran, 2-ethylfuran, 2-methylthiophene, pyrrole, N-methylpyrrole and indole, using aldehydes as alkylating agents under “open-flask” conditions with toluene or water as the reaction media. In the presence of 10 mol% iodine in toluene at room temperature, both aliphatic and aromatic aldehydes reacted smoothly

  分子碘已被用作各种杂芳烃（例如2-甲基呋喃，2-乙基呋喃，2-甲基噻吩，吡咯，N-甲基吡咯和吲哚，在“开瓶”条件下使用醛作为烷基化剂，并以甲苯或水为反应介质。在室温下，在甲苯中存在10 mol％碘的情况下，脂族醛和芳族醛均能平稳反应，从而以良好或优异的收率得到相应的双（杂芳基）烷烃。有趣的是，以水为溶剂，以中等至良好的产率获得了双（杂芳基）烷烃加合物。本步骤的优点是在一步合成中使用温和的反应条件，催化剂用量低和环境友好的试剂。为了发现新型的非甾体抗炎药，评估了合成的双（杂芳基）烷烃在脂多糖（LPS）刺激的RAW 264.7巨噬细胞模型中的抗炎活性。这些化合物（50μM）显着抑制NO的产生，并且对巨噬细胞没有明显的细胞毒性作用。其中，双[（5-甲基）2-呋喃基]（4-硝基苯基）甲烷对IC的NO抑制作用最强50值42.4±1.9，与阳性对照氨基胍（43.3±2.5μM）相似。因此，双[（5-甲
• Preparation of Triaryl- and Triheteroarylmethanes under Ytterbium Triflate Catalysis and Solvent-Free Conditions
  作者：Salvatore Genovese、Francesco Epifano、Caroline Pelucchini、Massimo Curini

  DOI：10.1002/ejoc.200801115

  日期：2009.3

  Triaryl- and triheteroarylmethanes have been synthesized in very good yield under solvent-free conditions from differently substituted aldehydes and 2-methylfuran or methoxybenzene in the presence of Yb(OTf)3 as catalyst. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  在无溶剂条件下，在 Yb(OTf)3 作为催化剂的存在下，由不同取代的醛和 2-甲基呋喃或甲氧基苯以非常好的收率合成了三芳基甲烷和三杂芳基甲烷。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)