2-methyl-5-(1-(5-methylfuran-2-yl)pentyl)furan | 94163-05-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-methyl-5-(1-(5-methylfuran-2-yl)pentyl)furan
• 英文别名: 1,1-bis(5-methyl-2-furyl)pentane；1,1-bis[5-methyl-2-furyl]pentane；5,5'-dimethyl-2,2'-pentane-1,1-diyl-bis-furan；1,1-Bis-<5-methyl-furyl-(2)>-pentan；2-Methyl-5-[1-(5-methylfuran-2-yl)pentyl]furan；2-methyl-5-[1-(5-methylfuran-2-yl)pentyl]furan
• CAS: 94163-05-0
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: MTWWORXCHQRRII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(5-methylfuran-2-yl)pentan-1-ol 在 ytterbium(III) triflate 作用下， 以 硝基甲烷 为溶剂， 反应 0.17h， 以64%的产率得到2-methyl-5-(1-(5-methylfuran-2-yl)pentyl)furan
  参考文献：
  名称：

  二-和triheteroarylalkanes通过自缩合和分子内的杂芳基醇的弗里德尔-克拉夫茨型反应†

  摘要：

  通过Yb（III）催化2-糠基（或2-噻吩基或3-吲哚基）醇的顺序自缩合反应，然后进行分子内Friedel-Crafts型反应，开发了一种有效的合成方法，用于二杂芳基甲烷和1,3-二杂芳基丙烯。消除醛。该方法为传统的二杂芳基烷烃的合成提供了有力的途径和潜在的替代方法，后者是几种有趣的杂芳基化合物的合成的前体，更重要的是生物燃料的合成。

  DOI：

  10.1039/c3ob41945b

文献信息

• 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
• Synthesis of furan derivatives via cascade-type reactions catalyzed by solid acids
  作者：Marvin H. Chávez-Sifontes、Marcelo E. Domine、Susana Valencia

  DOI：10.1016/j.cattod.2015.04.018

  日期：2015.11

  The 2-methylfuran (2-MF), easily obtained from furfural as a lignocellulosic biomass derivative, can be converted in good yields (70%) into 5,5-bis(5-methyl-2-furyl)pentan-2-one by condensation in the presence of mineral acids. This molecule is an important precursor for various interesting industrial products, such as benzofuranics with physiological activity and hydrocarbon mixtures useful as fuel components. In this work, the synthesis of 5,5-bis(5-methyl-2-furyl)pentan-2-one was successfully achieved (yield = 80%) via hydrolysis/condensation of 2-methylfuran, by using ethanol/water as solvent and Amberlyst (R) as a solid catalyst under moderate reaction conditions. Different polymeric ionic exchange resins were tested, conversion of 2-MF and product performances during reaction showed a proportional dependence to the capacity of proton exchange of resins. Amberlyst 15 presented the best results, and the resin can be regenerated and reused several times arriving to a constant product yield after the 3rd-4th reuse. Results attained for different zeolites tested indicate that 2-MF conversion appears to be function of pore size and channels structure of zeolite. These catalysts produced low yields of desired product mainly due to deactivation by the retention of intermediate reactions and products on the surface and inside pores. The use of H-Beta (F-) catalyst presenting a more hydrophobic surface could partially minimize catalytic deactivation. (C) 2015 Elsevier B.V. All rights reserved.
• Di- and triheteroarylalkanes via self-condensation and intramolecular Friedel–Crafts type reaction of heteroaryl alcohols
  作者：Seema Dhiman、S. S. V. Ramasastry

  DOI：10.1039/c3ob41945b

  日期：——

  diheteroarylmethanes and 1,3-diheteroarylpropenes has been developed via Yb(III)-catalyzed sequential self-condensation of 2-furfuryl (or 2-thienyl or 3-indolyl) alcohols followed by intramolecular Friedel–Crafts type reaction and elimination of an aldehyde. This method offers a powerful entry and a potential alternative to the traditional synthesis of diheteroarylalkanes, which are precursors to the synthesis

  通过Yb（III）催化2-糠基（或2-噻吩基或3-吲哚基）醇的顺序自缩合反应，然后进行分子内Friedel-Crafts型反应，开发了一种有效的合成方法，用于二杂芳基甲烷和1,3-二杂芳基丙烯。消除醛。该方法为传统的二杂芳基烷烃的合成提供了有力的途径和潜在的替代方法，后者是几种有趣的杂芳基化合物的合成的前体，更重要的是生物燃料的合成。