2-丁基-4-苯基呋喃 | 63591-11-7

• 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-丁基-4-苯基呋喃
• 英文名称: 2-butyl-4-phenylfuran
• 英文别名: 2-Butyl-4-phenylfuran
• CAS: 63591-11-7
• 化学式: C₁₄H₁₆O
• 分子量: 200.28
• InChiKey: GYIXTWHHRVNNPH-UHFFFAOYSA-N

物化性质

• 沸点：
  290.7±19.0 °C(Predicted)
• 密度：
  0.984±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-(hex-1-yn-1-yl)-2-phenyloxirane 在 silver hexafluoroantimonate 、 三苯基膦氯金 、 silver carbonate 作用下， 以 甲苯 为溶剂， 生成 2-丁基-4-苯基呋喃
  参考文献：
  名称：

  Gold-catalyzed Cycloisomerization of 2-Aryl-2-(arylamino)-3-butyn-1-ols toward 2-(2′-Aminoaryl)-2,5-dihydrofurans

  摘要：

  AbstractAn interesting and highly selective gold‐catalyzed cycloisomerization of 2‐aryl‐2‐(arylamino)‐3‐butyn‐1‐ols to afford 2‐(2′‐aminoaryl)‐2,5‐dihydrofurans has been reported. The reaction is atom economic and highly efficient, and tolerates many functional groups including the cyano and allyl groups. A plausible mechanism for this new cycloismerization is also proposed.magnified image

  DOI：

  10.1002/adsc.201701638

文献信息

• Poly(ethylene glycol) as a Reaction Matrix in Platinum- or Gold-Catalyzed Cycloisomerization: A Mechanistic Investigation
  作者：Rosella Spina、Evelina Colacino、Jean Martinez、Frédéric Lamaty

  DOI：10.1002/chem.201203800

  日期：2013.3.18

  Design for diversity: A new catalytic system based on PEG‐3400 and a metal salt (Pt or Au) was designed to efficiently perform a cycloisomerization reaction under microwave irradiation, which gave diverse heterocycles in good to excellent yields, after a precipitation/filtration procedure (see scheme).

  多样性设计：设计了一种基于PEG-3400和金属盐（Pt或Au）的新型催化体系，可以在微波辐射下有效地进行环异构化反应，经过沉淀/过滤后，该杂环化合物可以以优良的产率获得优异的多样化杂环（请参阅方案）。
• A simple and convenient synthesis of substituted furans and pyrroles by CuCl2-catalyzed heterocyclodehydration of 3-yne-1,2-diols and N-Boc- or N-tosyl-1-amino-3-yn-2-ols
  作者：Bartolo Gabriele、Pierluigi Plastina、Mabel V. Vetere、Lucia Veltri、Raffaella Mancuso、Giuseppe Salerno

  DOI：10.1016/j.tetlet.2010.05.001

  日期：2010.7

  A simple and economical synthesis of substituted furans and pyrroles, by ligand-free CuCl2-catalyzed heterocyclodehydration of readily available 3-yne-1,2-diols and N-Boc- or N-tosyl-1-amino-3-yn-2-ols, respectively, is presented. Reactions are carried out in MeOH at 80–100 °C for 1–24 h and afford the corresponding heterocyclic derivatives in 53–99% isolated yields.

  一种简单经济的取代呋喃和吡咯的合成方法，该方法通过无配体的CuCl 2催化的易获得的3-炔-1,2-二醇和N - Boc-或N-甲苯磺酰基-1-氨基-3-yn-的杂环脱水分别给出了2-ols。反应在MeOH中于80-100°C下进行1-24h，并以53-99％的分离产率得到相应的杂环衍生物。
• An efficient furan synthesis using heterogeneous catalysis
  作者：Simon J. Hayes、David W. Knight、Melanie D. Menzies、Mark O’Halloran、Wen-Fei Tan

  DOI：10.1016/j.tetlet.2007.08.102

  日期：2007.10

  A wide variety of 3-alkyne-1,2-diols have been found to undergo exceptionally clean 5-endo-dig cyclisations followed by dehydration at ambient temperature to give the corresponding furans in essentially quantitative yields when exposed to 10 mol % of 10%,w/w silver(1) nitrate absorbed on silica gel. (C) 2007 Elsevier Ltd. All rights reserved.
• Copper-Catalyzed Synthesis of Substituted Furans and Pyrroles by Heterocyclodehydration and Tandem Heterocyclodehydration–Hydration of 3-Yne-1,2-diols and 1-Amino-3-yn-2-ol Derivatives
  作者：Bartolo Gabriele、Lucia Veltri、Pierluigi Plastina、Raffaella Mancuso、Mabel V. Vetere、Vito Maltese

  DOI：10.1021/jo400533j

  日期：2013.5.17

  CuCl2-catalyzed heterocyclodehydration of readily available 3-yne-1,2-diols and 1-amino-3-yn-2-ol derivatives afforded substituted furans and pyrroles, respectively, in good to high yields (53-99%) under mild conditions (MeOH as the solvent, 80-100 degrees C, 1-24 h). In the case of 2,2-dialkynyl-1,2-diols, bearing an additional alkynyl substituent at C-2, a cascade process, corresponding to copper-catalyzed heterocyclodehydration followed by acid-catalyzed hydration of the triple bond, was realized when the reaction was carried out in the presence of both CuCl2 and TsOH, leading to 3-acylfurans in one step and high yields (75-84%). Under the same conditions, N-Boc-2-alkynyl-1-amino-3-yn-2-ols were converted into the corresponding N-unsubstituted 3-acylpyrroles in low to fair yields (19-59%). However, working in the presence of added water and a large excess of CO2 (40 atm), in addition to CuCl2 and TsOH, caused a significant improvement of the yields of 3-acylpyrroles (68-87%), thus making the method of general synthetic applicability.
• Gold-catalyzed Cycloisomerization of 2-Aryl-2-(arylamino)-3-butyn-1-ols toward 2-(2′-Aminoaryl)-2,5-dihydrofurans
  作者：Jianlin Yang、Yuanhua Wu、Ming Zhang、Dunru Zhu、Ruwei Shen

  DOI：10.1002/adsc.201701638

  日期：2018.5.16

  AbstractAn interesting and highly selective gold‐catalyzed cycloisomerization of 2‐aryl‐2‐(arylamino)‐3‐butyn‐1‐ols to afford 2‐(2′‐aminoaryl)‐2,5‐dihydrofurans has been reported. The reaction is atom economic and highly efficient, and tolerates many functional groups including the cyano and allyl groups. A plausible mechanism for this new cycloismerization is also proposed.magnified image