3,4-Dimethyl-2,5-diphenylfuran | 51181-43-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 3,4-Dimethyl-2,5-diphenylfuran
• 英文别名: 3,4-Dimethyl-2,5-diphenyl-furan
• CAS: 51181-43-2
• 化学式: C₁₈H₁₆O
• 分子量: 248.324
• InChiKey: QIVGWOACDBZFEX-UHFFFAOYSA-N

物化性质

• 熔点：
  116 °C
• 沸点：
  326.5±11.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  3,4-Dimethyl-2,5-diphenylfuran 在 硝酸 、 丙酸 作用下， 生成 cis-Dibenzoyl-2.3 buten-2
  参考文献：
  名称：

  Some Substituted 2,5-Dimesitylfurans

  摘要：

  DOI：

  10.1021/ja01863a055
• 作为产物：
  描述：

  d,l-2,3-Dideuterio-2,3-dimethyl-1,4-diphenyl-1,4-butanedione 在 盐酸 作用下， 以 甲醇 、 氯仿 为溶剂， 生成 3,4-Dimethyl-2,5-diphenylfuran
  参考文献：
  名称：

  Intermediates in the Paal-Knorr Synthesis of Furans

  摘要：

  New experimental evidence for the mechanism of the Paal-Knorr reaction involving the acid-catalyzed cyclization of a 1,4-diketone to form a furan is reported. In aqueous or alcoholic solutions containing hydrochloric acid and in chloroform containing boron trifluoride-etherate d,l- and meso-3,4-diethyl-2,5-hexanediones (2r and 2m) cyclize at unequal rates; the stereochemical configuration of the unchanged done is preserved during the reaction. This disagrees with the commonly accepted mechanism involving the ring closure of the rapidly formed monoenol (11b) followed by loss of water. A pathway involving the rapid protonation of one of the carbonyls followed by the electrophilic attack on the protonated carbonyl by the enol being formed at the other carbonyl group (10c) is proposed to account for the difference in reaction rates between the diastereomers of 3,4-disubstituted 2,5-hexanediones (1-3). The following results also seem to support the intermediacy of 10c. The presence of two isopropyl groups in 3,4-diisopropyl-2,5-hexanedione (3) considerably reduces the rate of cyclization, The catalytic constants k(H)(+) for the cyclization of 2r and 2m are larger than the constants for enolization of methyl ketones. The diastereomers of 2,3-dimethyl-and 2,3-diethyl-1,4-diphenyl-1,4-butanediones (4 and 5), which could enolize only toward the center of the molecule, also react at different rates. The d,l and meso dideuterio analogs (d(2)-4r and d(2)-4m) exhibit a primary isotope effect during cyclization. The order of cyclization of 1,4-diphenyl-1,4-butanedione (6) and its analogs (7-9) reveals that the presence of electron-donating groups facilitate the reaction.

  DOI：

  10.1021/jo00107a006

文献信息

• Ionic Liquid as Catalyst and Reaction Medium: A Simple and Efficient Procedure for Paal–Knorr Furan Synthesis
  作者：Gangqiang Wang、Zhi Guan、Rongchang Tang、Yanhong He

  DOI：10.1080/00397910902978049

  日期：2010.1.14

  The ionic liquid 1-butyl-3-methyl-imidazolium hydrogen sulfate, [bmim]HSO4, efficiently catalyzes Paal–Knorr furan synthesis without any organic solvent. A wide range of aliphatic and aromatic 1,4-diketones easily undergo condensations to form furan derivatives, providing a general and convenient procedure. The Paal–Knorr reaction of ester-substituted 1,4-diketones is first reported. The ionic liquid

  离子液体 1-丁基-3-甲基-咪唑硫酸氢盐 [bmim]HSO4 无需任何有机溶剂即可有效催化 Paal-Knorr 呋喃合成。广泛的脂肪族和芳香族 1,4-二酮很容易缩合形成呋喃衍生物，提供了一个通用和方便的程序。首次报道了酯取代的 1,4-二酮的 Paal-Knorr 反应。离子液体可以回收并重新用于后续运行，而不会显着降低效率。
• Preparations of Furans from<b><i>α</i></b>-Bromo Ketones and Enol Ethers Catalyzed by a Rhenium(I) Nitrogen Complex
  作者：Yuji Koga、Hiroyuki Kusama、Koichi Narasaka

  DOI：10.1246/bcsj.71.475

  日期：1998.2

  By the catalytic use of a rhenium(I) nitrogen complex, [ReCl(N2)(PMe2Ph)4], α-keto radicals are generated from α-bromo ketones and react with vinyl ethers and silyl enol ethers intermolecularly. Various substituted furans, including tetrasubstituted furans such as furoguaiacin, are prepared by this method.

  通过铼(I)氮络合物[ReCl(N2)(PMe2Ph)4]的催化使用，α-酮基由α-溴酮生成，并与乙烯基醚和甲硅烷基烯醇醚发生分子间反应。各种取代的呋喃，包括四取代的呋喃，如呋喃愈创木酚，都是通过这种方法制备的。
• Preparations and Reactions with Amines of Some 1,2-Dibenzoylalkenes¹
  作者：PHILIP S. BAILEY、SHEAFFERS S. BATH、WILLIAM F. THOMSEN、HERBERT H. NELSON、ELIAS E. KAWAS

  DOI：10.1021/jo01109a011

  日期：1956.3
• THE ACTION OF HYDROGEN BROMIDE IN ACETIC ACID ON UNSATURATED 1,4-DIKETONES
  作者：MONROE COUPER、ROBERT E. LUTZ

  DOI：10.1021/jo01195a012

  日期：1942.1
• Studies on Unsaturated 1,4-Dicarbonyl Compounds. IX. Aryl Unsaturated 1,4-Diketones and Ketonic Acids Derived from Dimethyl Maleic and Fumaric Acids
  作者：Robert E. Lutz、Robert J. Taylor

  DOI：10.1021/ja01331a045

  日期：1933.4