bis(4-methoxyphenyl)(5-methyl-2-furyl)methane

• 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: bis(4-methoxyphenyl)(5-methyl-2-furyl)methane
• 英文别名: 2-[bis(4-methoxyphenyl)methyl]-5-methylfuran
• 化学式: C₂₀H₂₀O₃
• 分子量: 308.377
• InChiKey: RKAFYPOJOGZTNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  31.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzyl-3-hydroxy-3-(6-hydroxybenzo[d][1,3]dioxol-5-yl)indolin-2-one 、 bis(4-methoxyphenyl)(5-methyl-2-furyl)methane 在 对甲苯磺酸 作用下， 以 1,2-二氯乙烷 为溶剂， 以81%的产率得到1-benzyl-7'-(bis(4-methoxyphenyl)methylene)-8a'-methyl-5a',6',7',8a'-tetrahydrospiro[indoline-3,9'-[1,3]dioxolo[4,5-g]furo[3,2-b]chromen]-2-one
  参考文献：
  名称：

  含2,5-二烷基呋喃的羟吲哚嵌入式邻苯二甲腈的脱芳香族[4 + 2]环加成反应

  摘要：

  2,5-二烷基呋喃通过有机催化脱芳香性[4 + 2]环加成并掺入羟吲哚嵌入的邻苯二甲酰甲烷，轻松地转变为具有药学意义的螺[chroman-4,3'-oxindole]支架。该方法具有反应条件温和，操作简单，收率高和非对映选择性优良的特点。

  DOI：

  10.1002/adsc.201801509
• 作为产物：
  描述：

  2-甲基呋喃 、 二甲氧基苯甲醇 在 十二烷基苯磺酸 作用下， 以 水 为溶剂， 反应 24.0h， 以94%的产率得到bis(4-methoxyphenyl)(5-methyl-2-furyl)methane
  参考文献：
  名称：

  表面活性剂型布朗斯台德酸催化水中酒精的脱水亲核取代。

  摘要：

  已经开发出使用十二烷基苯磺酸（DBSA）作为水中的表面活性剂型布朗斯台德酸催化剂，用多种以碳原子和杂原子为中心的亲核试剂对苯甲醇进行脱水亲核取代的方案。该反应系统可以应用于水中1-羟基糖的立体选择性C-糖基化。[反应：请参见文字]。

  DOI：

  10.1021/ol062813j

文献信息

• Solvent-free Brønsted acid catalysed alkylation of arenes and heteroarenes with benzylic alcohols
  作者：Margherita Barbero、Silvano Cadamuro、Stefano Dughera、Marta Rucci、Giulia Spano、Paolo Venturello

  DOI：10.1016/j.tet.2014.01.011

  日期：2014.3

  A simple and efficient alkylation of aromatic and heteroaromatic compounds via the direct SN1-type nucleophilic substitution of benzylic alcohols in the presence of catalytic amounts of the strong Brønsted acid o-benzenedisulfonimide under neat conditions is herein reported. A library of di- and triaryl (and heteroaryl) methanes was prepared in good yields and high regioselectivity. The observed reactivity

  本文报道了在纯净条件下，在催化量的强布朗斯台德酸邻苯二磺酰亚胺存在下，通过苄基醇的直接S N 1型亲核取代，对芳香族和杂芳香族化合物进行的简单有效烷基化。以高收率和高区域选择性制备了二芳基和三芳基（和杂芳基）甲烷的库。已证明观察到的反应性与Mayr的亲核性和亲电子性等级相符。
• Synthesis and investigation of catalytic affinities of water-soluble amphiphilic calix[n]arene surfactants in the coupling reaction of some heteroaromatic compounds
  作者：Serkan Sayin、Mustafa Yilmaz

  DOI：10.1016/j.tet.2016.08.066

  日期：2016.10

  their surfactant abilities, and the effects of water amount used and reaction durations on the catalytic activities of these amphiphilic calix[n]arene derivatives were also investigated. Observations indicated that these amphiphilic calix[n]arene catalysts exhibited high catalytic activities in the coupling reactions of 2-methylfuran and N-methylindole with some alcohols in water.

  通过引入磺酸基，成功合成了六种具有两亲性的杯芳烃[ n ]芳烃基布朗斯台德酸型催化剂。使用FTIR，1 H NMR，13 C NMR，APT-NMR和元素分析技术对它们的结构进行表征。此外，在2-甲基呋喃和/或N-甲基吲哚与某些仲醇在水性介质中的偶联反应中评估了它们的催化能力。还研究了它们的表面活性剂能力，水用量和反应时间对这些两亲杯芳烃[ n ]芳烃衍生物的催化活性的影响。观察表明，这些两亲杯[在2-甲基呋喃和N-甲基吲哚与某些醇在水中的偶联反应中，n ]芳烃催化剂表现出高催化活性。
• Kinetics of the Friedel−Crafts Alkylations of Heterocyclic Arenes:  Comparison of the Nucleophilic Reactivities of Aromatic and Nonaromatic π-Systems
  作者：Matthias F. Gotta、Herbert Mayr

  DOI：10.1021/jo981373+

  日期：1998.12.1

  The kinetics of the reactions of benzhydryl cations with heteroarenes (N-methylpyrrole, furan, 2-methylfuran? and 2-methylthiophene) have been determined photometrically in dichloromethane, and the reaction products have been completely characterized by H-1 and C-13 NMR spectroscopy. The reactions follow second-order kinetics with rate-limiting formation of the sigma-adducts. The second-order rate constants correlate linearly with the electrophilicity parameter E of the benzhydryl cations. This allows the determination of the reactivity parameters N and s for the heteroarenes according to the linear free enthalpy relationship log k = s(E + N) (Mayr, H.; Patz, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 938-957). The nucleophilicity parameters N thus defined allow a direct comparison of the nucleophilic reactivities of aromatic and nonaromatic :pi-systems. Since N correlates linearly with sigma(arene)(+), it becomes possible to derive N parameters for arenes and heteroarenes with known sigma(+) parameters and to calculate absolute rate constants for their reactions with carbenium ions and diazonium ions. Applications of the reactivity parameters thus determined for the quantitative and qualitative prediction of the rates of electrophilic aromatic substitutions are discussed.
• Electrophilic Alkylations in Neutral Aqueous or Alcoholic Solutions
  作者：Matthias Hofmann、Nathalie Hampel、Tanja Kanzian、Herbert Mayr

  DOI：10.1002/anie.200460812

  日期：2004.10.11
• Brønsted acidic magnetic nano-Fe3O4-adorned calix[n]arene sulfonic acids: synthesis and application in the nucleophilic substitution of alcohols
  作者：Serkan Sayin、Mustafa Yilmaz

  DOI：10.1016/j.tet.2014.06.034

  日期：2014.9

  Three magnetically recoverable Bronsted acidic calix[n]arene derivatives were successfully constructed by immobilizing calix[n]arene sulfonic acids onto silica-coated magnetic nanoparticles, a process, which allows calix[n]arene derivatives to acquire magnetic properties. All of the magnetically recoverable Bronsted acidic calix[n]arenes efficiently catalyze the coupling of electron-rich arenes with some alcohols in water. After separation and recovery from the reaction mixture by a simple magnet, these Bronsted acidic calix[n]arenes can be recycled many times without losing their catalytic activity. (C) 2014 Elsevier Ltd. All rights reserved.