benzyl diphenylmethyl ether | 26059-49-4

• 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: benzyl diphenylmethyl ether
• 英文别名: ((benzyloxy)methylene)dibenzene；(benzyloxymethylene)dibenzene；diphenylmethanol benzyl ether；diphenylmethyl benzyl ether；benzyloxydiphenylmethane；benzyl benzhydryl ether；Benzene, 1,1'-[(phenylmethoxy)methylene]bis-；benzhydryloxymethylbenzene
• CAS: 26059-49-4
• 化学式: C₂₀H₁₈O
• 分子量: 274.362
• InChiKey: MRDOPPZMPMSASQ-UHFFFAOYSA-N

物化性质

• 熔点：
  50-50.2 °C(Solv: ethanol (64-17-5))
• 沸点：
  382.2±11.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  benzyl diphenylmethyl ether 在 Oxone 、 potassium bromide 作用下， 以 乙腈 为溶剂， 反应 24.5h， 以98%的产率得到二苯甲酮
  参考文献：
  名称：

  Oxidative Debenzylation of N-Benzyl Amides and O-Benzyl Ethers Using Alkali Metal Bromide

  摘要：

  The oxidative debenzylation of N-benzyl amides and O-benzyl ethers was promoted with high efficiency by a bromo radical formed through the oxidation of bromide from alkali metal bromide under mild conditions. This reaction provided the corresponding amides from N-benzyl amides and carbonyl compounds from O-benzyl ethers in high yields.

  DOI：

  10.1021/ol501703y
• 作为产物：
  描述：

  二苯氯甲烷 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 benzyl diphenylmethyl ether
  参考文献：
  名称：

  使用磷酸二苯甲基二苯酯作为烷基化剂的醇和羧酸的O-二苯甲基化

  摘要：

  磷酸二苯甲基二苯酯在温和条件下分别与各种醇和羧酸迅速反应生成二苯甲基醚和酯，而羟酸可在醇位点选择性烷基化。

  DOI：

  10.1016/s0040-4039(01)91201-8

文献信息

• Rapid formation of diphenylmethyl ethers and thioethers using microwave irradiation and protic ionic liquids
  作者：Jarrad M. Altimari、Joshua P. Delaney、Linden Servinis、Jennifer S. Squire、Megan T. Thornton、Simren K. Khosa、Benjamin M. Long、Mark D. Johnstone、Cassandra L. Fleming、Frederick M. Pfeffer、Shane M. Hickey、Matthew P. Wride、Trent D. Ashton、Bronwyn L. Fox、Nolene Byrne、Luke C. Henderson

  DOI：10.1016/j.tetlet.2012.02.011

  日期：2012.4

  Using microwave irradiation and protic ionic liquids (pIL) as co-solvent and catalyst for the synthesis of several diphenylmethyl ethers was achieved. The desired ethers were isolated simply by filtration through a silica plug to remove the pIL and proceeded in high yields (60–98%). These reactions were extremely rapid (10–30 min) and occurred under mild conditions (80 °C). This protocol was also successfully

  使用微波辐射和质子离子液体（pIL）作为助溶剂和催化剂，合成了几种二苯甲基醚。只需通过硅胶塞过滤除去所需的pIL，即可分离出所需的醚，并以高收率（60-98％）进行。这些反应非常迅速（10–30分钟），并且在温和的条件下（80°C）发生。该方案也成功地应用于硫醚的合成。
• B(C₆F₅)₃ catalyzed direct nucleophilic substitution of benzylic alcohols: an effective method of constructing C–O, C–S and C–C bonds from benzylic alcohols
  作者：Shan-Shui Meng、Qian Wang、Gong-Bin Huang、Li-Rong Lin、Jun-Ling Zhao、Albert S. C. Chan

  DOI：10.1039/c8ra05811c

  日期：——

  An efficient and general method of nucleophilic substitution of benzylic alcohols catalyzed by non-metallic Lewis acid B(C6F5)3 was developed. The reaction could be carried out under mild conditions and more than 35 examples of ethers, thioethers and triarylmethanes were constructed in high yields. Some bioactive organic molecules were synthesized directly using the methods.

  开发了一种由非金属路易斯酸B(C 6 F 5 ) 3催化的苯甲醇亲核取代的高效通用方法。该反应可以在温和的条件下进行，并且以高产率构建了超过 35 个醚、硫醚和三芳基甲烷的实例。使用该方法直接合成了一些生物活性有机分子。
• Gold(I)-Catalyzed Synthesis of Unsymmetrical Ethers Using Alcohols as Alkylating Reagents
  作者：Yongxiang Liu、Xiaoyu Wang、Yanshi Wang、Chuan Du、Hui Shi、Shengfei Jin、Chongguo Jiang、Jianyong Xiao、Maosheng Cheng

  DOI：10.1002/adsc.201401097

  日期：2015.3.23

  microwave‐irradiated alcohol‐protecting strategy based on gold catalysis utilizing benzyl alcohol, tert‐butyl alcohol and triphenylmethanol as alkylating reagents has been developed. This protecting strategy has wide functional group tolerance with satisfactory yields for the majority of the selected alcohols. The mechanism of this transformation was probed with oxygen‐18 isotope labelled alcohols assisted by

  基于苄基醇，叔丁醇和三苯甲醇作为烷基化试剂的金催化的微波辐射醇保护策略已经被开发出来。对于大多数选定的醇，该保护策略具有宽泛的官能团耐受性和令人满意的产率。在GC-MS技术和化学动力学实验的辅助下，用氧18同位素标记的醇探索了这种转变的机理。该策略为有机合成中的苄基，叔丁基和三苯甲基醚的制备提供了一种有效，直接和替代的方法。
• Mercury-assisted solvolyses of alkyl halides
  作者：A. McKillop、M.E. Ford

  DOI：10.1016/s0040-4020(01)97118-2

  日期：1974.1

  wide variety of alkyl halides with mercury(I) and/or (II) nitrate in 1,2-dimethoxyethane, mercury(II) acetate in acetic acid, aqueous mercury(II) perchlorate, and mercury(II) perchlorate in alcohol solvents have been investigated; as a result, simple high yield procedures for the conversion of alkyl halides into the corresponding nitrate esters, acetate esters, alcohols and ethers have been developed.

  各种烷基卤与1,2-二甲氧基乙烷中的硝酸汞（I）和/或硝酸盐（II），乙酸中的乙酸汞（II）在乙酸中，高氯酸汞（II）和高氯酸汞（II）的反应在酒精溶剂中已被研究；结果，已经开发了用于将烷基卤化物转化为相应的硝酸酯，乙酸酯，醇和醚的简单的高收率方法。
• Ethers as hydrogen sources in BF₃·OEt₂ promoted reduction of diphenylmethyl alcohols, ethers and esters to hydrocarbons
  作者：Jiaqiang Li、Qing Liu、Hang Shen、Ruofeng Huang、Xiaohui Zhang、Yan Xiong、Changguo Chen

  DOI：10.1039/c5ra14775a

  日期：——

  A novel ether/BF3 reductive system has been described, in which diphenylmethanols and their ether and ester derivatives are used as starting materials. Reductions are performed in ether under reflux and an argon atmosphere, and the addition of extra water is beneficial to this reduction. A series of alkanes are able to be prepared with good to excellent yields. A deuterated experiment exhibits that

  已经描述了一种新颖的醚/ BF 3还原体系，其中二苯甲醇及其醚和酯衍生物被用作起始原料。还原反应是在乙醚中在回流和氩气气氛下进行的，加入额外的水有利于该还原反应。能够以良好或优异的产率制备一系列烷烃。氘代实验表明还原性氢是从醚中产生的。详细讨论了该机制以解释观察到的反应性。