2,2'-dimethoxy-5,5'-dibromodiphenylmethane | 2212-47-7

• 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: 2,2'-dimethoxy-5,5'-dibromodiphenylmethane
• 英文别名: bis-(5-bromo-2-methoxyphenyl)methane；bis(5-bromo-2-methoxyphenyl)methane；bis-(5-bromo-2-methoxy-phenyl)-methane；Bis-(5-brom-2-methoxy-phenyl)-methan；5.5'-Dibrom-2.2'-dimethoxy-ditan；4-Bromo-2-[(5-bromo-2-methoxyphenyl)methyl]-1-methoxybenzene
• CAS: 2212-47-7
• 化学式: C₁₅H₁₄Br₂O₂
• 分子量: 386.083
• InChiKey: XNWPHBJZXPVUDL-UHFFFAOYSA-N

物化性质

• 熔点：
  107.5 °C
• 沸点：
  424.0±40.0 °C(Predicted)
• 密度：
  1.549±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2'-dimethoxy-5,5'-dibromodiphenylmethane 在 chromium(VI) oxide 、 溶剂黄146 作用下， 生成 5,5'-二溴-2,2'-二甲氧基-二苯甲酮
  参考文献：
  名称：

  Diels; Rosenmund, Chemische Berichte, 1906, vol. 39, p. 2362

  摘要：

  DOI：
• 作为产物：
  描述：

  4-溴苯酚 在 氢氧化钾 、 硫酸 、 丙酮 作用下， 生成 2,2'-dimethoxy-5,5'-dibromodiphenylmethane
  参考文献：
  名称：

  THE STABILITY OF 2,2'-DIHYDROXYDIPHENYLMETHANE

  摘要：

  DOI：

  10.1021/jo01192a003

文献信息

• A simple and inexpensive procedure for chloromethylation of certain aromatic compounds
  作者：Alexander McKillop、Fereidon Abbasi Madjdabadi、David A. Long

  DOI：10.1016/s0040-4039(00)81809-2

  日期：1983.1

  Reaction of a range of aromatic compounds with methoxyacetyl chloride and aluminium chloride in either nitromethane or carbon disulphide results in chloromethylation in good to excellent yield.

  一系列芳族化合物与甲氧基乙酰氯和氯化铝在硝基甲烷或二硫化碳中的反应导致氯甲基化，收率好至极佳。
• Acid-promoted rearrangement of arylmethyl azides: applications toward the synthesis of N-arylmethyl arenes and polycyclic heteroaromatic compounds
  作者：Jumreang Tummatorn、Charnsak Thongsornkleeb、Somsak Ruchirawat

  DOI：10.1016/j.tet.2012.04.014

  日期：2012.6

  nucleophiles. We report here the reaction of this iminium ion with aromatic nucleophiles to give N-arylmethyl arenes and the reaction with heteroaromatic compounds to give fused polycyclic heteroaromatic products in a formal [4+2] cycloaddition. The short synthesis of isocrytolepine, an antimalarial agent, further demonstrated the utility of this process.

  酸促进的Aubé-Schmidt对芳基甲基叠氮化物的重排提供了有用的原位亚胺离子中间体，可以被各种亲核试剂有效地捕获。我们在此报告此亚胺离子与芳族亲核试剂的反应，以生成N-芳基甲基芳烃；与杂芳族化合物的反应，以在正式的[4 + 2]环加成反应中得到稠合的多环杂芳族产物。异辛酚（抗疟药）的短合成进一步证明了该方法的实用性。
• Functional Ionic Liquids as Efficient and Recyclable Catalysts for the Methylation of Formaldehyde with Aromatics
  作者：Heyuan Song、Fuxiang Jin、Ronghua Jin、Meirong Kang、Zhen Li、Jing Chen

  DOI：10.1007/s10562-016-1750-5

  日期：2016.7

  Methylation of formaldehyde with various aromatics under functional ionic liquids catalysis has been developed. Among the ionic liquids investigated, triphenyl-(4-sulfobutyl)-phosphonium triflate ([TTPBs][CF3SO3]) showed high activity and afforded excellent yields of diarylmethane derivatives. A mechanism for the catalytic performance of [TTPBs][CF3SO3] is proposed. Besides, the catalyst can simply

  已经开发了在功能性离子液体催化下甲醛与各种芳烃的甲基化。在所研究的离子液体中，三苯基-(4-磺丁基)-鏻三氟甲磺酸盐 ([TTPBs][CF3SO3]) 显示出高活性并提供了优异的二芳基甲烷衍生物收率。提出了[TTPBs][CF3SO3]催化性能的机制。此外，该催化剂可以通过离心简单地从反应混合物中分离出来，并且可以循环使用十次，而没有明显的活性损失。 图文摘要 使用高效且可回收的功能性离子液体作为催化剂，通过甲醛与芳烃的甲基化成功合成了二芳基甲烷衍生物，收率极好和选择性是在无溶剂条件下获得的。该催化剂至少连续重复使用十次，其催化活性没有明显损失。同时，探索了催化剂的可用性。
• A Fenton Approach to Aromatic Radical Cations and Diarylmethane Synthesis
  作者：Robert Crowley III、Berkley Lujan、Alex Martinez、Roni Manasi、Justin D. DeBow、Kevin G. M. Kou

  DOI：10.1021/acs.joc.3c01505

  日期：2023.11.3

  carbon-centered radicals to add to electron-deficient systems is a well-precedented process. By coupling the Fe(II)-mediated Fenton reaction with the Fe(III)-mediated single-electron oxidation of anisolic compounds, we demonstrate how electron-rich carbon-centered radicals can react with electron-rich arenes through a radical-polar cascade pathway. This bioinspired approach produces diarylmethane derivatives from

  操纵以碳为中心的自由基以添加到缺电子系统中是一个有先例的过程。通过将 Fe(II) 介导的芬顿反应与 Fe(III) 介导的茴香醇化合物的单电子氧化耦合，我们证明了富电子碳中心自由基如何通过自由基-极性级联与富电子芳烃反应途径。这种仿生方法从简单的未官能化前体生产二芳基甲烷衍生物。
• Evidence for Mono- and Bisdentate Boronate Complexes of Glucose in the Furanose Form. Application of 1JC-C Coupling Constants as a Structural Probe
  作者：Jens C. Norrild、Hanne Eggert

  DOI：10.1021/ja00110a003

  日期：1995.2

  Complex formation between aromatic boronic acids and D-glucose was investigated by H-1 and C-13 NMR spectroscopy both under neutral nonaqueous and alkaline aqueous conditions. The structure of the bisdentate complex between 2,2'-dimethoxydiphenylmethane-5,5'-diboronic acid and glucose was reinvestigated and reassigned. The reactions studied are shown in Scheme 1. The complexes contain in all cases the furanose form of glucose bound to two boronic acid groups where the one is bound in the (1,2) position. The binding site for the second boronic acid group is (3,5) under neutral nonaqueous conditions. In aqueous alkaline solution the second binding site varies from the mono- to the diboronic acid. The second monoboronic acid binds to the (3,5,6) position in a tris coordinating manner, and the diboronic acid binds its second boronic acid group only to the (5,6) position. Two closely related complexes (ratio 4:1) are observed in the spectra with the monoboronic acid. This is ascribed to diastereomerism from the 1,2-complexed stereocenter. (1)J(C-C) are used in the structure assignment. Exceptionally low values of 34-35 Hz for (1)J(C-C) are measured for vicinal diols when the O-C-C-O fragment becomes incorporated in a five membered ring as is the case in cyclic boronic esters with a vicinal ester bonding.