2,5-dimethoxy-4-methylphenylmagnesium bromide | 180578-98-7

• 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: 2,5-dimethoxy-4-methylphenylmagnesium bromide
• 英文别名: (2,5-dimethoxy-4-methylphenyl)magnesium bromide
• CAS: 180578-98-7
• 化学式: C₉H₁₁BrMgO₂
• 分子量: 255.394
• InChiKey: SLHJNUVKSIFVJC-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.65
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2,5-dimethoxy-4-methylphenylmagnesium bromide 在 lithium tetrachlorocuprate 、 三溴化硼 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (+/-)-curcuhydroquinone
  参考文献：
  名称：

  Microwave-assisted Efficient Synthesis of Alliodorin and (±)-Curcuhydroquinone

  摘要：

  萜类化合物1和2是利用Li2CuCl4催化下的格氏试剂与烷基/芳基溴化物的偶联反应，以及微波辅助下的烯丙基甲基氧化反应，从易得的原料中合成的，其中，以吸附在SiO2上的SeO2/ButOOH作为关键步骤。

  DOI：

  10.1039/a808057g
• 作为产物：
  描述：

  1-溴-2,5-二甲氧基-4-甲基苯 在 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 生成 2,5-dimethoxy-4-methylphenylmagnesium bromide
  参考文献：
  名称：

  Synthesis, X-ray Structure Analysis and Topochemical Photopolymerization of Substituted 1,6-Bis(2,5-dimethoxyphenyl)hexa-2,4-diynes

  摘要：

  The 1,6-bis(2,5-dimethoxyphenyl)hexa-2,4-diynes 4a-c were obtained from the corresponding 2,5-dimethoxybenzenes 1 by bromination followed by a copper-catalyzed Grignard reaction with 3-bromoprop-1-yne. Catalyzed coupling of the resulting 3-(2,5-dimethoxyphenyl)prop-1-ynes 3 under Hay conditions gave the hexa-2,4-diynes 4a-c in good yields. The molecular structures of the diynes 4a and 4b were determined by X-ray diffraction analysis. In each crystal structure, an unusual 1,6-synperiplanar conformation of the hexa-2,4-diyne unit is observed, with the 1,6-diphenyl substituents arranged in a coplanar orientation. According to the crystal structure data obtained, irradiation of diynes 4a and 4b afforded the deeply-colored, highly-ordered polymers 5a and 5b under topochemical control. Oxidation of 4a and 4b with cerium(IV) ammonium nitrate gave the corresponding 1,6-bis(2,5-dimethoxyphenyl)hexa-2,4-diyne-1,6-diones 6a and 6b.

  DOI：

  10.1002/(sici)1099-0690(199904)1999:4<917::aid-ejoc917>3.0.co;2-b

文献信息

• Multiple-Electron Transfer in a Single Step. Design and Synthesis of Highly Charged Cation-Radical Salts
  作者：Rajendra Rathore、Carrie L. Burns、Mihaela I. Deselnicu

  DOI：10.1021/ol0163474

  日期：2001.9.1

  reversible oxidation at a constant potential of 1.15 V vs SCE to yield robust, multiply charged cation radicals that are isolated in pure form using SbCl(5) as an oxidant. These nanometer-size cation-radical salts are shown to act as efficient "electron sponges" toward a variety of electron donors.

  [结构：见文字]。带有多个氧化还原活性位点的大分子1c和2c是通过2,5-二甲氧基甲苯磺酸溴化物与易于获得的六（4-溴苯基）苯和四（4-溴苯基）甲烷的钯催化有效偶联而合成的。这些大分子电子给体在1.15 V vs SCE的恒定电势下经历可逆氧化，以产生坚固的，带多个电荷的阳离子自由基，这些自由基以SbCl（5）作为氧化剂以纯净形式分离。这些纳米级阳离子自由基盐显示出对各种电子给体有效的“电子海绵”。
• Stereoselective Synthesis of (–)-Heliannuol E by α-Selective ­Propargyl Substitution
  作者：Narihito Ogawa、Chihiro Uematsu、Yuichi Kobayashi

  DOI：10.1055/s-0040-1719844

  日期：2021.12

  This paper describes a stereoselective synthesis of (–)-heliannuol E through intramolecular cyclization of a phenol mesylate. The introduction of the aromatic group was achieved by α-selective propargyl substitution of a propargylic phosphate.

  本文描述了通过苯酚甲磺酸酯的分子内环化反应立体选择性合成 (-)-heliannuol E。芳族基团的引入是通过炔丙基磷酸酯的α-选择性炔丙基取代实现的。
• Efficient Hydrogenation of Sterically Hindered Olefins with Borane−Methyl Sulfide Complex
  作者：R. Rathore、U. Weigand、J. K. Kochi

  DOI：10.1021/jo960357e

  日期：1996.1.1

  Sterically hindered olefins are efficiently reduced to the corresponding alkanes by the borane-methyl sulfide (BMS) complex at room temperature (or below) in dichloromethane containing a mild one-electron oxidant (such as an aromatic cation radical) or by the passage of an anodic current. In an alternative procedure, the hydrogenation of the same (electron-rich) olefins with the EMS complex (in the absence of a one-electron oxidant) is also carried out-in the presence of a strong Bronsted acid (such as HBF4). In the oxidative activation, olefin cation radicals are the first observable intermediates, and separate experiments (including transient electrochemistry) confirm the facile reduction of the olefin cation radical by borane to produce the corresponding alkane. The direct protonation of olefins produces carbocationic intermediates which are also efficiently reduced by borane to the corresponding alkanes. The intermediacy of both olefin cation radicals and carbocations in the hydrogenation procedure with borane is discussed.
• Huenig, Siegfried; Sinzger, Klaus; Kemmer, Martina, European Journal of Organic Chemistry, 1998, # 9, p. 1977 - 1988
  作者：Huenig, Siegfried、Sinzger, Klaus、Kemmer, Martina、Langohr, Uwe、Rieder, Herald、et al.

  DOI：——

  日期：——
• Braun, Manfred; Veith, Reiner; Moll, Gerard, Chemische Berichte, 1985, vol. 118, # 3, p. 1058 - 1070
  作者：Braun, Manfred、Veith, Reiner、Moll, Gerard

  DOI：——

  日期：——