α-bromo-4,5-dimethoxy-o-xylene | 21852-37-9

• 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: α-bromo-4,5-dimethoxy-o-xylene
• 英文别名: 1-(Bromomethyl)-4,5-dimethoxy-2-methylbenzene
• CAS: 21852-37-9
• 化学式: C₁₀H₁₃BrO₂
• 分子量: 245.116
• InChiKey: OHKLHRKEFHJRDR-UHFFFAOYSA-N

物化性质

• 熔点：
  31.5-33 °C(Solv: hexane (110-54-3))
• 沸点：
  298.1±35.0 °C(Predicted)
• 密度：
  1.337±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  α-bromo-4,5-dimethoxy-o-xylene 在 Orange CRET^.+ 、 锌 作用下， 以 甲醇 为溶剂， 反应 4.08h， 生成 bis-(4,5-dimethoxy-2-methyl-phenyl)-methane
  参考文献：
  名称：

  Radical-Cation Catalysis in the Synthesis of Diphenylmethanes via the Dealkylative Coupling of Benzylic Ethers

  摘要：

  The dealkylative coupling of benzyl alkyl ethers (ArCH(2)OR) to yield the corresponding diarylmethanes (ArCH2Ar) together with dialkoxymethane (ROCH(2)OR) is catalyzed by small amounts of 1-electron oxidants (such as aromatic cation radicals, NO+, etc.) or py an equivalent electrochemical (anodic) method. The catalytic method is successfully employed for the facile synthesis of a novel macrocyclic crown ether 18 that contains a diarylmethane linkage. On the basis of the spectral observation of the radical cation ArCH(2)OR(.+) and the excellent catalytic efficiency with turnover numbers in excess of 10(2), an electron-transfer and an alternative electrophilic chain mechanism are discussed for the dealkylative coupling process.

  DOI：

  10.1021/jo00128a020
• 作为产物：
  描述：

  聚合甲醛 、 3,4-二甲氧基甲苯 在 氢溴酸 、 溶剂黄146 作用下， 以 四氯化碳 为溶剂， 反应 4.0h， 生成 α-bromo-4,5-dimethoxy-o-xylene
  参考文献：
  名称：

  取代的5,6,11,12-四氢加氢二苯并[ a，e ]环辛烯：取代的桑德海默-黄迪因斯的合成，性质和DFT研究

  摘要：

  高应变环乙炔5,6,11,12-四氢二苯并[ a，e在苯环上具有各种取代基的]环辛烯（Sondheimer-Wong diynes）是通过用氯代磷酸二乙酯/六甲基二硅化锂（LiHMDS）然后二异丙基氨基化锂（LDA）一锅法处理相应的甲砜而成功合成的。当将带有不同取代基的两种类型的甲砜混合物进行此操作时，不对称取代的Sondheimer-Wong diynes可以通过逐步分离杂化的乙烯基砜中间体，然后用LDA处理来逐步合成。记录了取代的Sondheimer-Wong diynes的UV-vis吸收光谱和循环伏安图。通过其点击反应以及亲核和亲电加成，研究了取代基对二炔的电子效应。

  DOI：

  10.1021/jo502248p

文献信息

• Molecular Actuator: Redox-Controlled Clam-Like Motion in a Bichromophoric Electron Donor
  作者：Vincent J. Chebny、Ruchi Shukla、Sergey V. Lindeman、Rajendra Rathore

  DOI：10.1021/ol900371m

  日期：2009.5.7

  The one-electron oxidation of tetra methoxydibenzobicyclo[4.4.1]undecane (4) prompts it to undergo a clam-like electromechanical actuation into a cofacially pi-stacked conformer as established by (1) electrochemical analysis, (ii) by the observation of the intense charge-resonance transition in the near IR region in its cation radical spectrum, and (iii) by X-ray crystallographic characterization of the isolated cation radical salt (4(+center dot) SbCl6-).
• Substituted 5,6,11,12-Tetradehydrodibenzo[<i>a</i>,<i>e</i>]cyclooctenes: Syntheses, Properties, and DFT Studies of Substituted Sondheimer–Wong Diynes
  作者：Feng Xu、Lifen Peng、Kenta Shinohara、Takamoto Morita、Suguru Yoshida、Takamitsu Hosoya、Akihiro Orita、Junzo Otera

  DOI：10.1021/jo502248p

  日期：2014.12.5

  Highly strained cyclic acetylenes 5,6,11,12-tetradehydrodibenzo[a,e]cyclooctenes (Sondheimer–Wong diynes) having various substituents on their benzene rings were synthesized successfully by one-pot treatment of the corresponding formyl sulfones with diethyl chlorophosphate/lithium hexamethyldisilazide (LiHMDS) and then lithium diisopropylamide (LDA). When mixtures of two types of formyl sulfones bearing

  高应变环乙炔5,6,11,12-四氢二苯并[ a，e在苯环上具有各种取代基的]环辛烯（Sondheimer-Wong diynes）是通过用氯代磷酸二乙酯/六甲基二硅化锂（LiHMDS）然后二异丙基氨基化锂（LDA）一锅法处理相应的甲砜而成功合成的。当将带有不同取代基的两种类型的甲砜混合物进行此操作时，不对称取代的Sondheimer-Wong diynes可以通过逐步分离杂化的乙烯基砜中间体，然后用LDA处理来逐步合成。记录了取代的Sondheimer-Wong diynes的UV-vis吸收光谱和循环伏安图。通过其点击反应以及亲核和亲电加成，研究了取代基对二炔的电子效应。
• Radical-Cation Catalysis in the Synthesis of Diphenylmethanes via the Dealkylative Coupling of Benzylic Ethers
  作者：Rajendra Rathore、Jay K. Kochi

  DOI：10.1021/jo00128a020

  日期：1995.11

  The dealkylative coupling of benzyl alkyl ethers (ArCH(2)OR) to yield the corresponding diarylmethanes (ArCH2Ar) together with dialkoxymethane (ROCH(2)OR) is catalyzed by small amounts of 1-electron oxidants (such as aromatic cation radicals, NO+, etc.) or py an equivalent electrochemical (anodic) method. The catalytic method is successfully employed for the facile synthesis of a novel macrocyclic crown ether 18 that contains a diarylmethane linkage. On the basis of the spectral observation of the radical cation ArCH(2)OR(.+) and the excellent catalytic efficiency with turnover numbers in excess of 10(2), an electron-transfer and an alternative electrophilic chain mechanism are discussed for the dealkylative coupling process.