2,3-bis(bromomethyl)-1,4-dimethoxy-5,6-dimethylbenzene | 205862-10-8

• 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: 2,3-bis(bromomethyl)-1,4-dimethoxy-5,6-dimethylbenzene
• 英文别名: 1,2-Bis(bromomethyl)-3,6-dimethoxy-4,5-dimethylbenzene
• CAS: 205862-10-8
• 化学式: C₁₂H₁₆Br₂O₂
• 分子量: 352.066
• InChiKey: CLMJIXGLLGQYLV-UHFFFAOYSA-N

物化性质

• 沸点：
  371.1±37.0 °C(Predicted)
• 密度：
  1.537±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  2,3-bis(bromomethyl)-1,4-dimethoxy-5,6-dimethylbenzene 在 盐酸 、 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 作用下， 以 四氢呋喃 、 四氯化碳 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.33h， 生成
  参考文献：
  名称：

  Diels−Alder Reactions through Reversible Encapsulation

  摘要：

  Experimental details are given for the preparation of large self-complementary molecules capable of assembly into pseudospherical capsules. These structures exist as hydrogen bended diners in organic solvents, and they form and dissipate on a time scale that permits direct NMR observation of the reversible encapsulation of smaller molecules. The cavity is roomy enough to accommodate more than one molecule, and two solvent molecules such as benzene appear to occupy the resting state of the capsules. Liberation of these solvent molecules is responsible for the unexpected thermodynamic parameters of the encapsulation process. A bimolecular reaction-the Diels-Alder reaction-is shown to be accelerated by the capsule as both reactants can occupy the capsule concurrently. Size selectivity, saturation kinetics, and product inhibition studies point to a reaction that takes place within the capsule.

  DOI：

  10.1021/ja973898+
• 作为产物：
  描述：

  溴甲基甲基醚 、 1,4-二甲氧基-2,3-甲基苯 在 硫酸 作用下， 反应 24.0h， 以91%的产率得到2,3-bis(bromomethyl)-1,4-dimethoxy-5,6-dimethylbenzene
  参考文献：
  名称：

  Diels−Alder Reactions through Reversible Encapsulation

  摘要：

  Experimental details are given for the preparation of large self-complementary molecules capable of assembly into pseudospherical capsules. These structures exist as hydrogen bended diners in organic solvents, and they form and dissipate on a time scale that permits direct NMR observation of the reversible encapsulation of smaller molecules. The cavity is roomy enough to accommodate more than one molecule, and two solvent molecules such as benzene appear to occupy the resting state of the capsules. Liberation of these solvent molecules is responsible for the unexpected thermodynamic parameters of the encapsulation process. A bimolecular reaction-the Diels-Alder reaction-is shown to be accelerated by the capsule as both reactants can occupy the capsule concurrently. Size selectivity, saturation kinetics, and product inhibition studies point to a reaction that takes place within the capsule.

  DOI：

  10.1021/ja973898+

文献信息

• Reaction of Trialkyl(dibromomethyl)silanes or 1,2-Bis(dibromomethyl)benzene with Triorganomanganates. A Facile and Selective Synthesis of Alkenylsilanes and 1,2-Diaryl-1,2-dihydrobenzocyclobutenes
  作者：Hirotada Kakiya、Hiroshi Shinokubo、Koichiro Oshima

  DOI：10.1246/bcsj.73.2139

  日期：2000.9

  stereoselectivity in good yields. The reaction of trialkyl(dibromomethyl)silanes with alkylmagnesium halides proceeded in the presence of a catalytic amount of manganese(II) chloride. Treatment of 1,2-bis(dibromomethyl)benzene with triphenylmanganate gave 1,2-diphenyl-1,2-dihydrobenzocyclobutene.

  用衍生自氯化锰 (II) 和三摩尔量的格氏试剂或烷基锂的三烷基锰酸盐处理三烷基（二溴甲基）硅烷，以良好的收率提供具有高立体选择性的（E）-1-三烷基甲硅烷基-1-烯烃。三烷基（二溴甲基）硅烷与烷基卤化镁的反应在催化量的氯化锰（II）存在下进行。用三苯基锰酸盐处理 1,2-双(二溴甲基)苯得到 1,2-二苯基-1,2-二氢苯并环丁烯。