2,3-Dimethyl-5,6-bis(2-trimethylsilylethynyl)benzene-1,4-diol | 198124-88-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,3-Dimethyl-5,6-bis(2-trimethylsilylethynyl)benzene-1,4-diol
• CAS: 198124-88-8
• 化学式: C₁₈H₂₆O₂Si₂
• 分子量: 330.574
• InChiKey: RQYMAXRBCUEYFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-Dimethyl-5,6-bis(2-trimethylsilylethynyl)benzene-1,4-diol 在 potassium fluoride 、 二(氰基苯)二氯化钯 、 三苯基膦 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 生成 2-Isopropyl-1,3,5,6-tetramethylisoindole-4,7-quinone
  参考文献：
  名称：

  A Novel High-Yield Synthesis of Substituted Isoindolequinones

  摘要：

  The high-yield, general, one-pot synthesis of substituted isoindolequinones, a group of important radiosensitizers which sensitize hypoxic cells to the lethal effect of radiation in cancer radiotherapy, is described. Primary amines react with 2,3-bis[2-(trimethylsilyl)ethynyl]-5,6-dimethylhydroquinone (2) in methanol at room temperature under an inert atmosphere to give substituted isoindole-quinones 2-alkyl-1,3,5,6-tetramethylisoindole-4,7-quinone (4) in almost quantitative yields. Moderate yields of 4 are also obtained using 2,3-diethynyl-5,6-dimethylhydroquinone (3) and amines as reactant and solvent under the similar conditions. Tris(2-aminoethyl)amine (TREN) reacts with 2 in MeOH/THF on reflux to produce the isoindolequinone derivative of TREN. Water with 2 on reflux in MeOH forms an isobenzofuranquinone. This indicates that the formation of similar heterocycles from small molecules (e.g., Group VA and VIA hydrides) and 2 is likely. Readily synthesizable starting materials, ease of chromatographic isolation of the product, reaction generality, use of no catalyst, and cost-effective environmentally benign solvents such as MeOH/EtOH make this novel reaction simple and convenient.

  DOI：

  10.1021/jo971671r
• 作为产物：
  描述：

  2,3-diiodo-5,6-dimethylhydroquinone 、 三甲基乙炔基硅 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二异丙胺 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以50.2%的产率得到2,3-Dimethyl-5,6-bis(2-trimethylsilylethynyl)benzene-1,4-diol
  参考文献：
  名称：

  A Novel High-Yield Synthesis of Substituted Isoindolequinones

  摘要：

  The high-yield, general, one-pot synthesis of substituted isoindolequinones, a group of important radiosensitizers which sensitize hypoxic cells to the lethal effect of radiation in cancer radiotherapy, is described. Primary amines react with 2,3-bis[2-(trimethylsilyl)ethynyl]-5,6-dimethylhydroquinone (2) in methanol at room temperature under an inert atmosphere to give substituted isoindole-quinones 2-alkyl-1,3,5,6-tetramethylisoindole-4,7-quinone (4) in almost quantitative yields. Moderate yields of 4 are also obtained using 2,3-diethynyl-5,6-dimethylhydroquinone (3) and amines as reactant and solvent under the similar conditions. Tris(2-aminoethyl)amine (TREN) reacts with 2 in MeOH/THF on reflux to produce the isoindolequinone derivative of TREN. Water with 2 on reflux in MeOH forms an isobenzofuranquinone. This indicates that the formation of similar heterocycles from small molecules (e.g., Group VA and VIA hydrides) and 2 is likely. Readily synthesizable starting materials, ease of chromatographic isolation of the product, reaction generality, use of no catalyst, and cost-effective environmentally benign solvents such as MeOH/EtOH make this novel reaction simple and convenient.

  DOI：

  10.1021/jo971671r

文献信息

• A novel tandem bicyclization to form an indenopyran ring system
  作者：Manisha Chakraborty、David B. McConville、Takeshi Saito、Huihan Meng、Peter L. Rinaldi、Claire A. Tessier、Wiley J. Youngs

  DOI：10.1016/s0040-4039(98)01779-1

  日期：1998.11

  A new palladium-copper catalyzed intramolecular acetylene-zipper type bicyclization between alkyne and hydroxy functionality of an alkynyl hydroquinone has been observed to give a highly conjugated ring system.

  已经观察到在炔烃和炔基对苯二酚的羟基官能团之间的新的钯-铜催化的分子内乙炔-拉链型双环化产生了高度共轭的环体系。