2,3-diethynyl 5,6-dimethylhydroquinone | 198124-89-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,3-diethynyl 5,6-dimethylhydroquinone
• 英文别名: 2,3-Diethynyl-5,6-dimethylbenzene-1,4-diol
• CAS: 198124-89-9
• 化学式: C₁₂H₁₀O₂
• 分子量: 186.21
• InChiKey: FKXUTIISOCJBJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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-diethynyl 5,6-dimethylhydroquinone 在 氘代甲醇 作用下， 反应 8.0h， 生成 1,2-Bis(2-deuterioethynyl)-3,6-dideuteriooxy-4,5-dimethylbenzene
  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-Dimethyl-5,6-bis(2-trimethylsilylethynyl)benzene-1,4-diol 在 potassium fluoride 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以52%的产率得到2,3-diethynyl 5,6-dimethylhydroquinone
  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。
• Method of synthesizing isoindolequinones and derivatives thereof
  申请人：The University of Akron

  公开号：US05889185A1

  公开（公告）日：1999-03-30

  A method of synthesizing isoindolequinones comprising the step of reacting a 2,3-di(ethynyl)hydroquinone with a hydride selected from the group consisting of Group 15 and Group 16 hydrides, wherein said step of reacting takes place in an oxygen free environment.

  一种合成异吲哚醌的方法，包括以下步骤：将2,3-二（乙炔基）氢醌与选择自第15组和第16组的氢化物反应，其中所述反应步骤在无氧环境中进行。
• US5889185A
  申请人：——

  公开号：US5889185A

  公开（公告）日：1999-03-30
• [EN] METHOD OF SYNTHESIZING ISOINDOLEQUINONES AND DERIVATIVES THEREOF<br/>[FR] PROCEDE DE SYNTHESE D'ISO-INDOLEQUINONES ET DERIVES CORRESPONDANTS
  申请人：THE UNIVERSITY OF AKRON

  公开号：WO1998046567A1

  公开（公告）日：1998-10-22

  (EN) A method of synthesizing isoindolequinones comprising the step of reacting a 2,3-di(ethynyl)hydroquinone with a hydride selected from the group consisting of Group 15 and Group 16 hydrides, wherein said step of reacting takes place in an oxygen free environment.(FR) Cette invention se rapporte à un procédé de synthèse d'iso-indolequinones consistant à faire réagir une 2,3-di(éthynyl)hydroquinone avec un hydrure sélectionné dans le groupe constitué par des hydrures du groupe 15 et du groupe 16, dans un environnement ne contenant pas d'oxygène.