2,3-diiodo-5,6-dimethylhydroquinone | 144182-03-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,3-diiodo-5,6-dimethylhydroquinone
• 英文别名: 2,3-Diiodo 5,6-dimethylhydroquinone；2,3-diiodo-5,6-dimethylbenzene-1,4-diol
• CAS: 144182-03-6
• 化学式: C₈H₈I₂O₂
• 分子量: 389.959
• InChiKey: ZBPNKLBRRZNBRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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-diiodo-5,6-dimethylhydroquinone 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 作用下， 以 甲苯 为溶剂， 反应 10.0h， 生成 2-(2-Hydroxy-3,4-dimethyl-1-trimethylsilanylethynyl-indeno[1,2-c]chromen-6-yl)-5,6-dimethyl-3-trimethylsilanylethynyl-benzene-1,4-diol
  参考文献：
  名称：

  新型串联双环化形成茚并吡喃环系统

  摘要：

  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。

  DOI：

  10.1016/s0040-4039(98)01779-1

文献信息

• Redox-controlled Bergman cycloaromatizations. Designed enediynes with DNA-cleaving properties and antitumor activity
  作者：K. C. Nicolaou、A. Liu、Z. Zeng、S. McComb

  DOI：10.1021/ja00050a006

  日期：1992.11

  Enediynes 7 and 9 were designed for their potential to act as radical-generating species upon oxidation to the corresponding quinone. Their synthesis entailed a chromium-nickel-mediated ring closure of iodo aldehyde 6. Investigations with these molecules and their derivatives 8 and 10 demonstrated the anticipated acceleration of the Bergman cycloaromatization of the oxidized species as compared to

  烯二炔 7 和 9 被设计为具有在氧化成相应醌时作为自由基生成物质的潜力。它们的合成需要铬-镍介导的碘醛 6 闭环。 对这些分子及其衍生物 8 和 10 的研究表明，与还原化合物相比，氧化物质的 Bergman 环芳构化和有效的 DNA 裂解和抗肿瘤特性
• 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，包括将2,3-二(乙炔基)氢醌与来自第15和第16族氢化物的氢化物反应，其中所述反应步骤在无氧环境下进行。
• Reactions of Primary and Secondary Amines with Substituted Hydroquinones:  Nuclear Amination, Side-Chain Amination, and Indolequinone Formation
  作者：Manisha Chakraborty、David B. McConville、Yanhui Niu、Claire A. Tessier、Wiley J. Youngs

  DOI：10.1021/jo980541v

  日期：1998.10.1
• A Novel High-Yield Synthesis of Substituted Isoindolequinones
  作者：Manisha Chakraborty、David B. McConville、Gerald F. Koser、Claire A. Tessier、Takeshi Saito、Peter L. Rinaldi、Wiley J. Youngs

  DOI：10.1021/jo971671r

  日期：1997.11.1

  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.
• US5889185A
  申请人：——

  公开号：US5889185A

  公开（公告）日：1999-03-30