2,5-dihydroxythiophene | 118631-20-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2,5-dihydroxythiophene
• 英文别名: thiophene-2,5-diol；2,5-Dioxythiophen
• CAS: 118631-20-2
• 化学式: C₄H₄O₂S
• 分子量: 116.141
• InChiKey: VORJRCZQADWAQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-dihydroxythiophene 在 水 作用下， 以 乙腈 为溶剂， 生成 5-Hydroxy-3H-thiophen-2-one
  参考文献：
  名称：

  2,5-Dihydroxythiophene

  摘要：

  DOI：

  10.1021/jo00266a044
• 作为产物：
  描述：

  2-噻吩醇 在 hemicucurbit[6]uril 作用下， 以 重水 为溶剂， 生成 2,5-dihydroxythiophene
  参考文献：
  名称：

  Hemicucurbit[6]uril-induced aerobic oxidation of heterocyclic compounds

  摘要：

  The aerobic oxidation of furan in aqueous solution in the presence of HemiQ[16] has been investigated, and the product furan-2,5-diol is stabilized by encapsulation of HemiQ[16], which could be transformed to the dione confirmation in acidic solution and escape from the macrocyclic compound. The H-1 NMR titration experiments of the host-guest interaction at different pH values suggest protonation should improve the encapsulation, and therefore an unique property that HemiQI6] can be protonated has been revealed. The oxidizing kinetics suggests that the procedure is a consecutive reaction with a series of constants k(1) =2.9 x 10(-2) min(-1) , k(2) = 2.7 x 10(-2) min(-1), and k(3) = 5.7 x 10(-3) min(-1), respectively. The kinetic investigation at pD =2.0 indicates the HemiQ[6]-catalytic oxidation of furan could be accelerated by acidification. As a consequence, a plausible mechanism has been established on the above evidences. 2-Methylfuran is employed to give the product 2-methylfuran-5-ol exhibiting a satisfied activity in this aerobic oxidation with the supramolecular catalysis of HemiQ[6], but the oxidation of thiophene is very slow in either neutral or acidic condition. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2013.08.025

文献信息

• HETEROAROMATIC PHTHALONITRILES
  申请人：Laskoski Matthew

  公开号：US20110108755A1

  公开（公告）日：2011-05-12

  Disclosed are an oligomer and a phthalonitrile monomer having the formulas: M is a metal or H. The value n is an integer greater than or equal to 1 for the oligomer and greater than or equal to 0 for the phthalonitrile monomer. Ar 1 and Ar 2 are independently selected aromatic- or heterocyclic-containing groups. Ar 1 , Ar 2 , or both are heteroaromatic or heterocyclic groups containing a nitrogen, sulfur, or oxygen heteroatom. Also disclosed are thermosets and pyrolyzed materials made from the phthalonitrile monomer.

  揭示了具有以下公式的寡聚体和邻苯二腈单体：M是金属或氢。值n是大于或等于1的整数，适用于寡聚体，对于邻苯二腈单体则是大于或等于0的整数。Ar1和Ar2是独立选择的含芳香基或杂环基。Ar1、Ar2或两者都是含有氮、硫或氧杂原子的杂环基或杂环基。还揭示了由邻苯二腈单体制成的热固性材料和热解材料。
• Hemicucurbit[6]uril-induced aerobic oxidation of heterocyclic compounds
  作者：Hang Cong、Takehiko Yamato、Zhu Tao

  DOI：10.1016/j.molcata.2013.08.025

  日期：2013.11

  The aerobic oxidation of furan in aqueous solution in the presence of HemiQ[16] has been investigated, and the product furan-2,5-diol is stabilized by encapsulation of HemiQ[16], which could be transformed to the dione confirmation in acidic solution and escape from the macrocyclic compound. The H-1 NMR titration experiments of the host-guest interaction at different pH values suggest protonation should improve the encapsulation, and therefore an unique property that HemiQI6] can be protonated has been revealed. The oxidizing kinetics suggests that the procedure is a consecutive reaction with a series of constants k(1) =2.9 x 10(-2) min(-1) , k(2) = 2.7 x 10(-2) min(-1), and k(3) = 5.7 x 10(-3) min(-1), respectively. The kinetic investigation at pD =2.0 indicates the HemiQ[6]-catalytic oxidation of furan could be accelerated by acidification. As a consequence, a plausible mechanism has been established on the above evidences. 2-Methylfuran is employed to give the product 2-methylfuran-5-ol exhibiting a satisfied activity in this aerobic oxidation with the supramolecular catalysis of HemiQ[6], but the oxidation of thiophene is very slow in either neutral or acidic condition. (C) 2013 Elsevier B.V. All rights reserved.
• 2,5-Dihydroxythiophene
  作者：Brian Capon、Zhen Ping Wu

  DOI：10.1021/jo00266a044

  日期：1989.3