2,5-di(hydroxymethyl)-3,4-ethylenedioxythiophene | 350474-52-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-di(hydroxymethyl)-3,4-ethylenedioxythiophene
• 英文别名: [5-(Hydroxymethyl)-2,3-dihydrothieno[3,4-b][1,4]dioxin-7-yl]methanol
• CAS: 350474-52-1
• 化学式: C₈H₁₀O₄S
• 分子量: 202.231
• InChiKey: GCXKFRTWPAMHET-UHFFFAOYSA-N

物化性质

• 沸点：
  410.3±45.0 °C(Predicted)
• 密度：
  1.492±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  87.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,5-di(hydroxymethyl)-3,4-ethylenedioxythiophene 在 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 反应 96.0h， 以66%的产率得到2,3-二氢苯并[3,4-B][1,4]二恶英-5,7-二苯甲醛
  参考文献：
  名称：

  Effect of 3,4-ethylenedioxy-extension of thiophene core on the DNA/RNA binding properties and biological activity of bisbenzimidazole amidines

  摘要：

  Novel bisbenzimidazoles (4-6), characterized by 3,4-ethylenedioxy-extension of thiophene core, revealed pronounced affinity and strong thermal stabilization effect toward ds-DNA. They interact within ds-DNA grooves as dimmers or even oligomers and agglomerate along ds-RNA. Compounds 4-6 have shown moderate to strong antiproliferative effect toward panel of eight carcinoma cell lines. Compound 5 displayed the best inhibitory potential and in equitoxic concentration (IC50 = 1 x 10 (6) M) induced accumulation of cells in G2/M phase after 48 h of incubation. Fluorescence microscopy showed that 5 entered into live HeLa cells within 30 min, but did not accumulate in nuclei even after 2.5 h. Compound 5 inhibited the growth of Trypanosome cruzi epimastigotes (IC50 = 4.3 x 10 (6) M). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.071
• 作为产物：
  描述：

  2,3-二氢-噻吩并[3,4-b]-1,4-二噁英-5,7-二羧酸二乙酯 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以87.9%的产率得到2,5-di(hydroxymethyl)-3,4-ethylenedioxythiophene
  参考文献：
  名称：

  Effect of 3,4-ethylenedioxy-extension of thiophene core on the DNA/RNA binding properties and biological activity of bisbenzimidazole amidines

  摘要：

  Novel bisbenzimidazoles (4-6), characterized by 3,4-ethylenedioxy-extension of thiophene core, revealed pronounced affinity and strong thermal stabilization effect toward ds-DNA. They interact within ds-DNA grooves as dimmers or even oligomers and agglomerate along ds-RNA. Compounds 4-6 have shown moderate to strong antiproliferative effect toward panel of eight carcinoma cell lines. Compound 5 displayed the best inhibitory potential and in equitoxic concentration (IC50 = 1 x 10 (6) M) induced accumulation of cells in G2/M phase after 48 h of incubation. Fluorescence microscopy showed that 5 entered into live HeLa cells within 30 min, but did not accumulate in nuclei even after 2.5 h. Compound 5 inhibited the growth of Trypanosome cruzi epimastigotes (IC50 = 4.3 x 10 (6) M). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.071

文献信息

• Thiaporphyrins with One, Two and Four Unsubstitutedmeso-Carbons: Synthesis and Functionalization
  作者：Neeraj Agarwal、C.-H. Hung、M. Ravikanth

  DOI：10.1002/ejoc.200300333

  日期：2003.10

  Thiaporphyrins with one, two and four unsubstituted meso carbons were synthesized from easily available thiophene diols. The reactivity at these carbons was demonstrated by carrying out series of reactions and some very useful functional groups were introduced. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  从容易获得的噻吩二醇合成具有 1、2 和 4 个未取代的内碳原子的硫卟啉。通过进行一系列反应并引入了一些非常有用的官能团，证明了这些碳的反应性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)