2,5-bis(hydroxymethyl)-3,4-dimethoxy-thiophene | 311312-44-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-bis(hydroxymethyl)-3,4-dimethoxy-thiophene
• 英文别名: [5-(Hydroxymethyl)-3,4-dimethoxythiophen-2-yl]methanol
• CAS: 311312-44-4
• 化学式: C₈H₁₂O₄S
• 分子量: 204.247
• InChiKey: WSAYKTAPALSMNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• 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-bis(hydroxymethyl)-3,4-dimethoxy-thiophene 在 三氯乙酸 作用下， 生成 [5-(5-Hydroxymethyl-3,4-dimethoxy-thiophen-2-ylmethyl)-3,4-dimethoxy-thiophen-2-yl]-methanol
  参考文献：
  名称：

  A new reaction of electron-rich thiophenemethanols

  摘要：

  3-甲氧基噻吩-2-甲醇2在酸性条件下与水和甲醛发生缩合反应，生成双(3-甲氧基-2-噻吩基)甲烷3，以及3与噻吩甲基碳阳离子反应的产物；其他富电子噻吩甲醇8和10的反应类似。

  DOI：

  10.1039/b006513g
• 作为产物：
  描述：

  dimethyl 3,4-dimethoxythiophene-2,5-dicarboxylate 在 lithium aluminium tetrahydride 作用下， 生成 2,5-bis(hydroxymethyl)-3,4-dimethoxy-thiophene
  参考文献：
  名称：

  具有 1、2 和 4 个未取代中碳的硫卟啉：合成和功能化

  摘要：

  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)

  DOI：

  10.1002/ejoc.200300333

文献信息

• New precursors and polymerization route for the preparation of high molecular mass poly(3,4-dialkoxy-2,5-thienylenevinylene)s: low band gap conductive polymers
  作者：Haitao Cheng、Ronald L. Elsenbaumer

  DOI：10.1039/c39950001451

  日期：——

  Bis(sulfoxomethylene) derivatives of dialkoxythiophenes afford high molecular mass conjugated polymers via base, acid and thermally induced elimination of sulfoxide groups.

  通过碱、酸和热诱导消除亚砜基团，二烷氧基噻吩的双（亚砜亚甲基）衍生物可产生高分子共轭聚合物。
• Core-modified porphyrins. Part 6: Effects of lipophilicity and core structures on physicochemical and biological properties in vitro
  作者：Ethel J. Ngen、Thalia S. Daniels、Rajesh S. Murthy、Michael R. Detty、Youngjae You

  DOI：10.1016/j.bmc.2007.12.023

  日期：2008.3.15

  Thiaporphyrins 2-8 were prepared as analogues of 5,20-diphenyl-10,15-bis[4-(carboxymethyleneoxy)-phenyl]-21,23-dithiaporphyrin (1) to examine the effect of structural modifications: substituent changes in meso aryl groups of dithiaporphyrins with one water-solubilizing group (2-5), dihydroxylation of a pyrrole double bond and reduction to dihydroxychlorins (6 and 7), and the removal of two meso aryl groups to give unsubstituted meso positions (8). The impact of these structural modifications was measured in both physicochemical (UV spectra, generation of singlet oxygen, lipophilicity, and aggregate formation) and biological properties (dark toxicity and phototoxicity, cellular uptake, and subeellular localization). Mono-functionalized porphyrins had much higher lipophilicity than di-functionalized porphyrin 1 and, consequently, formed more aggregates in aqueous media. The formation of aggregates might lower the efficiency of lipophilic porphyrins as photosensitizers. Interestingly, dihydroxylation of a core pyrrole group in the dithiaporphyrin core did not affect either the absorption spectrum or the efficiency for generating singlet oxygen. The phototoxicity of dihydroxydithiachlorins mainly depended on their intracellular uptake. The potent phototoxicity of 6, IC50 = 0.18 mu M, was attributed to the extraordinarily high uptake. The intracellular uptake of 6 was about 7.6 times higher than 1. In contrast, thiaporphyrin 8 with only two meso aryl groups was less effective as a photosensitizer, perhaps due to poorer uptake and a lower quantum yield for the generation of singlet oxygen. (C) 2007 Elsevier Ltd. All rights reserved.
• 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)
• A new reaction of electron-rich thiophenemethanols
  作者：R. Alan Aitken、Alasdair N. Garnett

  DOI：10.1039/b006513g

  日期：——

  3-Methoxythiophene-2-methanol 2 undergoes condensation with elimination of water and formaldehyde under acidic conditions to give bis(3-methoxy-2-thienyl)methane 3 and a further product resulting from reaction of 3 with the thienylmethyl carbocation; the other electron-rich thiophenemethanols 8 and 10 react similarly.

  3-甲氧基噻吩-2-甲醇2在酸性条件下与水和甲醛发生缩合反应，生成双(3-甲氧基-2-噻吩基)甲烷3，以及3与噻吩甲基碳阳离子反应的产物；其他富电子噻吩甲醇8和10的反应类似。