5-(dimethoxymethyl)-2-nitrothiophene | 17375-68-7

• 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: 5-(dimethoxymethyl)-2-nitrothiophene
• 英文别名: 2-dimethoxymethyl-5-nitrothiophene；2-(Dimethoxymethyl)-5-nitrothiophene；2-(dimethoxymethyl)-5-nitrothiophene
• CAS: 17375-68-7
• 化学式: C₇H₉NO₄S
• 分子量: 203.219
• InChiKey: PRCXPLVGLWVGFT-UHFFFAOYSA-N

物化性质

• 沸点：
  255.5±40.0 °C(Predicted)
• 密度：
  1.323±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  92.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(dimethoxymethyl)-2-nitrothiophene 、 烯丙基溴化镁 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 生成 5-(Dimethoxymethyl)-2-nitro-3-prop-2-enylthiophene
  参考文献：
  名称：

  Synthesis of a series of nitrothiophenes with basic or electrophilic substituents and evaluation as radiosensitizers and as bioreductively activated cytotoxins

  摘要：

  A series of 2- and 3-nitrothiophene-5-carboxamides bearing N-(omega-aminoalkyl) side chains has been prepared by treatment of the thiophenecarbonyl chloride with the appropriate (protected) omega-aminoalkylamine. Analogous N-(oxiranylmethyl)nitrothiophene-5-carboxamides have been synthesized by epoxidation of the corresponding N-allylamide. Compounds in both classes were evaluated in vitro both as radiosensitizers of hypoxic mammalian cells and as selective bioreductively activated cytotoxins. The most potent radiosensitizers were those agents with strong tertiary amine bases or oxiranes in the side chain. Studies in vivo showed that 2-methyl-N-[2-(dimethylamino)ethyl]-3-nitrothiophene-5-carboxamide caused slight radiosensitization of the KHT sarcoma in mice given 0.34 mmol kg-1. However, administration of this and related tertiary amines at higher doses was precluded by systemic toxicity.

  DOI：

  10.1021/jm00111a029
• 作为产物：
  描述：

  甲醇 、 5-硝基噻吩-2-甲醛 在 盐酸 作用下， 反应 0.75h， 以100%的产率得到5-(dimethoxymethyl)-2-nitrothiophene
  参考文献：
  名称：

  Synthesis of a series of nitrothiophenes with basic or electrophilic substituents and evaluation as radiosensitizers and as bioreductively activated cytotoxins

  摘要：

  A series of 2- and 3-nitrothiophene-5-carboxamides bearing N-(omega-aminoalkyl) side chains has been prepared by treatment of the thiophenecarbonyl chloride with the appropriate (protected) omega-aminoalkylamine. Analogous N-(oxiranylmethyl)nitrothiophene-5-carboxamides have been synthesized by epoxidation of the corresponding N-allylamide. Compounds in both classes were evaluated in vitro both as radiosensitizers of hypoxic mammalian cells and as selective bioreductively activated cytotoxins. The most potent radiosensitizers were those agents with strong tertiary amine bases or oxiranes in the side chain. Studies in vivo showed that 2-methyl-N-[2-(dimethylamino)ethyl]-3-nitrothiophene-5-carboxamide caused slight radiosensitization of the KHT sarcoma in mice given 0.34 mmol kg-1. However, administration of this and related tertiary amines at higher doses was precluded by systemic toxicity.

  DOI：

  10.1021/jm00111a029

文献信息

• The use of electroosmotic flow as a pumping mechanism for semi-preparative scale continuous flow synthesis
  作者：Charlotte Wiles、Paul Watts、Stephen J. Haswell

  DOI：10.1039/b614559k

  日期：——

  By employing a series of reactions we demonstrate the use of electroosmotic flow as a continuous pumping mechanism suitable for semi-preparative scale synthesis, affording an array of small organic compounds, of analytical purity, with yields ranging from 0.57–1.71 g h−1.

  通过采用一系列反应，我们证明了将电渗流作为一种连续泵送机制应用于半制备规模的合成，能够获得一系列小有机化合物，其分析纯度下的产率范围为每小时0.57至1.71克。
• Acid-catalysed synthesis and deprotection of dimethyl acetals in a miniaturised electroosmotic flow reactor
  作者：Charlotte Wiles、Paul Watts、Stephen J. Haswell

  DOI：10.1016/j.tet.2005.03.082

  日期：2005.5

  Through incorporating a series of polymer-supported acid catalysts into a miniaturised EOF-based flow reactor, we demonstrate a clean and efficient technique for the protection of aldehydes as their respective dimethyl acetal. In addition, we also report the acid catalysed deacetalisation of 11 dimethyl acetals to their respective aldehyde. In all cases, the compounds described are obtained in high yield (> 95%) and excellent purity (> 99%) without the need for further product purification. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis of a series of nitrothiophenes with basic or electrophilic substituents and evaluation as radiosensitizers and as bioreductively activated cytotoxins
  作者：Michael D. Threadgill、Paul Webb、Peter O'Neill、Matthew A. Naylor、Miriam A. Stephens、Ian J. Stratford、Shirley Cole、Gerald E. Adams、E. Martin Fielden

  DOI：10.1021/jm00111a029

  日期：1991.7

  A series of 2- and 3-nitrothiophene-5-carboxamides bearing N-(omega-aminoalkyl) side chains has been prepared by treatment of the thiophenecarbonyl chloride with the appropriate (protected) omega-aminoalkylamine. Analogous N-(oxiranylmethyl)nitrothiophene-5-carboxamides have been synthesized by epoxidation of the corresponding N-allylamide. Compounds in both classes were evaluated in vitro both as radiosensitizers of hypoxic mammalian cells and as selective bioreductively activated cytotoxins. The most potent radiosensitizers were those agents with strong tertiary amine bases or oxiranes in the side chain. Studies in vivo showed that 2-methyl-N-[2-(dimethylamino)ethyl]-3-nitrothiophene-5-carboxamide caused slight radiosensitization of the KHT sarcoma in mice given 0.34 mmol kg-1. However, administration of this and related tertiary amines at higher doses was precluded by systemic toxicity.