5-ethylthiophen-2-yl (3-methoxycarbonyl)propyl ketone | 27383-00-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-ethylthiophen-2-yl (3-methoxycarbonyl)propyl ketone
• 英文别名: Methyl 5-(5-ethylthiophen-2-yl)-5-oxopentanoate
• CAS: 27383-00-2
• 化学式: C₁₂H₁₆O₃S
• 分子量: 240.323
• InChiKey: XBBGOVYKQCITMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-ethylthiophen-2-yl (3-methoxycarbonyl)propyl ketone 、 对甲苯磺酰肼 以 甲醇 为溶剂， 反应 24.0h， 以74%的产率得到methyl 5-(5-ethylthiophen-2-yl)-5-(2-tosylhydrazono)-valerate
  参考文献：
  名称：

  Synthesis and properties of novel methanofullerenes having ethylthienyl and/or n-pentyl group for photovoltaic cells

  摘要：

  Novel methanofullerenes 3 having ethylthienyl and/or n-pentyl groups were designed and synthesized for the purpose of developing new acceptors for an organic photovoltaic cell with higher performance than that of the [6,6]-phenyl-C(61)-butylic acid methyl ester (PCBM) used as the standard acceptor. The electronic absorption spectra and cyclic voltammetry (CV) of 3, PCBM, and [6,6]-(thiophene-2-yl)-C(61)-butylic acid methyl ester (ThCBM) were measured to estimate solubility and reduction potentials as characteristics of n-type semiconductor for organic photovoltaic devices. The CV measurements revealed reversible reduction waves for all of the methanofullerenes and the first reduction potentials of the n-pentyl-substituted 1-(5-ethylthiophene-2-yl)-[6,6]-methanofullerene[60] (3b) and 1-phenyl-[6,6]-methanofullerene-[60] (3c) were negatively shifted compared to those of the corresponding terminal methyl ester-substituted homologues (3a and PCBM). The performances of photovoltaic devices consisting of 3b and 3c were slightly higher than those of PCBM. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.089
• 作为产物：
  描述：

  2-乙基噻吩 、 4-氯甲酰基丁酸甲酯 在 aluminum (III) chloride 作用下， 以 乙腈 为溶剂， 以49%的产率得到5-ethylthiophen-2-yl (3-methoxycarbonyl)propyl ketone
  参考文献：
  名称：

  Synthesis and properties of novel methanofullerenes having ethylthienyl and/or n-pentyl group for photovoltaic cells

  摘要：

  Novel methanofullerenes 3 having ethylthienyl and/or n-pentyl groups were designed and synthesized for the purpose of developing new acceptors for an organic photovoltaic cell with higher performance than that of the [6,6]-phenyl-C(61)-butylic acid methyl ester (PCBM) used as the standard acceptor. The electronic absorption spectra and cyclic voltammetry (CV) of 3, PCBM, and [6,6]-(thiophene-2-yl)-C(61)-butylic acid methyl ester (ThCBM) were measured to estimate solubility and reduction potentials as characteristics of n-type semiconductor for organic photovoltaic devices. The CV measurements revealed reversible reduction waves for all of the methanofullerenes and the first reduction potentials of the n-pentyl-substituted 1-(5-ethylthiophene-2-yl)-[6,6]-methanofullerene[60] (3b) and 1-phenyl-[6,6]-methanofullerene-[60] (3c) were negatively shifted compared to those of the corresponding terminal methyl ester-substituted homologues (3a and PCBM). The performances of photovoltaic devices consisting of 3b and 3c were slightly higher than those of PCBM. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.089