2-[α-(p-tolyl)-α-hydroxymethyl]-3,4-(dimethoxy)-thiophene | 1229863-57-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[α-(p-tolyl)-α-hydroxymethyl]-3,4-(dimethoxy)-thiophene
• 英文别名: (3,4-Dimethoxythiophen-2-yl)-(4-methylphenyl)methanol
• CAS: 1229863-57-3
• 化学式: C₁₄H₁₆O₃S
• 分子量: 264.345
• InChiKey: KNLXJGVXZXDCCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  吡咯 、 2-[α-(p-tolyl)-α-hydroxymethyl]-3,4-(dimethoxy)-thiophene 、 间硝基苯甲醛 在 丙酸 作用下， 反应 3.0h， 生成 β-2,3-dimethoxy-meso-10-(p-tolyl)-5,15-bis(m-nitrophenyl)-22-thiacorrole
  参考文献：
  名称：

  Synthesis and Studies of Thiacorroles

  摘要：

  The first examples of stable 22-thiacorroles containing a direct pyrrole pyrrole bond were synthesized using thiophene monocarbinols as key precursors. Condensation of 1 equiv of thiophene monocarbinol with 1 equiv of substituted aldehyde and 1.5 equiv of pyrrole under refluxing propionic acid conditions followed by alumina column chromatographic purification yielded the desired 22-thiacorroles. Although the corrole formation had been observed with variety of substituted aldehydes, the stable thiacorroles were isolated in 2-3% yields only with 4- and 3-nitrobenzaldehydes. The stable thiacorroles were obtained only under harsh propionic acid conditions and any other mild reaction conditions did not yield 22-thiacorroles. The structure of thiacorroles were unambiguously established using mass, and ID and 2D NMR spectroscopy. The NMR study indicated diminished ring current and distortion of 22-thiacorroles. DFT studies also supported the distortion of thiacorroles. The absorption spectra showed reduction in number of absorption bands and fluorescence study indicated that 22-thiacorroles are weakly fluorescent. The electrochemical studies indicated that 22-thiacorroles undergo easier reductions compared to thiaporphyrins.

  DOI：

  10.1021/jo100607t
• 作为产物：
  描述：

  3,4-二甲氧基噻吩 、 对甲基苯甲醛 在 正丁基锂 、 四甲基乙二胺 、 水 、 氯化铵 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 2.0h， 以55%的产率得到2-[α-(p-tolyl)-α-hydroxymethyl]-3,4-(dimethoxy)-thiophene
  参考文献：
  名称：

  Synthesis and Studies of Thiacorroles

  摘要：

  The first examples of stable 22-thiacorroles containing a direct pyrrole pyrrole bond were synthesized using thiophene monocarbinols as key precursors. Condensation of 1 equiv of thiophene monocarbinol with 1 equiv of substituted aldehyde and 1.5 equiv of pyrrole under refluxing propionic acid conditions followed by alumina column chromatographic purification yielded the desired 22-thiacorroles. Although the corrole formation had been observed with variety of substituted aldehydes, the stable thiacorroles were isolated in 2-3% yields only with 4- and 3-nitrobenzaldehydes. The stable thiacorroles were obtained only under harsh propionic acid conditions and any other mild reaction conditions did not yield 22-thiacorroles. The structure of thiacorroles were unambiguously established using mass, and ID and 2D NMR spectroscopy. The NMR study indicated diminished ring current and distortion of 22-thiacorroles. DFT studies also supported the distortion of thiacorroles. The absorption spectra showed reduction in number of absorption bands and fluorescence study indicated that 22-thiacorroles are weakly fluorescent. The electrochemical studies indicated that 22-thiacorroles undergo easier reductions compared to thiaporphyrins.

  DOI：

  10.1021/jo100607t

文献信息

• Synthesis and Studies of Thiacorroles
  作者：Vijayendra S. Shetti、Uday R. Prabhu、Mangalampalli Ravikanth

  DOI：10.1021/jo100607t

  日期：2010.6.18

  The first examples of stable 22-thiacorroles containing a direct pyrrole pyrrole bond were synthesized using thiophene monocarbinols as key precursors. Condensation of 1 equiv of thiophene monocarbinol with 1 equiv of substituted aldehyde and 1.5 equiv of pyrrole under refluxing propionic acid conditions followed by alumina column chromatographic purification yielded the desired 22-thiacorroles. Although the corrole formation had been observed with variety of substituted aldehydes, the stable thiacorroles were isolated in 2-3% yields only with 4- and 3-nitrobenzaldehydes. The stable thiacorroles were obtained only under harsh propionic acid conditions and any other mild reaction conditions did not yield 22-thiacorroles. The structure of thiacorroles were unambiguously established using mass, and ID and 2D NMR spectroscopy. The NMR study indicated diminished ring current and distortion of 22-thiacorroles. DFT studies also supported the distortion of thiacorroles. The absorption spectra showed reduction in number of absorption bands and fluorescence study indicated that 22-thiacorroles are weakly fluorescent. The electrochemical studies indicated that 22-thiacorroles undergo easier reductions compared to thiaporphyrins.