2,4-dimethyl-2,4-di(thiophen-3-yl)pentan-3-one | 956473-45-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2,4-dimethyl-2,4-di(thiophen-3-yl)pentan-3-one
• 英文别名: 2,4-Dimethyl-2,4-di(thien-3-yl)pentan-3-one
• CAS: 956473-45-3
• 化学式: C₁₅H₁₈OS₂
• 分子量: 278.439
• InChiKey: QOYNPSVOHUTODU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  73.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4-dimethyl-2,4-di(thiophen-3-yl)pentan-3-one 反应 12.0h， 生成 3-(2,3-dimethyl-3-(thiophen-3-yl)butan-2-yl)thiophene
  参考文献：
  名称：

  Photodecarbonylation of 1,3-Dithiophenyl Propanone:  Using Nanocrystals to Overcome the Filtering Effect of Highly Absorbing Trace Impurities

  摘要：

  Irradiation of crystalline 2,4-dimethyl-2,4-di(thiophen-3-yl)pentan-3-one (1) resulted in photodecarbonylation and radical combination to give 2 with >99% selectivity. However, extended irradiation led to no more than ca. 8% conversion due to highly absorbing unidentified trace impurities that act as filters. We report here a simple procedure to improve the reaction efficiency by taking advantage of nanocrystalline suspensions prepared by the reprecipitation method, which leads to shorter reaction times and quantitative yields.

  DOI：

  10.1021/ol702000s
• 作为产物：
  描述：

  1,3-di(thiophen-3-yl)propan-2-one 、 碘甲烷 在 乙酸乙酯 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到2,4-dimethyl-2,4-di(thiophen-3-yl)pentan-3-one
  参考文献：
  名称：

  1,3-杂环取代芳香酮的制备方法及应用

  摘要：

  1,3‑杂环取代芳香酮的制备方法及应用，属于医药技术及光电材料领域。本发明以杂环取代的芳香苯乙酸为原料和DCC和DMAP在二氯甲烷体系反应得到化合物，化学物使用柱层析提纯得到最终产品，该产品可以用在降糖药和光电结晶导体材料的制备。本发明使用杂环取代的芳香苯乙酸反应制备1,3‑杂环取代芳香酮；反应操作简单易行，在温和反应条件下进行。本发明提供的合成方法简单易行、科学合理、绿色环保、经济实用，适合规模化生产。

  公开号：

  CN109970703A

文献信息

• Unexpected Solid-State Photochemistry of an α-Thiophenyl-α‘-Thiophenyl-<i>S</i>,<i>S</i>-dioxo-Substituted Ketone
  作者：Marino J. E. Resendiz、Jennifer Taing、Saeed I. Khan、Miguel A. Garcia-Garibay

  DOI：10.1021/jo702127g

  日期：2008.1.1

  Samples of 2,4-dimethyl-2-(thiophen-3-yl)-4-(thiophen-3-yl-S,S-dioxo)pentan-3-one 2 were obtained by controlled MCPBA oxidation of 2,4-dimethyl-2,4-di(thiophen-3-yl)pentan-3-one 1. Rather than the expected photodecarbonylation, UV-vis irradiation of 2 led to the intramolecular 2 + 2 photocycloaddition product 5 in quantitative yields (by GC and NMR) both in solution and in crystalline solid state. Detailed X-ray powder diffraction analyses revealed that the solid-state reaction of sulfone 2 occurs with a loss of long-range order despite retaining some birefringence under polarized microscopy.