3-(4-methylthiophenyl)-4-(4-methoxyphenyl)-2,5-dihydrofuran-2,5-dione | 1208065-55-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3-(4-methylthiophenyl)-4-(4-methoxyphenyl)-2,5-dihydrofuran-2,5-dione
• 英文别名: 3-(4-Methoxyphenyl)-4-(4-methylsulfanylphenyl)furan-2,5-dione
• CAS: 1208065-55-7
• 化学式: C₁₈H₁₄O₄S
• 分子量: 326.373
• InChiKey: OFINBAFWLFWQHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  77.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-methylthiophenyl)-4-(4-methoxyphenyl)-2,5-dihydrofuran-2,5-dione 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 3-(4-Methoxyphenyl)-4-(4-methylsulfinylphenyl)furan-2,5-dione
  参考文献：
  名称：

  Synthesis and PGE2 production inhibition of 1H-furan-2,5-dione and 1H-pyrrole-2,5-dione derivatives

  摘要：

  3,4-Diphenyl-substituted 1H-furan-2,5-dione and 1H-pyrrole-2,5-dione derivatives were synthesized and evaluated for the inhibitory activities on LPS-induced PGE(2) production in RAW 264.7 macrophage cells. Both 1H-furan-2,5-dione and 1H-pyrrole-2,5-dione rings as main scaffolds were easily obtained using one of three synthetic methods. Among the compounds investigated, 1H-3-(4-sulfamoylphenyl)-4-phenyl-pyrrole-2,5-dione (6l) showed a strong inhibitory activity (IC50 = 0.61 mu M) of PGE(2) production. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.067
• 作为产物：
  描述：

  dimethyl 2-(4-methoxyphenyl)maleate 在 dihydrogen dichloro-bis(di-tert-butylphosphinito-κP)palladium(2-) 、 sodium acetate 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 15.0h， 生成 3-(4-methylthiophenyl)-4-(4-methoxyphenyl)-2,5-dihydrofuran-2,5-dione
  参考文献：
  名称：

  通过 Heck 芳基化快速合成海洋天然产物 Prepolycitrin A 和 Polycitrin A 和 B

  摘要：

  通过使用马来酸酐或富马酸二甲酯与芳基重氮四氟硼酸盐的 Heck-Matsuda 芳基化，开发了用于合成海洋天然产物 prepolycitrin A 以及 polycitrin A 和 B 的新的、有效的方案。对称和不对称的 3,4-二芳基马来酸酐都可以轻松有效地制备。使用三溴异氰脲酸的高效溴化反应提供了获得聚柠檬素家族化合物的途径。在存在酪胺的微波辐射下，相应的马来酰亚胺以高产率从溴化 3,4-二芳基马来酸酐中获得。

  DOI：

  10.1002/ejoc.201301108

文献信息

• Synthesis and PGE2 production inhibition of 1H-furan-2,5-dione and 1H-pyrrole-2,5-dione derivatives
  作者：Jong Taik Moon、Ji Young Jeon、Hang Ah Park、Young-Soo Noh、Kyung-Tae Lee、Jungahn Kim、Dong Joon Choo、Jae Yeol Lee

  DOI：10.1016/j.bmcl.2009.11.067

  日期：2010.1

  3,4-Diphenyl-substituted 1H-furan-2,5-dione and 1H-pyrrole-2,5-dione derivatives were synthesized and evaluated for the inhibitory activities on LPS-induced PGE(2) production in RAW 264.7 macrophage cells. Both 1H-furan-2,5-dione and 1H-pyrrole-2,5-dione rings as main scaffolds were easily obtained using one of three synthetic methods. Among the compounds investigated, 1H-3-(4-sulfamoylphenyl)-4-phenyl-pyrrole-2,5-dione (6l) showed a strong inhibitory activity (IC50 = 0.61 mu M) of PGE(2) production. (C) 2009 Elsevier Ltd. All rights reserved.
• Expeditious Synthesis of the Marine Natural Products Prepolycitrin A and Polycitrins A and B through Heck Arylations
  作者：Karen Canto、Rodrigo da Silva Ribeiro、André F. P. Biajoli、Carlos Roque D. Correia

  DOI：10.1002/ejoc.201301108

  日期：2013.12

  the syntheses of the marine natural products prepolycitrin A as well as polycitrins A and B were developed by employing the Heck–Matsuda arylation of maleic anhydride or dimethyl fumarate with aryldiazonium tetrafluoroborates. Both symmetrical and unsymmetrical 3,4-diarylmaleic anhydrides were easily and effectively prepared. Efficient bromination reactions that employed tribromoisocyanuric acid provided

  通过使用马来酸酐或富马酸二甲酯与芳基重氮四氟硼酸盐的 Heck-Matsuda 芳基化，开发了用于合成海洋天然产物 prepolycitrin A 以及 polycitrin A 和 B 的新的、有效的方案。对称和不对称的 3,4-二芳基马来酸酐都可以轻松有效地制备。使用三溴异氰脲酸的高效溴化反应提供了获得聚柠檬素家族化合物的途径。在存在酪胺的微波辐射下，相应的马来酰亚胺以高产率从溴化 3,4-二芳基马来酸酐中获得。