3-(3,4-dimethoxyphenyl)-2,5-dihydrofuran-2,5-dione | 1236074-41-1

• 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: 3-(3,4-dimethoxyphenyl)-2,5-dihydrofuran-2,5-dione
• 英文别名: 3-(3,4-dimethoxyphenyl)furan-2,5-dione；3-(3,4-Dimethoxyphenyl)furan-2,5-dione
• CAS: 1236074-41-1
• 化学式: C₁₂H₁₀O₅
• 分子量: 234.208
• InChiKey: FYZOFKBYHZQXPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(3,4-dimethoxyphenyl)-2,5-dihydrofuran-2,5-dione 生成
  参考文献：
  名称：

  Synthesis and Pharmacological Characterization of Bicyclic Triple Reuptake Inhibitor 3-Aryl Octahydrocyclopenta[c]pyrrole Analogues

  摘要：

  The present work expands the chemical space known to offer potent inhibition of the serotonin transporter (SERT), norepinephrine transporter (NET), and dopamine transporter (DAT) and discloses novel bicyclic octahydrocyclopenta[c]pyrrole and octahydro-1H-isoindole scaffolds as potent triple reuptake inhibitors (TRIs) for the potential treatment of depression. Optimized compounds 22a (SEAT, NET, DAT, IC(50) = 20, 109, 430 nM), 23a (SERT, NET, DAT, IC(50) = 29, 85, 168 nM), and 26a (SERT, NET, DAT, IC(50) = 53, 150, 140 nM) were highly brain penetrant, active in vivo in the mouse tail suspension test at 10 and 30 mpk PO, and were not generally motor stimulants at doses ranging from 1 to 30 mpk PO. Moderate in vitro cytochrome P450 (CYP) and potassium ion channel Kv11.1 (hERG) inhibition were uncovered as potential liabilities for the chemical series.

  DOI：

  10.1021/jm101312a
• 作为产物：
  描述：

  (Z)-2-(3,4-dimethoxyphenyl)but-2-enedioic acid 在 乙酸酐 作用下， 反应 0.5h， 生成 3-(3,4-dimethoxyphenyl)-2,5-dihydrofuran-2,5-dione
  参考文献：
  名称：

  通过富马酸的Heck芳基化制得的芳基马来酸酐

  摘要：

  发现富马酸与芳基碘化物的钯催化的芳基化是一种非常简单，经济且可扩展的制备芳基马来酸酐的方法。芳基片段上供体部分的存在促进了该反应，并且在强受体基团上不发生该反应。

  DOI：

  10.1016/j.tetlet.2010.05.023

文献信息

• 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。