(Z)-4-(benzo[b]thiophen-3-ylmethylene)-2-phenyl-4H-oxazol-5-one | 35523-49-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-4-(benzo[b]thiophen-3-ylmethylene)-2-phenyl-4H-oxazol-5-one
• 英文别名: (4Z)-4-(1-benzothiophen-3-ylmethylidene)-2-phenyl-1,3-oxazol-5-one
• CAS: 35523-49-0
• 化学式: C₁₈H₁₁NO₂S
• 分子量: 305.357
• InChiKey: AVGDAEKIYMPBGC-GDNBJRDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.66
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (Z)-4-(benzo[b]thiophen-3-ylmethylene)-2-phenyl-4H-oxazol-5-one 、 甲醇 在 三乙胺 作用下， 反应 2.0h， 以82%的产率得到methyl (Z)-2-benzamido-3-(1-benzothiophen-3-yl)prop-2-enoate
  参考文献：
  名称：

  Synthesis and evaluation of new arylbenzo[b]thiophene and diarylthiophene derivatives as inhibitors of the NorA multidrug transporter of Staphylococcus aureus

  摘要：

  The synthesis based on palladium catalytic coupling of 38 new-arylated benzo[b]thiophenes or thiophenes is described in a few steps. We also report the direct arylation of the position 3 of the benzo[b]thiophenic structure, a 'one pot' 2,5-heterodiarylation of thiophenes as well as the synthesis of precursors of amino-acids with a 2-arylated benzo[b]thiophene core. These compounds were evaluated on bacteria strains: most of them did not exhibit any antibiotic activity but were found to selectively inhibit the NorA multidrug transporter of Staphylococcus aureus. As such, they restored the activity of the NorA substrates ciprofloxacin against a resistant S. aureus strain in which this efflux pump is over-expressed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.04.023
• 作为产物：
  描述：

  马尿酸 、 3-甲醛苯并噻吩 在 三乙胺硫酸盐 作用下， 反应 0.48h， 以96%的产率得到(Z)-4-(benzo[b]thiophen-3-ylmethylene)-2-phenyl-4H-oxazol-5-one
  参考文献：
  名称：

  [Et₃NH][HSO₄]-mediated functionalization of hippuric acid: an unprecedented approach to 4-arylidene-2-phenyl-5(4H)-oxazolones

  摘要：

  简便、可持续和经济的合成埃伦迈尔酰胺。

  DOI：

  10.1039/c5ra09290f

文献信息

• Stereoselective Synthesis of 1,3-Diaminotruxillic Acid Derivatives: An Advantageous Combination of CH-<i>ortho</i> -Palladation and On-Flow [2+2]-Photocycloaddition in Microreactors
  作者：Elena Serrano、Alberto Juan、Angel García-Montero、Tatiana Soler、Francisco Jiménez-Márquez、Carlos Cativiela、M. Victoria Gomez、Esteban P. Urriolabeitia

  DOI：10.1002/chem.201503742

  日期：2016.1.4

  The stereoselective synthesis of ε‐isomers of dimethyl esters of 1,3‐diaminotruxillic acid in three steps is reported. The first step is the ortho‐palladation of (Z)‐2‐aryl‐4‐aryliden‐5(4H)‐oxazolones 1 to give dinuclear complexes 2 with bridging carboxylates. The reaction occurs through regioselective activation of the ortho‐CH bond of the 4‐arylidene ring in carboxylic acids. The second step is

  报道了三步法合成1,3-二氨基苯甲酸的二甲酯的ε-异构体的立体选择性合成。第一步是在邻位的（-palladation Ž）-2-芳基-4- aryliden-5（4 ħ）-oxazolones 1，得到双核配合物2具有桥接羧酸盐。发生该反应通过的区域选择性激活邻-C 在羧酸的4-亚芳基环上的H键。第二个步骤是恶唑酮骨架的环外CC键的在[2 + 2] -photocycloaddition 2，得到相应的双核邻-palladated环丁烷3。通过在流动微反应器中使用具有不同波长（465、525或625 nm）的LED光源，可以非常有效地执行此关键步骤。最后一步涉及在甲醇中加氢使3脱钯，得到单异构体ε-1,3-二氨基truxillicic酸衍生物。