5-(4-Methoxy-1-benzothiophen-5-yl)-3-phenyl-1,2-oxazole | 864745-76-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 5-(4-Methoxy-1-benzothiophen-5-yl)-3-phenyl-1,2-oxazole
• 英文别名: 5-(4-methoxy-1-benzothiophen-5-yl)-3-phenyl-1,2-oxazole
• CAS: 864745-76-6
• 化学式: C₁₈H₁₃NO₂S
• 分子量: 307.373
• InChiKey: KNHZHZMNRFVCKB-UHFFFAOYSA-N

物化性质

• 沸点：
  485.9±40.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  63.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-Methoxy-1-benzothiophen-5-yl)-3-phenyl-1,2-oxazole 在 镍 氢气 、 silica gel 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 34.0h， 生成 (Z)-3-hydroxy-1-(4-methoxybenzothiophen-5-yl)-3-phenyl-prop-2-en-1-one
  参考文献：
  名称：

  An efficient route for commercially viable syntheses of furan- and thiophene-anellated β-hydroxychalcones

  摘要：

  An efficient route for the syntheses of beta-hydroxychalcones containing benzofuran and benzothiophene rings is described. Isoxazolines obtained from oxime-olefin cycloadditions were reduced under pressure to a mixture of products. Isoxazoles obtained from Claisen aroylation of an ester and subsequent acid cyclization, or from isoxazolines via DDQ-mediated dehydrogenation, were subjected to catalytic hydrogenation followed by hydrolysis to afford 1-phenyl-3-(benzofuran-5-yl)-1,3-diketone and 1-phenyl-3(benzothiophene-5-yl)-1,3-diketones in very good yields. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.111
• 作为产物：
  描述：

  4-methoxybenzo[b]thiophene-5-carboxylic acid methyl ester 、 (E)-1-phenylethanone oxime 在 正丁基锂 、 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.75h， 以92%的产率得到5-(4-Methoxy-1-benzothiophen-5-yl)-3-phenyl-1,2-oxazole
  参考文献：
  名称：

  An efficient route for commercially viable syntheses of furan- and thiophene-anellated β-hydroxychalcones

  摘要：

  An efficient route for the syntheses of beta-hydroxychalcones containing benzofuran and benzothiophene rings is described. Isoxazolines obtained from oxime-olefin cycloadditions were reduced under pressure to a mixture of products. Isoxazoles obtained from Claisen aroylation of an ester and subsequent acid cyclization, or from isoxazolines via DDQ-mediated dehydrogenation, were subjected to catalytic hydrogenation followed by hydrolysis to afford 1-phenyl-3-(benzofuran-5-yl)-1,3-diketone and 1-phenyl-3(benzothiophene-5-yl)-1,3-diketones in very good yields. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.111

文献信息

• An efficient route for commercially viable syntheses of furan- and thiophene-anellated β-hydroxychalcones
  作者：Prem P. Yadav、Ghufran Ahmad、Rakesh Maurya

  DOI：10.1016/j.tetlet.2005.06.111

  日期：2005.8

  An efficient route for the syntheses of beta-hydroxychalcones containing benzofuran and benzothiophene rings is described. Isoxazolines obtained from oxime-olefin cycloadditions were reduced under pressure to a mixture of products. Isoxazoles obtained from Claisen aroylation of an ester and subsequent acid cyclization, or from isoxazolines via DDQ-mediated dehydrogenation, were subjected to catalytic hydrogenation followed by hydrolysis to afford 1-phenyl-3-(benzofuran-5-yl)-1,3-diketone and 1-phenyl-3(benzothiophene-5-yl)-1,3-diketones in very good yields. (c) 2005 Elsevier Ltd. All rights reserved.