3-(4-Methoxy-benzo[b]thiophen-5-yl)-5-phenyl-isoxazole | 864745-81-3

• 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: 3-(4-Methoxy-benzo[b]thiophen-5-yl)-5-phenyl-isoxazole
• 英文别名: 3-(4-Methoxy-1-benzothiophen-5-yl)-5-phenyl-1,2-oxazole；3-(4-methoxy-1-benzothiophen-5-yl)-5-phenyl-1,2-oxazole
• CAS: 864745-81-3
• 化学式: C₁₈H₁₃NO₂S
• 分子量: 307.373
• InChiKey: RIJOMYJYCBUFGB-UHFFFAOYSA-N

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：

  3-(4-Methoxy-benzo[b]thiophen-5-yl)-5-phenyl-isoxazole 在 镍 氢气 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 生成 (Z)-3-Imino-3-(4-methoxy-benzo[b]thiophen-5-yl)-1-phenyl-propen-1-ol
  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 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 盐酸羟胺 、 chloroamine-T 、 pyridinium chlorochromate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 3-(4-Methoxy-benzo[b]thiophen-5-yl)-5-phenyl-isoxazole
  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.