4-methoxybenzofuran-5-carbaldehyde oxime

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 4-methoxybenzofuran-5-carbaldehyde oxime
• 英文别名: (NE)-N-[(4-methoxy-1-benzofuran-5-yl)methylidene]hydroxylamine
• 化学式: C₁₀H₉NO₃
• 分子量: 191.186
• InChiKey: AQGFSCJYTNVLNT-IZZDOVSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methoxybenzofuran-5-carbaldehyde oxime 在 镍 氢气 、 chloroamine-T 、 silica gel 、 溶剂黄146 、 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 、 水 为溶剂， 反应 51.0h， 生成 pongamol
  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：

  methyl 4-methoxybenzofuran-5-carboxylate 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 盐酸羟胺 、 pyridinium chlorochromate 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 4-methoxybenzofuran-5-carbaldehyde oxime
  参考文献：
  名称：

  Synthesis of novel benzofuran isoxazolines as protein tyrosine phosphatase 1B inhibitors

  摘要：

  PTPases are considered to be involved in the etiology of diabetes mellitus and neural diseases, such as Alzheimer's disease and Parkinson's disease. Therefore, PTPase inhibitors should be useful tools to Study the role of PTPases in these diseases and other biological phenomena, and which can be developed into chemotherapeutic agents. In the present study, we have synthesized novel benzofuran isoxazolines 13-21 via 1,3-dipolar cycloaddition reaction using karanjin (1) and kanjone (2), isolated from Pongamia pinnata fruits. All the synthesized compounds were evaluated against PTPase enzyme. Compounds 19 and 20 displayed significant inhibitory activity with IC50 values 76 and 81 mu M, respectively. (C) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2006.01.062

文献信息

• Synthesis of novel benzofuran isoxazolines as protein tyrosine phosphatase 1B inhibitors
  作者：Ghufran Ahmad、Pushpesh K. Mishra、Prasoon Gupta、Prem P. Yadav、Priti Tiwari、Akhilesh K. Tamrakar、Arvind K. Srivastava、Rakesh Maurya

  DOI：10.1016/j.bmcl.2006.01.062

  日期：2006.4

  PTPases are considered to be involved in the etiology of diabetes mellitus and neural diseases, such as Alzheimer's disease and Parkinson's disease. Therefore, PTPase inhibitors should be useful tools to Study the role of PTPases in these diseases and other biological phenomena, and which can be developed into chemotherapeutic agents. In the present study, we have synthesized novel benzofuran isoxazolines 13-21 via 1,3-dipolar cycloaddition reaction using karanjin (1) and kanjone (2), isolated from Pongamia pinnata fruits. All the synthesized compounds were evaluated against PTPase enzyme. Compounds 19 and 20 displayed significant inhibitory activity with IC50 values 76 and 81 mu M, respectively. (C) 2006 Published by Elsevier Ltd.
• 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.