2-(3-thienyl)-3H-benzofuro[3,2-e]benzofuran | 1454601-09-2

• 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: 2-(3-thienyl)-3H-benzofuro[3,2-e]benzofuran
• 英文别名: 2-(3-Thienyl)benzofuro[5,4-b]benzofuran；2-thiophen-3-yl-[1]benzofuro[3,2-e][1]benzofuran
• CAS: 1454601-09-2
• 化学式: C₁₈H₁₀O₂S
• 分子量: 290.342
• InChiKey: VEHQAOYLMIXRLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  二苯并[b,d]呋喃-2-甲醛 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 一氯化碘 、 溶剂黄146 、 三乙胺 、 间氯过氧苯甲酸 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 2-(3-thienyl)-3H-benzofuro[3,2-e]benzofuran
  参考文献：
  名称：

  Design, synthesis and antitubercular evaluation of novel 2-substituted-3H-benzofuro benzofurans via palladium–copper catalysed Sonagashira coupling reaction

  摘要：

  A series of novel natural product like 2-substiuted-3H-benzofurobenzofurans designed by molecular hybridization were synthesized in very good yields. The key reactions involved in the synthesis are iodination of 2-dibenzofuranol using iodine monochloride followed by palladium-copper catalyzed Sonagashira-coupling of 1-iododibenzofuran-2-ol with various alkyl and aryl acetylenes. Among the all 10 new compounds screened for in vitro anti-mycobacterial activity against Mycobacterium tuberculosis H37Rv, 2-(4-methoxy-2-methyl phenyl)-3H-benzofuro[3,2-e]benzofuran (7c) was found to be most active with MIC 3.12 mu g/mL and has shown lower cytotoxicity with good therapeutic index. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.048

文献信息

• Design, synthesis and antitubercular evaluation of novel 2-substituted-3H-benzofuro benzofurans via palladium–copper catalysed Sonagashira coupling reaction
  作者：Thirumal Yempala、Jonnalagadda Padma Sridevi、Perumal Yogeeswari、Darmarajan Sriram、Srinivas Kantevari

  DOI：10.1016/j.bmcl.2013.07.048

  日期：2013.10

  A series of novel natural product like 2-substiuted-3H-benzofurobenzofurans designed by molecular hybridization were synthesized in very good yields. The key reactions involved in the synthesis are iodination of 2-dibenzofuranol using iodine monochloride followed by palladium-copper catalyzed Sonagashira-coupling of 1-iododibenzofuran-2-ol with various alkyl and aryl acetylenes. Among the all 10 new compounds screened for in vitro anti-mycobacterial activity against Mycobacterium tuberculosis H37Rv, 2-(4-methoxy-2-methyl phenyl)-3H-benzofuro[3,2-e]benzofuran (7c) was found to be most active with MIC 3.12 mu g/mL and has shown lower cytotoxicity with good therapeutic index. (C) 2013 Elsevier Ltd. All rights reserved.