Spiro[2-benzofuran-3,2'-benzo[g][1]benzofuran]-1,3'-dione | 1430805-64-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: Spiro[2-benzofuran-3,2'-benzo[g][1]benzofuran]-1,3'-dione
• 英文别名: spiro[2-benzofuran-3,2'-benzo[g][1]benzofuran]-1,3'-dione
• CAS: 1430805-64-3
• 化学式: C₁₉H₁₀O₄
• 分子量: 302.286
• InChiKey: PYOZRJLJBNCTJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6b,11b-dihydroxy-6bH-indeno[1,2-b]naphtho[2,1-d]furan-7(11bH)-one 在 solid supported silica sulfuric acid 作用下， 以 neat (no solvent) 为溶剂， 反应 3.0h， 以71%的产率得到Spiro[2-benzofuran-3,2'-benzo[g][1]benzofuran]-1,3'-dione
  参考文献：
  名称：

  Silica sulfuric acid: an efficient reusable heterogeneous solid support for the synthesis of 3H,3′H-spiro[benzofuran-2,1′isobenzofuran]-3,3′-diones under solvent-free condition

  摘要：

  A highly efficient protocol for the library synthesis of biologically important 3H,3'H-spiro[benzofuran-2,1'isobenzofuran]-3,3'-diones has been developed by employing silica sulfuric acid (SSA) as solid acid support under solvent-free condition. The dual characteristics of SSA, as an activating agent as well as oxidizing agent, have been well exposed in these syntheses. The intrinsic advantages of the methodology are the use of solvent-free reaction condition without using any toxic reagents or metal catalyst, operational simplicity, recyclability of the solid support, good availability of the starting materials, and excellent yields which make the method attractive, economic, and 'benign by design'. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.01.109

文献信息

• Efficient synthesis of 3 H ,3′ H -spiro[benzofuran-2,1′-isobenzofuran]-3,3′-dione as novel skeletons specifically for influenza virus type B inhibition
  作者：Yashwardhan Malpani、Raghavendra Achary、So Yeon Kim、Hee Chun Jeong、Pilho Kim、Soo Bong Han、Meehyein Kim、Chong-Kyo Lee、Jae Nyoung Kim、Young-Sik Jung

  DOI：10.1016/j.ejmech.2013.01.015

  日期：2013.4

  An efficient and novel two step synthetic procedure to prepare various substituted 3H,3'H-spiro[benzofuran-2,1'-isobenzofuran]-3,3'-diones A, was established from very simple and easily available starting materials. The developed method is a robust and general approach for the synthesis of these structures. The prepared compounds were tested against influenza virus type A viz., A/Taiwan/1/86 (H1N1), A/Hong Kong/8/68 (H3N2) and type B viz., B/Panama/45/90, B/Taiwan/2/62, B/Lee/40, B/Brisbane/60/2008. Among 31 compounds tested, some of them showed good activity (selective index values >10) against these influenza viruses preferentially for type B. The most active compound 3b showed activity in 3.0-16.1 mu M range with a selectivity index value between 30 and 166 against these type B viruses, in which it was comparable to the antiviral agent favipiravir. Also, 3b is found to be inactive against other enveloped viruses (viz., HIV and HSV) showing its specificity for influenza viruses. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Silica sulfuric acid: an efficient reusable heterogeneous solid support for the synthesis of 3H,3′H-spiro[benzofuran-2,1′isobenzofuran]-3,3′-diones under solvent-free condition
  作者：Kamalesh Debnath、Sudipta Pathak、Animesh Pramanik

  DOI：10.1016/j.tetlet.2014.01.109

  日期：2014.3

  A highly efficient protocol for the library synthesis of biologically important 3H,3'H-spiro[benzofuran-2,1'isobenzofuran]-3,3'-diones has been developed by employing silica sulfuric acid (SSA) as solid acid support under solvent-free condition. The dual characteristics of SSA, as an activating agent as well as oxidizing agent, have been well exposed in these syntheses. The intrinsic advantages of the methodology are the use of solvent-free reaction condition without using any toxic reagents or metal catalyst, operational simplicity, recyclability of the solid support, good availability of the starting materials, and excellent yields which make the method attractive, economic, and 'benign by design'. (C) 2014 Elsevier Ltd. All rights reserved.