6-fluoro-3H,3'H-spiro[benzofuran-2,1'-isobenzofuran]-3,3'-dione | 1430805-83-6

• 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: 6-fluoro-3H,3'H-spiro[benzofuran-2,1'-isobenzofuran]-3,3'-dione
• 英文别名: 6-Fluorospiro[1-benzofuran-2,3'-2-benzofuran]-1',3-dione
• CAS: 1430805-83-6
• 化学式: C₁₅H₇FO₄
• 分子量: 270.217
• InChiKey: PBKXXQBZVKOPLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  7-fluoro-4b,9b-dihydroxy-4bH-indeno[1,2-b]benzofuran-10(9bH)-one 在 碘 作用下， 以 乙醇 为溶剂， 以20%的产率得到6-fluoro-3H,3'H-spiro[benzofuran-2,1'-isobenzofuran]-3,3'-dione
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2013.01.015

文献信息

• Synthesis of Spirolactones and Functionalized Benzofurans via Addition of 3-Sulfonylphthalides to 2-Formylaryl Triflates and Conversion to Benzofuroisocoumarins
  作者：Deepa Nair、Pallabita Basu、Soumyaranjan Pati、Kajal Baseshankar、Chenikkayala Siva Sankara、Irishi N. N. Namboothiri

  DOI：10.1021/acs.joc.2c03097

  日期：——

  modified Hauser–Kraus reaction of 3-sulfonylphthalide with 2-formylaryl triflates is reported here. The initial reaction involved 1,2-addition of phthalide to the formyl group and intramolecular cyclization via substitution of triflate followed by a cascade of rearrangements leading to spirolactone or benzofuran derivatives. The electronic nature of substituents on aryl triflates affected the course

  本文报道了一种通过 3-磺酰苯酞与 2-甲酰芳基三氟甲磺酸酯的改良 Hauser-Kraus 反应合成螺苯并呋喃-异苯并呋喃和取代苯并呋喃的便捷方案。最初的反应涉及苯酞与甲酰基的 1,2-加成和通过取代三氟甲磺酸酯进行分子内环化，随后进行级联重排，生成螺内酯或苯并呋喃衍生物。芳基三氟甲磺酸酯上取代基的电子性质影响了反应的过程和结果。该机制得到了通过质谱法成功表征其中一种中间体的支持。一种药用相关的 B 型流感病毒抑制剂苯并呋喃异香豆素是从螺环化合物一步合成的，从而证明了我们方法的合成效用。