Spirobiphthalide | 80716-35-4

• 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: Spirobiphthalide
• 英文别名: Spiro-3,3'-dione；(±)-3H,3'H-spiro[benzofuran-2,1'-isobenzofuran]-3,3'-dione；3H,3'H-spiro[benzofuran-2,1'-isobenzofuran]-3,3-dione；Spiro[1-benzofuran-2,3'-2-benzofuran]-1',3-dione
• CAS: 80716-35-4
• 化学式: C₁₅H₈O₄
• 分子量: 252.226
• InChiKey: CCGBTDNOKIPMJU-UHFFFAOYSA-N

物化性质

• 沸点：
  523.5±50.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 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：
  4

反应信息

• 作为反应物：
  描述：

  Spirobiphthalide 在 溶剂黄146 、 锌 作用下， 以67 %的产率得到benzofuroisocoumarin
  参考文献：
  名称：

  通过将 3-磺酰苯酞加成到 2-甲酰芳基三氟甲磺酸酯并转化为苯并呋喃异香豆素，合成螺内酯和功能化苯并呋喃

  摘要：

  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。

  DOI：

  10.1021/acs.joc.2c03097
• 作为产物：
  描述：

  N,N-二乙基-2-甲基苯甲酰胺 在 三氟化硼乙醚 、 甲基磺酰氯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 生成 Spirobiphthalide
  参考文献：
  名称：

  The Synthesis of Wrightiadionevia Directed Remote Metalation

  摘要：

  报道了采用N,N-二乙基羧酰胺作为导向金属化基团（DMG）和亲电基团，通过定向远程金属化（DreM）和亲电取代反应合成wrightiadione。N,N-二乙基异黄酮-2′-羧酰胺与LDA进行锂化反应，在C-2位生成碳负离子并进一步环化形成wrightiadione。

  DOI：

  10.1055/s-2003-39313

文献信息

• Hypervalent-Iodine-Mediated Cascade Annulation of Diarylalkynes Forming Spiro Heterocycles under Metal-Free Conditions
  作者：Xiang Zhang、Chao Yang、Daisy Zhang-Negrerie、Yunfei Du

  DOI：10.1002/chem.201406393

  日期：2015.3.23

  unusual reaction featuring the cascade annulation of internal alkynes to afford spiro heterocycles as the products has been realized for the first time with a hypervalent iodine reagent as the only oxidant. This unprecedented process encompasses not only two sequential CN/CO‐bond formations, but also the insertion of a carbonyl oxygen, all in one pot under metal‐free conditions.

  以高价碘试剂为唯一氧化剂，首次实现了一种不寻常的反应，该反应具有内部炔烃的级联环化作用以提供螺环杂环产物的作用。这个过程前所未有不仅包括两个顺序Ç  N / C 在不含金属的条件下一锅O型键的形成，而且还一个羰基氧的插入，所有。
• 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.
• Synthesis of molecules with fused blocked aromatic rings
  作者：Bernard Miller、Ajit K. Bhattacharya

  DOI：10.1016/s0040-4039(01)82011-6

  日期：1981.1
• First synthesis of spiro[benzofuran-2,1′-isobenzofuran]-3,3′-dione and its X-ray crystal structure
  作者：Roy M. Letcher、Nai-Chiu Kwok、Kung-Kai Cheung

  DOI：10.1039/p19920001769

  日期：——

  The title compound has been synthesised by selenium dioxide oxidation of 2'-carboxy-2-hydroxydeoxybenzoin 3 and its structure has been confirmed spectroscopically and by X-ray crystallography. An earlier report of this compound's synthesis is shown to be erroneous. The synthesis of 3-(2-hydroxyphenyl)isoquinolin-1(2H)-ones from 2'-carboxy-2-hydroxydeoxybenzoin 3 is also described.
• MILLER, B.;BHATTACHARYA, AJIT, K., TETRAHEDRON LETT., 1981, 22, N 38, 3753-3756
  作者：MILLER, B.、BHATTACHARYA, AJIT, K.

  DOI：——

  日期：——