wrightiadione | 148180-61-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: wrightiadione
• 英文别名: indeno[2,1-b]chromene-6,11-dione；Benz[b]indeno[1,2-e]pyran-6,11-dione
• CAS: 148180-61-4
• 化学式: C₁₆H₈O₃
• 分子量: 248.238
• InChiKey: CXXCRLLJRGEAJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-茚酮 在 pyridinium chlorochromate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 wrightiadione
  参考文献：
  名称：

  THE FIRST SYNTHESIS OF WRIGHTIADIONE

  摘要：

  The first synthesis of tetracyclic isoflavone wrightiadione 1 was achieved through the benzylic oxidation of the key intermediate isoflavone 2 which in turn could be obtained by condensation of 2-indanone with methyl salicylate and LDA.

  DOI：

  10.1081/scc-100104406

文献信息

• The Synthesis of Wrightiadionevia Directed Remote Metalation
  作者：Somsak Ruchirawat、Nopporn Thasana

  DOI：10.1055/s-2003-39313

  日期：——

  The application of directed remote metalation (DreM) and electrophilic substitution is reported for the synthesis of wrightiadione using N,N-diethylcarboxamide as a directed metalation group (DMG) and electrophilic group. The lithiation of N,N-diethylisoflavone-2′-carboxamide with LDA gave a carbanion at C-2 which further cyclized to wrightiadione.

  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。
• An efficient one-pot synthesis of indanone fused heterocyclic compounds via SeO2/FeCl3 promoted intramolecular Friedel-Craft acylation reaction
  作者：Huan Zhang、Qi Wang、Lu Huang、Ziye Tian、Shunguang Zhang、Youlai Zhang

  DOI：10.1016/j.tetlet.2021.153070

  日期：2021.5

  for generating indanone fused heterocyclic compounds which contains a unique tetracyclic isoflavone moiety was developed. This unprecedented one-pot route utilizes a wide spread of substrates through three-step tandem Riley oxidation/Friedel-Crafts reaction/oxidation with SeO2/FeCl3 in moderate yield. Moreover, some of the synthesized heterocyclic compounds have shown moderate anticancer activities

  茚满酮已显示出广泛的生物活性。开发了一种高效且直接的合成方法，用于生成包含独特的四环异黄酮部分的茚满酮稠合杂环化合物。这种前所未有的一锅法通过中等步骤的三步串联赖利氧化/弗里德尔-克来福特反应/ SeO 2 / FeCl 3氧化利用了广泛的底物。此外，一些合成的杂环化合物显示出中等的抗癌活性。
• Tandem Dehydrogenation/Oxidation/Oxidative Cyclization Approach to Wrightiadione and Its Derivatives
  作者：Yujeong Jeong、Youngtaek Moon、Sungwoo Hong

  DOI：10.1021/acs.orglett.5b01618

  日期：2015.7.2

  Wrightiadione contains a unique tetracyclic isoflavone moiety and has been shown to exhibit a broad range of biological activities. An efficient and Straightforward synthetic method for generating the molecular complexity,of wrightiadione was developed, through three-step tandem dehydrogenation/oxidation/oxidative cyclization reactions with a Pd/Cu. catalytic system. This Unprecedented one-pot route utilizes a broad: range of substrates, providing a convenient and powerful synthetic tool for accessing naturally occurring tetracyclic isoflavone wrightiadione and its nitrogen-containing derivatives.
• Discovery of wrightiadione as a novel template for the TrkA kinase inhibitors
  作者：Yujeong Jeong、Sang Min Lim、Sungwoo Hong

  DOI：10.1016/j.bmcl.2015.09.070

  日期：2015.11

  Enzymatic kinase assays and docking simulation studies have shown that the natural product wrightiadione displays inhibitory activity toward TrkA and PLK3. In this study, the template of wrightiadione served as a starting point for Trk inhibitor development campaigns. Molecular simulation provided structural insights for the design of derivatives that were efficiently generated by our recently developed 3-step tandem synthetic approach, resulting in the discovery of compound 2h with biochemical potency at the single-digit micromolar level. (C) 2015 Elsevier Ltd. All rights reserved.
• An Efficient SeO2/FeCl3 Promoted Acylation:Intramolecular Friedel-Crafts Reaction Leading to a One-Pot Synthesis of Wrightiadione and Its Derivatives
  作者：Shunguang Zhang、Youlai Zhang、Huan Zhang、Qi Wang、Lu Huang、Ziye Tian

  DOI：10.3987/com-21-14423

  日期：——