7-(4-nitro-phenyl)-7,9,10,11-tetrahydro-chromeno[4,3-b]chromene-6,8-dione | 95223-69-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-(4-nitro-phenyl)-7,9,10,11-tetrahydro-chromeno[4,3-b]chromene-6,8-dione
• 英文别名: 7-(4-nitrophenyl)-7,9,10,11-tetrahydro-6H,8H-chromeno[4,3-b]chromene-6,8-dione；3,4-Benzo-5,6,7,8-tetrahydro-9-(4-nitro-phenyl)-2-oxa-xanthen-dion-(1,8)；9,10-dihydro-7-(4-nitrophenyl)-7H,11H-benzopyrano[3,2-c]chromene-6,8-dione；7-(4-Nitrophenyl)-7,9,10,11-tetrahydrochromeno[3,2-c]chromene-6,8-dione
• CAS: 95223-69-1
• 化学式: C₂₂H₁₅NO₆
• 分子量: 389.364
• InChiKey: JLRYTXOEHBALQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-羟基香豆素 、 1,3-环己二酮 、 对硝基苯甲醛 以 溶剂黄146 为溶剂， 反应 5.0h， 以75%的产率得到7-(4-nitro-phenyl)-7,9,10,11-tetrahydro-chromeno[4,3-b]chromene-6,8-dione
  参考文献：
  名称：

  新型苯并吡喃并[3,2-c]色烯-6,8-二酮衍生物的合成及细胞毒活性

  摘要：

  4-羟基香豆素构成许多天然产物，药物和农药的结构核。最近报道了新的合成香豆素家族的有前途的生物学特性。因此，进行了新的苯并吡喃并[3,2-c]亚甲基-6,8-二酮的有效合成，并通过红外，质谱，1 H-NMR和C，H，N分析确认了15种化合物的结构。然后，在四种不同的人类癌细胞系（Raji，HeLa，LS180和MCF-7）上评估了这些化合物的细胞毒活性。结果表明，这些化合物具有弱至中度的抗肿瘤活性，其IC 50为49至100μM以上。在化合物9,10-二氢-7-（3-甲氧基苯基）-7 H，11 H-苯并吡喃并[3,2-c]色烯-6,8-二酮[ 4k ]表现出最高的活性。此外，构象分析表明邻位取代基明显不同于间位和对位取代基。

  DOI：

  10.1007/s00044-010-9340-3

文献信息

• New method for the synthesis of chromeno[4,3-b]chromene derivatives via multicomponent reaction promoted by niobium pentachloride
  作者：Willian Henrique dos Santos、Luiz Carlos da Silva-Filho

  DOI：10.1016/j.tetlet.2017.01.062

  日期：2017.3

  Chromeno[4,3-b]chromene derivatives were synthesized from multicomponent reaction between 4-hydroxycoumarin, aryl aldehyde derivatives and 1,3-cyclohexanedione promoted by niobium pentachloride. This new method is simple, cost-effective, provides good yields with good substrate generality and can be conducted in short reaction times.

  由五氯化铌促进的4-羟基香豆素，芳基醛衍生物与1,3-环己二酮之间的多组分反应合成了铬诺[4,3-b]色烯衍生物。该新方法简单，经济高效，具有良好的底物通用性，产率高且可以在较短的反应时间内进行。
• Fe(DS)3, an efficient Lewis acid-surfactant-combined catalyst (LASC) for the one pot synthesis of chromeno[4,3-b]chromene derivatives by assembling the basic building blocks
  作者：Koyel Pradhan、Sanjay Paul、Asish R. Das

  DOI：10.1016/j.tetlet.2013.04.001

  日期：2013.6

  A highly efficient multicomponent heteroannulation protocol for the synthesis of a library of chromeno[4,3-b]chromene derivative has been developed by applying a Lewis acid-surfactant-combined catalyst (LASC) [Fe(DS)(3)]. The LASC converted the initially floating reaction mass into a homogeneous mixture, which on stirring became a turbid emulsion of colloidal aggregates. The shape and size of the colloidal aggregates are confirmed by optical microscopy and DLS. The aqueous reaction medium, dual role of the catalyst in aqueous media, easy recovery of the catalyst, and high yield make the protocol attractive, sustainable, and economical. (C) 2013 Elsevier Ltd. All rights reserved.
• Catalytic Method for Synthesis of Benzopyrano[3,2-c]chromene-6,8-dione Derivatives by Heteropoly Acids
  作者：Radineh Motamedi、Saeede Baghbani、Fatemeh F. Bamoharram

  DOI：10.1080/00397911.2010.542536

  日期：2012.6

  Benzopyrano[3,2-c]chromene-6,8-dione derivatives were prepared by a three-component one-pot cyclocondensation of 4-hyroxycoumarin, aldehydes, and 1,3, cyclohexadione using a catalytic amount of heteropolyacids in boiling ethanol in very good yields and rates.
• Synthesis and cytotoxic activity of novel benzopyrano[3,2-c]chromene-6,8-dione derivatives
  作者：Abbas Shafiee、Radineh Motamedi、Omidreza Firuzi、Savis Meili、Ahmad Reza Mehdipour、Ramin Miri

  DOI：10.1007/s00044-010-9340-3

  日期：2011.5

  efficient synthesis of new benzopyrano[3,2-c]chromene-6,8-dione was undertaken and the structures of 15 compounds were confirmed by their IR, Mass, 1H-NMR, and C, H, N analysis. Then, the cytotoxic activities of these compounds were assessed on four different human cancer cell lines (Raji, HeLa, LS180, and MCF-7). The results showed that these compounds had weak-to-moderate antitumoral activities and their

  4-羟基香豆素构成许多天然产物，药物和农药的结构核。最近报道了新的合成香豆素家族的有前途的生物学特性。因此，进行了新的苯并吡喃并[3,2-c]亚甲基-6,8-二酮的有效合成，并通过红外，质谱，1 H-NMR和C，H，N分析确认了15种化合物的结构。然后，在四种不同的人类癌细胞系（Raji，HeLa，LS180和MCF-7）上评估了这些化合物的细胞毒活性。结果表明，这些化合物具有弱至中度的抗肿瘤活性，其IC 50为49至100μM以上。在化合物9,10-二氢-7-（3-甲氧基苯基）-7 H，11 H-苯并吡喃并[3,2-c]色烯-6,8-二酮[ 4k ]表现出最高的活性。此外，构象分析表明邻位取代基明显不同于间位和对位取代基。