7-(3-hydroxy-4-methoxyphenyl)-10,10-dimethyl-7,9,10,11-tetrahydro-6H,8H-chromeno[4,3-b]chromene-6,8-dione | 1437793-42-4

• 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-(3-hydroxy-4-methoxyphenyl)-10,10-dimethyl-7,9,10,11-tetrahydro-6H,8H-chromeno[4,3-b]chromene-6,8-dione
• CAS: 1437793-42-4
• 化学式: C₂₅H₂₂O₆
• 分子量: 418.446
• InChiKey: QXDMLKOHQVIZOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  31.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  85.97
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  异香兰素 、 4-羟基香豆素 、 5,5-二甲基-1,3-环己二酮 在 nano-silica sulfuric acid 作用下， 以 neat (no solvent) 为溶剂， 以60%的产率得到7-(3-hydroxy-4-methoxyphenyl)-10,10-dimethyl-7,9,10,11-tetrahydro-6H,8H-chromeno[4,3-b]chromene-6,8-dione
  参考文献：
  名称：

  异环香豆素作为新的AChE / BuChE抑制剂：合成和生物学评估

  摘要：

  通过适当的苯甲醛，二甲酮的一锅反应，合成了一系列称为10,11-dihydrochromeno [4,3- b ] chromene -6,8（7 H，9 H）-diones 4a-o的色烯稠合香豆素。在无溶剂条件下，在纳米二氧化硅硫酸存在下和4-羟基香豆素的收率很高。体外抗胆碱酯酶测定显示3-羟苯基类似物4e对乙酰胆碱酯酶和丁酰胆碱酯酶均显示出最高的抑制活性，具有IC 50值分别为3.28和2.19 µM。结构-活性关系研究表明，通过在3-羟基苯基侧基的对位引入第二个羟基或甲氧基取代基可以调节乙酰胆碱酯酶对丁酰胆碱酯酶的选择性。化合物4e与乙酰胆碱酯酶的对接研究证实了香豆素部分与Trp279之间的π - π堆积相互作用以及羟基与Asn85之间的氢键形成。

  DOI：

  10.1007/s00044-016-1626-7

文献信息

• Chickpea Leaf Exudates: A Highly Efficient Natural Brønsted Acidic Medium for the Synthesis of Pyran-annulated Heterocycles
  作者：Snehali R. Mali、Suresh S. Patil、Sachinkumar K. Shinde、Bhagyashree M. Patil、Rupesh C. Patil

  DOI：10.2174/1570178618666211027104037

  日期：2022.8

  We reported Chickpea leaf exudates (CLEs) as a Brønsted acid, naturally available biodegradable, eco-friendly, and reusable reaction medium for highly efficient and facile one-pot synthesis of pyran-annulated heterocyclic systems, like 7-aryl-benzopyrano[4,3-b]benzopyran-6,8- diones,tetrahydrobenzo[b]pyran, and dihydropyrano[c]chromenes scaffolds. The analogous products were obtained via tandem Knoevengel-Michael addition and cyclo condensation reaction in ethanol at room temperature with 90-96% yields in a short reaction time. Moreover, the reaction media containing Bronsted acids can be easily recovered and reused up to five times, slightly decreasing product yields.

  摘要：我们报道了鹰嘴豆叶渗出物（CLEs）作为一种Brønsted酸，是一种天然可生物降解、环保、可重复使用的反应介质，用于高效而容易的一锅法合成吡喃环并杂环系统，如7-芳基苯并吡喃[4,3-b]苯并吡喃-6,8-二酮、四氢苯并[b]吡喃和二氢吡喃[c]色烷骨架。类似的产物通过在室温下在乙醇中串联Knoevengel-Michael加成和环缩合反应获得，收率为90-96％，反应时间短。此外，含有Brønsted酸的反应介质可以轻松回收和重复使用多达五次，略微降低产物收率。
• 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.