6-hydroxy-9-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one | 221349-05-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-hydroxy-9-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one
• 英文别名: 6-hydroxy-9-(2-hydroxy-4,4-dimethyl-6-oxocyclohexen-1-yl)-3,3-dimethyl-4,9-dihydro-2H-xanthen-1-one
• CAS: 221349-05-9
• 化学式: C₂₃H₂₆O₅
• 分子量: 382.456
• InChiKey: FVQXHVCJKBUEJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 、 2,4-二羟基苯甲醛 在 L-脯氨酸 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以85%的产率得到6-hydroxy-9-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one
  参考文献：
  名称：

  l-Proline-accelerated, eco-friendly synthesis of 9-substituted-2,3,4,9-tetrahydro-1H-xanthen-1-ones under mild conditions

  摘要：

  摘要 通过将二酮或1,3-环己烷二酮与取代的水杨 aldehyde 在温和反应条件下进行一锅缩合，实现了高效的 l-脯氨酸加速合成 9-取代-2,3,4,9-四氢-1H-香豆素-1-酮衍生物。该方案显示出若干显著优势，包括操作简单、反应时间短、环保条件、不需要提取和色谱纯化步骤以及高产率的目标产品。 补充材料： 本文章的补充材料作为单独文件提供：mmc1.doc

  DOI：

  10.1016/j.crci.2013.05.011

文献信息

• Diethylamine-catalyzed environmentally benign synthesis of 1-oxo-hexahydroxanthenes and bis-coumarins at ambient temperature
  作者：Ravindra V. Kupwade、Kapil S. Pandit、Uday V. Desai、Makarand A. Kulkarni、Prakash P. Wadgaonkar

  DOI：10.1007/s11164-016-2464-4

  日期：2016.7

  environmentally benign protocol has been described for one-pot synthesis of 1-oxo-hexahydroxanthenes by pseudo three-component condensation between salicylaldehydes and dimedone, cyclohexane-1,3-dione or 5-methyl cyclohexane-1,3-dione using diethylamine as the catalyst. Based upon the mechanism of the reaction, the protocol has been extended towards the synthesis of tetraketones and bis-coumarins. Graphical Abstract

  摘要 已经描述了通过水杨醛与二甲酮，环己烷-1,3-二酮或5-甲基环己烷-1,3之间的假三组分缩合一锅合成1-氧代-六氢氧杂蒽的极其简单，经济和环境友好的方案。 -使用二乙胺作为催化剂的二酮。根据反应机理，该方案已扩展到四酮和双香豆素的合成。 图形概要
• A green protocol for catalyst-free synthesis of 1-oxo-hexahydroxanthenes in aqueous medium
  作者：D.M. Pore、T.S. Shaikh、K.A. Undale、D.S. Gaikwad

  DOI：10.1016/j.crci.2010.06.015

  日期：2010.12

  Résumé An efficient and eco-friendly synthesis of 1-oxo-hexahydroxanthenes has been expediently accomplished by a reaction of salicylaldehyde with cyclohexane-1,3-dione or dimedone in water as universal solvent at reflux condition without a catalyst. Excellent yields of the products, operational simplicity, simple work-up and catalyst-free synthesis are attractive features of this green protocol.

  摘要 一种高效且环保的1-氧代六氢荧蒽的合成方法已通过在水中以环己烷-1,3-二酮或二美酮与水杨醛反应，在回流条件下无催化剂成功实现。该绿色方法的优点包括高产率、操作简便、简单的后处理以及无催化剂的合成。
• A rapid and efficient CsF catalyzed tandem Knoevenagel–Michael reaction
  作者：Khalid Mohammed Khan、Imran Khan、Shahnaz Perveen、Muhammad Imran Malik

  DOI：10.1016/j.jfluchem.2013.11.010

  日期：2014.2

  A simple, experimentally rapid and efficient CsF catalyzed tandem Knoevenagel-Michael reaction protocol is developed for the synthesis of a series of functionalized 9-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one (1-7) by reacting dimedone with substituted salicylaldehydes. The use of CsF as a catalyst allowed reactions under moderate conditions and resulted in better yields. (C) 2013 Elsevier B.V. All rights reserved.