9-(4-dimethylamino-phenyl)-3,4,5,6,7,9-hexahydro-2H-xanthene-1,8-dione | 113535-16-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 9-(4-dimethylamino-phenyl)-3,4,5,6,7,9-hexahydro-2H-xanthene-1,8-dione
• 英文别名: 9-(4-Dimethylamino-phenyl)-3,4,5,6,7,9-hexahydro-2H-xanthen-1,8-dion；9-(4-Dimethylamino-phenyl)-3,4,5,6,7,9-hexahydro-2H-xanthene-1,8-dione；9-[4-(dimethylamino)phenyl]-3,4,5,6,7,9-hexahydro-2H-xanthene-1,8-dione
• CAS: 113535-16-3
• 化学式: C₂₁H₂₃NO₃
• 分子量: 337.419
• InChiKey: OLJHBJYCJRKHLM-UHFFFAOYSA-N

物化性质

• 沸点：
  549.2±50.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3-环己二酮 在 哌啶 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 0.67h， 生成 9-(4-dimethylamino-phenyl)-3,4,5,6,7,9-hexahydro-2H-xanthene-1,8-dione
  参考文献：
  名称：

  CHLOROSULFONATION OF 9-ARYLOCTAHYDROXANTHEN-1,8-DIONES

  摘要：

  The 9-aryloctathydroxanthen-1,8-diones (3, 4-24) were prepared by reaction of cyclohexan-1,3-dione (1) with selected arylaldehydes. The xanthendiones (4-9, 11, 12, 18, 21, 22) were successfully reacted with chlorosulfonic acid, and the crude sulfonyl chlorides were converted into 15 sulfonamides (26-40) for screening as potential pesticides. Attempted chlorosulfonation of the xanthendiones (13-17) was unsuccessful. alpha-Methylcinnamaldehyde was reacted with cyclohexandione (1) to yield the corresponding xanthendione derivative (23). On the other hand, with o-methoxycinnamaldehyde an impure product formed and the p-methoxy isomer afforded the corresponding 2-arylpyran (25). The NMR spectral data of the compounds are briefly discussed.

  DOI：

  10.1080/10426500490494741

文献信息

• Envirocat EPZ-10: A Solid Acid Catalyst for the Synthesis of 1,8-Dioxo-octahydroxanthenes in Aqueous Medium
  作者：D. M. Pore、T. S. Shaikh、N. G. Patil、S. B. Dongare、U. V. Desai

  DOI：10.1080/00397910903221027

  日期：2010.7.12

  An efficient method for synthesis of 1,8-dioxo-octahydroxanthenes using EPZ-10 as a heterogeneous catalyst is developed. In this method, aldehydes and dimedone / cyclohexane-1,3-dione are heated at 70 °C in the presence of a catalytic amount of EPZ-10 in water as a universal solvent, affording the corresponding 1,8-dioxo-octahydroxanthenes in moderate to excellent yields. Also, domino Knoevenagel /

  开发了一种使用 EPZ-10 作为非均相催化剂合成 1,8-二氧代-八氢氧杂蒽的有效方法。在该方法中，醛和二甲酮/环己烷-1,3-二酮在作为通用溶剂的水中催化量的 EPZ-10 存在下在 70 °C 下加热，得到相应的 1,8-二氧代-八氢氧杂蒽中等至极好的产量。此外，在没有任何催化剂的情况下，多米诺骨牌 Knoevenagel / 杂迈克尔加成反应被描述为具有优异的产率。该方法的主要优点是收率高、反应时间短、操作简便。这种绿色方案适用于二甲酮和环己烷-1,3-二酮。
• Glycerol as a promoting medium for electrophilic activation of aldehydes: catalyst-free synthesis of di(indolyl)methanes, xanthene-1,8(2H)-diones and 1-oxo-hexahydroxanthenes
  作者：Fei He、Peng Li、Yanlong Gu、Guangxing Li

  DOI：10.1039/b916015a

  日期：——

  Glycerol was used, for the first time, as a green and effective promoting medium for electrophilic activation of aldehydes, and with which, a catalyst-free system for some reactions that conventionally carried out using acid catalysts, such as synthesis of di(indolyl)methanes, 3,4,5,6,7,9-hexahydro-9-aryl-1H-xanthene-1,8(2H)-dione and 1-oxo-hexahydroxanthenes, was developed.

  甘油首次被用作绿色有效的促进介质，用于醛的电亲和活化，并基于此开发了一种无催化剂的体系，用于一些传统上使用酸催化剂进行的反应，例如二(吲哚基)甲烷、3,4,5,6,7,9-六氢-9-芳基-1H-黄酮-1,8(2H)-二酮和1-氧基-六氢黄酮的合成。
• Efficient synthesis of 1,8-dioxo-octahydroxanthenes catalyzed by β-cyclodextrin grafted with butyl sulfonic acid in aqueous media
  作者：Kai Gong、Hualan Wang、Shuxin Wang、Ying Wang、Jinghua Chen

  DOI：10.1016/s1872-2067(15)60888-9

  日期：2015.8

  β-Cyclodextrin was functionalized with butyl sulfonic acid to give an efficient, eco-friendly catalyst for the synthesis of 1,8-dioxo-octahydroxanthenes via the one-pot condensation of aromatic aldehydes and active methylene carbonyl compounds in aqueous media. This new methodology offers several advantages such as excellent yields, short reaction time, a simple procedure and mild reaction conditions

  β-环糊精用丁基磺酸官能化，通过芳香醛和活性亚甲基羰基化合物在水性介质中的一锅缩合反应，为合成 1,8-二氧代-八氢氧杂蒽提供了一种高效、环保的催化剂。这种新方法具有多种优势，例如收率高、反应时间短、程序简单和反应条件温和。此外，催化剂可以很容易地回收和重复使用多达五次，而不会显着降低其活性。
• Facile and efficient synthesis of xanthenedione derivatives promoted by niobium pentachloride
  作者：Willian H. dos Santos、Luiz C. Da Silva-Filho

  DOI：10.1515/chempap-2016-0098

  日期：2016.1.1

  Xanthenedione derivatives were synthesised in one-pot reactions between arylaldehyde derivatives and 1,3-cyclohexanedione promoted by niobium pentachloride. This new method is simple, costeffective, high-yielding with a good variety of substrates generality, and can be conducted within reasonable reaction times.

  五氧化二铌衍生物是通过芳基醛衍生物与五氯化铌促进的1,3-环己二酮之间的一锅反应合成的。这种新方法简单，经济高效，产率高，具有多种底物通用性，并且可以在合理的反应时间内进行。
• Alumina-sulfuric acid catalyzed eco-friendly synthesis of xanthenediones
  作者：Amit Pramanik、Sanjay Bhar

  DOI：10.1016/j.catcom.2011.12.036

  日期：2012.4

  Alumina-sulfuric acid has been developed as a cost-effective, recyclable, heterogeneous solid acid catalyst for the eco-friendly synthesis of 9-aryl-1,8-dioxododecahydroxanthenes and 9-aryl-3,3,6,6-tetramethyl-1,8-dioxooctahydroxanthenes through the condensation of cyclic 1,3-diketones with different aryl and heteroaryl aldehydes. (C) 2012 Elsevier BM. All rights reserved.