3,3,6,6-tetramethyl-9-(4-N,N’-dimethylaminophenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione | 40588-52-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3,3,6,6-tetramethyl-9-(4-N,N’-dimethylaminophenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
• 英文别名: 3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-9-(4-(dimethylamino)phenyl)-2H-xanthene-1,8(5H,9H)-dione；9-(4-(dimethylamino)phenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione；2,2,5,5-tetramethyl-9-(4'-dimethylaminophenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione；9-(4-N,N-dimethylphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione；3,3,6,6-tetramethyl-9-(4-dimethylaminophenyl)-1,8-dioxo-octahydroxanthene；3,3,6,6-tetramethyl-9-(4-N,N-dimethylphenyl)-1,8-dioxooctahydroxanthene；9-[4-(dimethylamino)phenyl]-3,3,6,6-tetramethyl-4,5,7,9-tetrahydro-2H-xanthene-1,8-dione
• CAS: 40588-52-1
• 化学式: C₂₅H₃₁NO₃
• 分子量: 393.526
• InChiKey: IEEHXXVKVCFQMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 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：

  4-Dimethylamino-α.α-bis-(2.6-dioxo-4.4-dimethyl-phenyl)-toluol 在 盐酸 、 乙醇 作用下， 生成 3,3,6,6-tetramethyl-9-(4-N,N’-dimethylaminophenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
  参考文献：
  名称：

  醛的甲酮衍生物。

  摘要：

  DOI：

  10.1021/jo01171a014

文献信息

• Simple and cost effective acid catalysts for efficient synthesis of 9-aryl-1,8-dioxooctahydroxanthene
  作者：A. Ilangovan、S. Muralidharan、P. Sakthivel、S. Malayappasamy、S. Karuppusamy、M.P. Kaushik

  DOI：10.1016/j.tetlet.2012.11.058

  日期：2013.2

  DMSO or aq HBr (10 mol %) is developed as an efficient and cost effective acid catalyst for the simple one-pot synthesis of 9-aryl-1,8-dioxooctahydroxanthene derivatives. Reaction of aromatic aldehyde (1 equiv) and dimedone (2 equiv) in the presence of CaCl2 (20 mol %) in CHCl3 at room temperature gave the open chain analogue of 1,8-dioxooctahydroxanthene. Similarly, aq HBr (10 mol %) in water at reflux

  开发了在DMSO或HBr水溶液（10 mol％）中的CaCl 2（20 mol％）分散体，作为一种简单，一锅合成9-芳基-1,8-二氧代八氢氧杂蒽衍生物的有效且具有成本效益的酸催化剂。在室温下，在CHCl 3中，在CaCl 2（20 mol％）存在下，芳族醛（1当量）和二甲酮（2当量）进行反应，得到1,8-二氧代八氢氧杂蒽的开链类似物。类似地，在回流温度下在水中的HBr水溶液（10mol％）产生高产率的9-芳基-1，8-二氧代八氢氧杂蒽衍生物。使用廉价，环保且易于获得的催化剂，易于后处理和产物分离，使这些程序成为合成任何一种产物的方便方法。
• Graphene Oxide Incorporated Strontium Nanoparticles as a Highly Efficient and Green Acid Catalyst for One-Pot Synthesis of Tetramethyl-9-aryl-hexahydroxanthenes and 13-Aryl-5H-dibenzo[b,i]xanthene-5,7,12,14(13H)-tetraones Under Solvent-Free Conditions
  作者：Seyyed Rasul Mousavi、Hamid Rashidi Nodeh、Elham Zamiri Afshari、Alireza Foroumadi

  DOI：10.1007/s10562-019-02675-0

  日期：2019.4.15

  applying graphene oxide/strontium as a nanocatalyst for xanthene derivatives synthesis. The key potential benefits of the present method are including high yields, short reaction time, easy workup, recyclability of catalyst and ability to tolerate a variety of functional groups which gives economical as well as ecological rewards. The nanocatalyst easily separated from the reaction mixture easily by

  合成了一种高效、廉价且可回收的氧化石墨烯/锶纳米催化剂，并将其应用于芳香醛和二甲酮/洛森的伪三组分一锅环缩合反应中，得到相应的 3,3,6,6-四甲基-9-芳基-3,4,5,6,7,9-六氢-1H-呫吨-1,8(2H)-二酮和13-芳基-5H-二苯并[b,i]呫吨-5,7,12,14( 13H)-四酮在无溶剂条件下高产率。据我们所知，目前还没有关于将氧化石墨烯/锶用作合成呫吨衍生物的纳米催化剂的文献报道。本方法的主要潜在优势包括高产率、反应时间短、易于后处理、催化剂的可回收性以及耐受各种官能团的能力，从而带来经济和生态回报。
• Bi-SO3H functionalized ionic liquid based on DABCO as a mild and efficient catalyst for the synthesis of 1,8-dioxo-octahydro-xanthene and 5-arylmethylene-pyrimidine-2,4,6-trione derivatives
  作者：Farhad Shirini、Mohaddeseh Safarpoor Nikoo Langarudi、Mohadeseh Seddighi、Omid Goli Jolodar

  DOI：10.1007/s11164-014-1905-1

  日期：2015.11

  1,8-Dioxo-octahydro-xanthenes are easily prepared via the condensation of aldehydes with 1,3-cyclohexadione and/or dimedone using N-sulfonated DABCO as a new and efficient catalyst. This reagent is also efficiently able to catalyze the condensation of aldehydes with barbituric acid leading to 5-arylmethylene-pyrimidine-2,4,6-triones. The structure of the products was characterized by their IR, 1H NMR, and 13C NMR spectroscopy. The present methodology offers several advantages such as ease of preparation and handling of the catalyst, high yields, simple and green procedure, low cost, short reaction times, easy work-up, and preformation of the reaction in the absence of solvent or in water as a green solvent.

  1,8-二氧杂-八氢化咕吨类化合物可通过醛与1,3-环己二酮和/或双甲酮在新型高效的N-磺化DABCO催化剂作用下缩合反应制得。该试剂同样能高效催化醛与巴比妥酸的缩合反应，生成5-芳亚甲基-嘧啶-2,4,6-三酮。产物结构通过其红外光谱、核磁共振氢谱和碳谱得以表征。本方法具有多种优势，如催化剂制备与处理简便、产率高、操作简单且环保、成本低、反应时间短、后处理简便，以及可在无溶剂条件下或使用水作为绿色溶剂的情况下预先进行反应。
• Synthesis and Characterization of a Novel Ionic Liquid Based on N,N,N,N-tetramethylethylenediamine and its Application in the Synthesis of 1,8-dioxo-octahydro Xanthenes
  作者：Zahra Abdi Piralghar、Mohammad Mahmoodi Hashemi、Ali Ezabadi

  DOI：10.2174/1386207321666180828092546

  日期：2018.11.15

  and characterized a novel Brönsted acidic ionic liquid from the reaction of N, N, N', N'-tetramethylethylenediamine with chlorosulfonic acid and explored its catalytic activity in 1, 8-dioxo-octahydroxanthenes synthesis. MATERIALS AND METHODS Dimedone, aryl aldehydes, and the ionic liquid as the catalyst were reacted under solvent-free conditions. The progressive of the reaction was monitored by a thin

  目的和目的在这项工作中，我们从N，N，N'，N'-四甲基乙二胺与氯磺酸的反应中合成并表征了一种新型的布朗斯台德酸性离子液体，并探索了其在1，8-二氧-八氢氧杂蒽合成中的催化活性。材料与方法使二甲酮，芳基醛和作为催化剂的离子液体在无溶剂条件下反应。通过薄层色谱法（乙酸乙酯/正己烷＝ 1/5）监测反应的进行。通过与文献报道的比较，将所有产物表征为其光谱数据和熔点的基础。结果制得的离子液体已成功用于1的合成 在无溶剂条件下，芳基醛与二甲酮在120°C的反应中，高至高收率的8-二氧杂八氢氧杂蒽。结论这项研究表明该催化剂在无溶剂条件下对1，8-二氧-八氧杂蒽的合成具有令人印象深刻的作用。
• Synthesis of Kaolin/Ag Nanocomposite as an Efficient and Versatile Reagent for the Synthesis of 1,8-Dioxo-Octahydroxanthene Derivatives
  作者：Bahareh Sadeghi、Saeedeh Hashemian

  DOI：10.1080/15533174.2013.776598

  日期：2014.3.16

  Kaolin/Ag nanocomposite was synthesized in a nano reactor by the calcination of the precursor at high temperature, and shown to efficiently catalyze 1,8-dioxo-octahydroxanthene synthesis via condensation of aromatic aldehydes and 5,5-dimethyl-1,3- cyclohexanedione under mild reaction conditions in good to excellent yields.

  高岭土/ Ag纳米复合材料是在高温下通过前驱体的高温煅烧在纳米反应器中合成的，并显示可通过芳族醛与5,5-二甲基-1,3-环己烷二酮的缩合有效催化1,8-二氧-八氢氧杂蒽的合成在温和的反应条件下，收率良好。