9-(3,4-dichlorophenyl)-3,3,6,6-tetramethyl-10-(4-tolyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 9-(3,4-dichlorophenyl)-3,3,6,6-tetramethyl-10-(4-tolyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione
• 英文别名: 9-(3,4-dichlorophenyl)-10-(4-methylphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione；3,3,6,6-tetramethyl-1,8-dioxo-9-(3,4-dichlorophenyl)-10-(4-methylphenyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridine；9-(3,4-dichlorophenyl)-3,3,6,6-tetramethyl-10-(4-methylphenyl)-4,5,7,9-tetrahydro-2H-acridine-1,8-dione
• 化学式: C₃₀H₃₁Cl₂NO₂
• 分子量: 508.488
• InChiKey: DPCIYAVWTYCDAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  [1-(3,4-Dichloro-phenyl)-meth-(E)-ylidene]-p-tolyl-amine 、 5,5-二甲基-1,3-环己二酮 以 乙二醇 为溶剂， 反应 0.08h， 以92%的产率得到9-(3,4-dichlorophenyl)-3,3,6,6-tetramethyl-10-(4-tolyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione
  参考文献：
  名称：

  席夫碱与二甲酮的新反应：微波辐射下cr啶衍生物的新方法

  摘要：

  描述了席夫碱的新型级联反应。反应中提供的产物取决于两种原料的比例。提出了反应的可能机理，该机理经历了碳原子和氮原子之间的键的断裂和新形成。

  DOI：

  10.1002/jhet.5570440114

文献信息

• Green and expeditious synthesis of 1,8-dioxodecahydroacridine derivatives catalysed by protic pyridinium ionic liquid
  作者：HESHMATOLLAH ALINEZHAD、MAHMOOD TAJBAKHSH、MOHAMMAD NOROUZI、SAEED BAGHERY、JAMSHID RAKHTSHAH

  DOI：10.1007/s12039-013-0517-4

  日期：2013.11

  The Hantzsch three-component condensation reaction of various aromatic aldehydes, 1,3-dione and aniline derivatives in the presence of 2-methylpyridinium trifluoromethanesulphonate ([2-MPyH]OTf) as green and highly efficient catalysts in water affords 1,8-dioxodecahydroacridine derivatives in good to excellent yields. This reaction has been carried out in the presence of 1 mol% of [2-MPyH]OTf at room

  在3-甲基吡啶三氟甲烷磺酸酯（[2-MPyH] OTf）存在下，各种芳香族醛，1,3-二酮和苯胺衍生物的汉茨三组分缩合反应作为绿色高效的水溶液，可提供1,8-二氧杂双氢hydro啶衍生品，收益率极高。该反应在室温下在1mol％的[2-MPyH] OTf存在下进行。与传统的合成方法相比，所描述的新颖的合成方法具有条件温和，反应时间短，产率高，简单且易于后处理的多个优点。 使用[2-MPyH] OTf作为离子液体催化剂，以良好至极佳的收率合成了1,8-二氧十二烷基氢化hydro啶衍生物。
• An Improved and Benign Synthesis of 9,10-Diarylacridine-1,8-dione and Indenoquinoline Derivatives from 3-Anilino-5,5-dimethylcyclohex-2-enones, Benzaldehydes, and 1,3-Dicarbonyl Compounds in an Ionic Liquid Medium
  作者：Xiang-Shan Wang、Mei-Mei Zhang、Hong Jiang、Da-Qing Shi、Shu-Jiang Tu、Xian-Yong Wei、Zhi-Min Zong

  DOI：10.1055/s-2006-950365

  日期：——

  excellent yields. Furthermore, the interesting unsymmetrical 9,10-diarylacridine-1,8-dione moiety with different groups in the 3- and 6-positions and indenoquinoline derivatives were obtained and are reported here for the first time in the literature. The Knoevenagel condensation and Michael addition intermediates were obtained successfully. A possible mechanism of the reaction is discussed in detail.

  9,10-二芳基吖啶-1,8-二酮和茚并喹啉衍生物的改进和绿色合成是通过3-苯胺基-5,5-二甲基环己-2-烯酮、苯甲醛和1,3-二羰基化合物的反应完成的。离子液体介质[bmim + ][BF 4 - ]。不仅含有给电子基团的取代苯胺，而且含有吸电子基团的苯胺均具有优异的产率。此外，获得了有趣的不对称 9,10-diarylacridine-1,8-dione 部分，在 3 位和 6 位具有不同的基团和茚并喹啉衍生物，并在文献中首次报道。成功获得了Knoevenagel缩合和迈克尔加成中间体。详细讨论了该反应的可能机理。
• New reaction of schiff base with dimedone: New method for the acridine derivatives under microwave irradiation
  作者：Shujiang Tu、Tuanjie Li、Yan Zhang、Feng Shi、Jianing Xu、Qian Wang、Jinpeng Zhang、Xiaotong Zhu、Bo Jiang、Runhong Jia、Junyong Zhang

  DOI：10.1002/jhet.5570440114

  日期：2007.1

  A novel cascade reaction of Schiff's base was described. The products afforded in the reaction depended on the ratio of the two starting materials. A possible mechanism of the reactions is proposed, which underwent the breaking and new formation of the bond between carbon atom and nitrogen atom.

  描述了席夫碱的新型级联反应。反应中提供的产物取决于两种原料的比例。提出了反应的可能机理，该机理经历了碳原子和氮原子之间的键的断裂和新形成。
• Brønsted acidic imidazolium salts containing perfluoroalkyl tails catalyzed one-pot synthesis of 1,8-dioxo-decahydroacridines in water
  作者：Wei Shen、Li-Min Wang、He Tian、Jun Tang、Jian-jun Yu

  DOI：10.1016/j.jfluchem.2009.02.014

  日期：2009.6

  One-pot three-component synthesis of 1,8-dioxo-9,10-diaryl-decahydroacridines in water was efficiently realized in the presence of the Bronsted acidic imidazolium salts containing perfluoroalkyl tails in good yields. The method provided several advantages such as low catalyst loading; recycle of the catalyst and simple work procedure. (c) 2009 Elsevier B.V. All rights reserved.
• Efficient, Solvent-Free, Microwave-Enhanced Condensation of 5,5-Dimethyl-1,3-cyclohexanedione with Aldehydes and Imines Using LiBr as Inexpensive, Mild Catalyst
  作者：Dhruva Kumar、Jagir S. Sandhu

  DOI：10.1080/00397910902987792

  日期：2010.2.2

  Efficient, solvent-free, microwave-enhanced condensation of 5,5-dimethyl-1,3-cyclohexanedione with aldehydes using LiBr as catalyst affords xanthenediones. Imines gave only bis-5,5-dimethyl-1,3-cyclohexanediones at high power; a slightly longer period gave xanthenediones. In both types of reactions, the products are obtained in very good to excellent yields. The present protocol is inexpensive and ecofriendly.