3,3-dimethyl-9-(4-methoxyphenyl)-1,2,3,4,9,10-hexahydrobenzo[a]acridine-1-one | 128225-08-1

• 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: 3,3-dimethyl-9-(4-methoxyphenyl)-1,2,3,4,9,10-hexahydrobenzo[a]acridine-1-one
• 英文别名: 12-(4-methoxyphenyl)-9,9-dimethyl-8,9,10,12-tetrahydrobenzo[a]acridin-11(7H)-one；12-(4-methoxyphenyl)-9,9-dimethyl-7,8,10,12-tetrahydrobenzo[a]acridin-11-one
• CAS: 128225-08-1
• 化学式: C₂₆H₂₅NO₂
• 分子量: 383.49
• InChiKey: DPKWKMOIEYMTCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,3-dimethyl-9-(4-methoxyphenyl)-1,2,3,4,9,10-hexahydrobenzo[a]acridine-1-one 在 chromium(VI) oxide 作用下， 以 溶剂黄146 为溶剂， 以75%的产率得到12-(4-Methoxy-phenyl)-9,9-dimethyl-9,10-dihydro-8H-benzo[a]acridin-11-one
  参考文献：
  名称：

  Martinez, Roberto; Cortes, Eduardo; Toscano, R. Alfredo, Journal of Heterocyclic Chemistry, 1990, vol. 27, # 2, p. 363 - 366

  摘要：

  DOI：
• 作为产物：
  描述：

  N-[(4-methoxyphenyl)methylene]-2-naphthalenamine 、 5,5-二甲基-1,3-环己二酮 在 苄基三乙基氯化铵 作用下， 以 水 为溶剂， 反应 5.0h， 以97%的产率得到3,3-dimethyl-9-(4-methoxyphenyl)-1,2,3,4,9,10-hexahydrobenzo[a]acridine-1-one
  参考文献：
  名称：

  一种简单清洁的合成聚氢ac啶和喹啉衍生物的程序：席夫碱与1,3-二羰基化合物在水性介质中的反应

  摘要：

  通过席夫碱与1的反应，可以很好地收率很好地完成苯并[ c ] ac啶，苯并[ a ] ac啶，吡啶并[2,3- c ] ac啶和苯并[ f ]喹啉衍生物的清洁，简单合成。TEBA催化的水性介质中的3-二羰基化合物。通过1 H NMR，IR和元素分析对结构进行表征，并通过X射线衍射研究证实。

  DOI：

  10.1016/j.tetlet.2005.08.091

文献信息

• A clean synthesis of polyhydroacridine and indenoquinoline derivatives catalyzed by triethylbenzylammonium chloride in aqueous media
  作者：Xiang-Shan Wang、Mei-Mei Zhang、Zhao-Sen Zeng、Da-Qing Shi、Shu-Jiang Tu、Xian-Yong Wei、Zhi-Min Zong

  DOI：10.1002/jhet.5570430426

  日期：2006.7

  An efficient and convenient synthesis of benzo[a]acridines and indeno[1,2-b]benzo[f]quinolines was achieved in high yields by the reaction of N-arylidenenaphthalen-2-amine with 1,3-dicarbonyl compounds catalyzed with triethylbenzylammmonium chloride (TEBAC) in aqueous media. The structures were established by spectroscopic data and further confirmed by X-ray analysis. This method provides several advantages

  通过N-芳烯萘-2-胺与1,3-二羰基化合物的反应，可以高效合成苯并[ a ] r啶和茚并[1,2- b ]苯并[ f ]喹啉。三乙基苄基氯化铵（TEBAC）在水性介质中。通过光谱数据确定结构，并通过X射线分析进一步确认。该方法具有许多优点，例如中性条件，高收率和简单的后处理程序。另外，选择水作为绿色和可循环使用的溶剂。
• N,N-disulfo-1,1,3,3-tetramethylguanidinium carboxylate ionic liquids as reusable homogeneous catalysts for multicomponent synthesis of tetrahydrobenzo[ a ]xanthene and tetrahydrobenzo[ a ]acridine derivatives
  作者：Arup Kumar Dutta、Pinky Gogoi、Susmita Saikia、Ruli Borah

  DOI：10.1016/j.molliq.2016.11.112

  日期：2017.1

  carboxylate ionic liquids [DSTMG][CX3COO], ( where X = H, Cl, F) were prepared as viscous liquids from the reaction of [DSTMG][Cl] with equimolar amount of three carboxylic acids (AcOH, CCl3COOH and CF3COOH) for the first time at 60 °C in 1 h. Their structures were confirmed from IR, NMR and elemental analyses data. The Hammett acidity and TGA analysis were also investigated. The two ionic liquids

  从[DSTMG] [Cl]的反应中制备了三种新的–SO 3 H官能化的N，N-二硫代-四甲基胍盐羧酸盐离子液体[DSTMG] [CX 3 COO]（其中X = H，Cl，F）。在60°C下于1小时内首次用等摩尔量的三种羧酸（AcOH，CCl 3 COOH和CF 3 COOH）。由IR，NMR和元素分析数据证实了它们的结构。还研究了哈米特酸度和TGA分析。两个离子液体[DSTMG] [CF 3 COO]和[DSTMG] [四氯化碳3 COO]被作为用于一锅合成四氢可重复使用的均相催化剂[一个]呫吨酮和四氢苯并[一无溶剂热法制备] ac啶酮。首次观察到在IL催化剂存在下，使用2-萘酚作为反应物通过四组分途径制备了四氢苯并[ a ] ac啶酮。
• An efficient one-pot synthesis of polyhydrobenzoacridine-1-one derivatives under microwave irradiation without catalyst
  作者：Shujiang Tu、Runhong Jia、Bo Jiang、Yan Zhang、Junyong Zhang

  DOI：10.1002/jhet.5570430629

  日期：2006.11

  A series of 3,3-dimethyl-9-substituted-1,2,3,4,9,10-hexahydrobenzo[c] acridine-1-ones and 3,3-dimethyl-9-substituted-1,2,3,4,9,10-hexahydrobenzo[a] acridine-1-ones were synthesized by the reaction of an aldehyde, α-naphthylamine or β-naphthylamine and dimedone under microwave irradiation with short times and high yields.

  一系列3,3-二甲基-9-取代的1,2,3,4,9,10-六氢苯并[ c ] a啶-1-酮和3,3-二甲基-9-取代的1,2,3通过醛，α-萘胺或β-萘胺与二甲酮在微波辐射下短时间，高收率反应合成了4,9,10-六氢苯并[ a ] a啶-1-酮。
• The first example of glucose-containing Brønsted acid synthesis and catalysis: efficient synthesis of tetrahydrobenzo[α]xanthens and tetrahydrobenzo[α]acridines in water
  作者：Yu Wan、Xiao-xiao Zhang、Chao Wang、Ling-ling Zhao、Liang-feng Chen、Gui-xiang Liu、Shu-ying Huang、Shu-ning Yue、Wen-li Zhang、Hui Wu

  DOI：10.1016/j.tet.2013.03.029

  日期：2013.5

  Glucose sulfonic acid (GSA) was synthesized for the first time and used as an efficient catalyst for the preparation of tetrahydrobenzo[alpha]xanthens and tetrahydrobenzo[alpha]acridines via the reaction of aromatic aldehydes, 2-naphthol (or beta-naphthylamine), and dimedone in water. Up to four new bonds and one new ring were formed in one-pot with water as the only by-product in these two reactions. The work opens up a new and efficient synthesis and application of sugar-containing Bronsted acid. (C) 2013 Elsevier Ltd. All rights reserved.