3,3,6,6-tetramethyl-9-(2-bromophenyl)-3,4,5,6,9,10-hexahydroacridine-1,8(2H,7H)-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: 3,3,6,6-tetramethyl-9-(2-bromophenyl)-3,4,5,6,9,10-hexahydroacridine-1,8(2H,7H)-dione
• 英文别名: 9-(2-bromophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H, 5H)-dione；9-(2-bromophenyl)-3,4,6,7,9,10-hexahydro-3,3,6,6-tetramethyl-1,8(2H,5H)-acridinedione；9-(2-bromophenyl)-3,3,6,6-tetramethyl-2,4,5,7,9,10-hexahydroacridine-1,8-dione
• 化学式: C₂₃H₂₆BrNO₂
• 分子量: 428.369
• InChiKey: DROXDQBZPKHOBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 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：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 在 ammonium acetate 作用下， 以 水 为溶剂， 反应 7.0h， 生成 3,3,6,6-tetramethyl-9-(2-bromophenyl)-3,4,5,6,9,10-hexahydroacridine-1,8(2H,7H)-dione
  参考文献：
  名称：

  在水性介质中有效合成吖啶二酮

  摘要：

  摘要 使用水作为反应介质，无需色谱纯化，就可以分两步高效合成吖啶二酮。第一步涉及二甲酮与乙酸铵反应以在水中产生烯胺酮，其在与各种醛进一步反应时产生在水性介质中的吖啶二酮。该反应的优点是用水作溶剂，不添加催化剂，产品收率高，纯度好。图形概要

  DOI：

  10.1080/00397911.2017.1304556

文献信息

• Acridine derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US05969139A1

  公开（公告）日：1999-10-19

  The invention relates to new and known tricyclic dione derivatives of the general formula ##STR1## wherein W represents hydrogen or lower alkyl; X represents lower alkyl; Y represents NR1; R.sup.1 represents hydrogen, lower alkyl, lower alkoxycarbonyl or lower alkoxycarbonyl-lower alkyl; Z represents aryl or heteroaryl optionally substituted by one or more halo, cyano, nitro, lower alkyl, halo-lower alkyl, lower alkoxy, halo-lower alkoxy, COR.sup.2, OCOR.sup.2, CO.sub.2 R.sup.2, OR.sup.2, S(O).sub.n R.sup.2, NR.sup.2 R.sup.3, N(R.sup.4)COR.sup.5, Ar, Ar-lower alkyl, Het or Het-lower alkyl substituents and/or on adjacent carbon atoms by lower alkylenedioxy; R.sup.2, R.sup.3, R.sup.4 and R.sup.5 each individually represent hydrogen, lower alkyl, Ar, Ar-lower alkyl, Het or Het-lower alkyl substituents; or R.sup.2 and R.sup.3 together represent the group --CH.dbd.CH--CH.dbd.CH-- or --CH.dbd.N--CH.dbd.CH--; Ar represents aryl optionally substituted by one or more halo, lower alkyl, lower alkoxy or nitro substituents; Het represents heteroaryl optionally substituted by one or more halo, lower alkyl, lower alkoxy or nitro substituents; and n stands for 0, 1 or 2 and to their salts which are inhibitors of herpes simplex virus thymidine kinase.

  该发明涉及一般式##STR1##的新型和已知的三环二酮衍生物，其中W代表氢或较低的烷基；X代表较低的烷基；Y代表NR1；R.sup.1代表氢、较低的烷基、较低的烷氧羰基或较低的烷氧羰基-较低的烷基；Z代表芳基或杂芳基，可选择地被一个或多个卤素、氰基、硝基、较低的烷基、卤代较低的烷基、较低的烷氧基、卤代较低的烷氧基、COR.sup.2、OCOR.sup.2、CO.sub.2R.sup.2、OR.sup.2、S(O).sub.nR.sup.2、NR.sup.2R.sup.3、N(R.sup.4)COR.sup.5、Ar、Ar-较低的烷基、Het或Het-较低的烷基取代，和/或在相邻碳原子上被较低的烷基二氧代取代；R.sup.2、R.sup.3、R.sup.4和R.sup.5分别独立地代表氢、较低的烷基、Ar、Ar-较低的烷基、Het或Het-较低的烷基取代；或R.sup.2和R.sup.3一起代表--CH.dbd.CH--CH.dbd.CH--或--CH.dbd.N--CH.dbd.CH--的基团；Ar代表芳基，可选择地被一个或多个卤素、较低的烷基、较低的烷氧基或硝基取代；Het代表杂芳基，可选择地被一个或多个卤素、较低的烷基、较低的烷氧基或硝基取代；n代表0、1或2，以及其抑制单纯疱疹病毒胸苷激酶的盐。
• Green and efficient synthesis of acridine-1,8-diones and hexahydroquinolines via a KH2PO4 catalyzed Hantzsch-type reaction in aqueous ethanol
  作者：Shi-Jun Yü、Si Wu、Xin-Min Zhao、Cheng-Wei Lü

  DOI：10.1007/s11164-016-2814-2

  日期：2017.5

  A simple, clean, and economical methodology for the synthesis of acridine-1,8-dione and hexahydroquinoline derivatives via Hantzsch-type condensation has been described. This study highlights the development of a new green pathway for the preparation of substituted 1,4-dihydropyridines derivatives. The mild, cheap, and nontoxic potassium dihydrogen phosphate (KH2PO4) is proved to be an efficient catalyst for the above multi-component reaction to get excellent yields. Widely available and mostly benign catalyst, eco-friendly solvent, and easy purification are among the several attractive features.

  本文描述了一种通过Hantzsch型缩合反应合成吖啶-1,8-二酮和六氢喹啉衍生物的简单、清洁且经济的方法。该研究突出了为制备取代的1,4-二氢吡啶衍生物开发的新型绿色合成途径。温和、廉价且无毒的磷酸二氢钾（KH2PO4）被证明是上述多组分反应的有效催化剂，能够获得优异的产率。广泛可用且基本上无害的催化剂、环保溶剂以及容易的纯化过程是该方法的几个吸引人的特点。
• CoFe ₂ O ₄ @SiO ₂ ‐NH ₂ ‐Co ^II NPs catalyzed Hantzsch reaction as an efficient, reusable catalyst for the facile, green, one‐pot synthesis of novel functionalized 1,4‐dihydropyridine derivatives
  作者：Ali Allahresani、Mehri Mohammadpour Sangani、Mohammad Ali Nasseri

  DOI：10.1002/aoc.5759

  日期：2020.9

  A magnetically heterogeneous CoFe2O4@SiO2‐NH2‐CoII nanoparticle was synthesized by the immobilization of Co (II) complex onto CoFe2O4@SiO2 nanoparticles, and the heterogeneous magnetic nanocatalyst was characterized by XRD, TEM, TGA, EDX, and FT‐IR techniques. Then, the green and reusable method was introduced for a multicomponent synthesis of 1,4‐dihydropyridine derivatives via Hantszch reaction.

  通过将Co（II）络合物固定在CoFe 2 O 4 @SiO 2上，合成了磁性异质的CoFe 2 O 4 @SiO 2 -NH 2 -Co II纳米颗粒。通过XRD，TEM，TGA，EDX和FT-IR技术对多相磁性纳米催化剂进行了表征。然后，引入了绿色且可重复使用的方法，用于通过Hantszch反应进行多组分合成1,4-二氢吡啶衍生物。在这种磁性纳米催化剂的存在下，在EtOH /水（1：1）中，通过醛，乙酰乙酸乙酯和乙酸铵的反应进行1,4-二氢吡啶衍生物的合成。简单的后处理，短的反应时间，优异的收率（60–96％）以及绿色溶剂是这种新颖方法的优点，并且无需色谱分离即可纯化相应的产物。
• An efficient and green preparation of 9-arylacridine-1,8-dione derivatives
  作者：Xuesen Fan、Yanzhen Li、Xinying Zhang、Guirong Qu、Jianji Wang

  DOI：10.1002/hc.20410

  日期：2007.11

  9-Arylacridine-1,8-dione derivatives were prepared in an ionic liquid medium in the presence of CeCl3 ċ 7H2O through an one-pot procedure. The method presented here has the advantages of environmental benignancy, good-to-excellent yields, and simple operational procedure. Moreover, the solvent and catalyst can be easily recovered and reused for several runs without obvious loss of activity. © 2007

  9-Arylacridine-1,8-dione 衍生物是在离子液体介质中在 CeCl3 ċ 7H2O 存在下通过一锅法制备的。这里介绍的方法具有环境友好、良率高、操作简单等优点。此外，溶剂和催化剂可以很容易地回收并重复使用多次运行而不会明显损失活性。© 2007 Wiley Periodicals, Inc. 杂原子化学 18:786–790, 2007; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20410
• Xanthene and acridine derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US06162918A1

  公开（公告）日：2000-12-19

  The invention relates to new and known tricyclic dione derivatives of the general formula ##STR1## and to their salts which are inhibitors of herpes simplex virus thymidine kinase in the treatment and prophylaxis of infections caused by herpes simplex virus.

  本发明涉及一种新的和已知的三环酮衍生物，其一般式为##STR1##以及它们的盐，它们是单纯疱疹病毒胸腺嘧啶激酶的抑制剂，在单纯疱疹病毒感染的治疗和预防中使用。