3,3,6,6-tetramethyl-9-(2-methylphenyl)-3,4,6,7-tetrahydroacridine-1,8(2H,5H,9H,10H)-dione | 363569-99-7

• 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-methylphenyl)-3,4,6,7-tetrahydroacridine-1,8(2H,5H,9H,10H)-dione
• 英文别名: 9-(2-methylphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro-2H,5H-acridine-1,8-dione；9-(2-methylphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8-dione；Cambridge id 6215741；3,3,6,6-tetramethyl-9-(2-methylphenyl)-2,4,5,7,9,10-hexahydroacridine-1,8-dione
• CAS: 363569-99-7
• 化学式: C₂₄H₂₉NO₂
• 分子量: 363.5
• InChiKey: ZNHUAJKHEFCZCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 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 8.0h， 生成 3,3,6,6-tetramethyl-9-(2-methylphenyl)-3,4,6,7-tetrahydroacridine-1,8(2H,5H,9H,10H)-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

• 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。
• <i>N</i>-Propyl benzoguanamine sulfonic acid supported on magnetic Fe₃O₄ nanoparticles: a novel and efficient magnetically heterogeneous catalyst for the synthesis of 1,8-dioxo-decahydroacridine derivatives
  作者：Masoumeh Gholami Dehbalaei、Naser Foroughifar、Hoda Pasdar、Alireza Khajeh-Amiri

  DOI：10.1039/c7nj03508j

  日期：——

  N-propyl-benzoguanamine-SO3H-stabilized magnetic nanoparticles were prepared as a new heterogeneous acid catalyst in accordance with the principles of green chemistry. The new catalyst is used for the synthesis of derivatives of 1,8-dioxo-decahydroacridine in one-stage via four-partial condensation reactions between aromatic aldehydes, dimedone and ammonium acetate or aniline with high yield and short reaction

  在这项研究中，根据绿色化学原理，制备了N-丙基-苯并胍胺-SO 3 H稳定的磁性纳米颗粒，作为一种新的非均相酸催化剂。新的催化剂用于在单级1,8-二氧代decahydroacridine的衍生物的合成通过芳香醛，和双甲酮乙酸铵或苯胺以高产率和短的反应时间之间的四部分冷凝反应。通过获得的纳米颗粒的结构傅里叶变换红外光谱（IR），场发射扫描电子显微镜（FE-SEM），透射电子显微镜（TEM），能量色散X射线分析（EDXA），X射线衍射（XRD），热重分析（TGA） ，振动样品磁力法（VSM），原子吸收光谱法（AAS）和电感耦合等离子体质谱法（ICP-MS）进行了评估。结果表明，合成的磁性纳米粒子的尺寸为约25nm。非均相催化剂可以容易地通过外部磁体回收，并且可以重复使用几次而不会显着降低催化活性。
• An Efficient One-Pot Four-Component Synthesis of 9-Aryl-Hexahydroacridine-1,8-Dione Derivatives in the Presence of a Molecular Sieves Supported Iron Catalyst
  作者：Ágnes Magyar、Zoltán Hell

  DOI：10.1007/s10562-019-02845-0

  日期：2019.9

  with good to excellent yields (50–99%) via a one-pot four-component reaction of dimedone, aromatic aldehydes and ammonium acetate in the presence of 4 Å molecular sieves modified with iron(III) as an efficient heterogeneous catalyst, in ethanol. The process offers the advantages of high yields, mild reaction conditions and easy work-up procedure. The catalyst can be reused without significant loss of

  在 4 Å 存在下，通过二甲酮、芳香醛和乙酸铵的一锅四组分反应，合成了一系列 9-芳基-六氢吖啶-1,8-二酮，收率从50% 到99%用铁（III）改性的分子筛作为一种有效的多相催化剂，在乙醇中。该工艺具有收率高、反应条件温和、后处理简单等优点。催化剂可以重复使用而不会显着损失活性。图形摘要
• Solvent-free synthesis of polyhydroquinoline and 1,8-dioxodecahydroacridine derivatives through the Hantzsch reaction catalyzed by a natural organic acid: A green method
  作者：Imène Sehout、Raouf Boulcina、Boudjemaa Boumoud、Taous Boumoud、Abdelmadjid Debache

  DOI：10.1080/00397911.2017.1316406

  日期：2017.6.18

  ABSTRACT Solvent-free and high yielding one-pot synthesis of 1,8-dioxodecahydroacridine and polyhydroquinoline derivatives have been described through Hantzsch condensation of various aldehydes, ammonium acetate with cyclic 1,3-dicarbonyl compounds and ethyl acetoacetate in a very simple, efficient, and environmentally benign method using ascorbic acid as a nontoxic organocatalyst. GRAPHICAL ABSTRACT

  摘要 1,8-二氧十氢吖啶和聚氢喹啉衍生物的无溶剂和高产一锅合成已被描述为通过各种醛、乙酸铵与环状 1,3-二羰基化合物和乙酰乙酸乙酯以一种非常简单、高效、以及使用抗坏血酸作为无毒有机催化剂的环境友好方法。图形概要
• Choline Chloride Catalyzed Eco-Friend and Effective One-Pot Synthesis of 9-Arylacridine-1,8-dione and Hexahydroquinoline via Hantzsch Type Reaction
  作者：Chengwei Lv、Shijun Yu、Shengxue Mao、Fei Li、Yue Lv

  DOI：10.3987/com-17-13760

  日期：——

  Choline chloride was utilized to efficiently catalyzed Hantzsch type reaction for the synthesis of 9-arylacridine-1,8-dione and hexahydroquinoline derivatives. The optimized catalytic system benefits from facile operation and separation procedures, in good to excellent yields, and for wide substrate tolerance. This methodology is of interest also due to employing simple and inexpensive choline chloride as catalyst and environmentally benign ethanol as solvent without the use of any harmful organic solvent and toxic metal catalyst.