3,3,6,6-tetramethyl-9-phenyl-3,4,6,7,9,10-hexahydro-2H,5H-acridine-1,8-dione | 2769-21-3

• 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-phenyl-3,4,6,7,9,10-hexahydro-2H,5H-acridine-1,8-dione
• 英文别名: 3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-9-phenylacridine-1,8(2H,5H,9H,10H)-dione；3,3,6,6-tetramethyl-9-phenyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H, 5H)-dione；3,3,6,6-tetramethyl-9-phenyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione；3,3,6,6,-tetramethyl-9-phenyl-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione；9-phenyl-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione；3,3,6,6-tetramethyl-9-phenyl-3,4,6,7-tetrahydroacridine-1,8(2H,5H,9H,10H)-dione；9-phenyl-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8-dione；3,3,6,6-tetramethyl-9-phenyl-1,8-dioxodecahydroacridine；3,3,6,6-tetramethyl-9-phenyl-2,4,5,7,9,10-hexahydroacridine-1,8-dione
• CAS: 2769-21-3
• 化学式: C₂₃H₂₇NO₂
• mdl: MFCD00511127
• 分子量: 349.473
• InChiKey: KFTOHVZIRTYJBU-UHFFFAOYSA-N

物化性质

• 熔点：
  275-277 °C(Solv: methanol (67-56-1))
• 沸点：
  510.9±50.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 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

• 作为反应物：
  描述：

  3,3,6,6-tetramethyl-9-phenyl-3,4,6,7,9,10-hexahydro-2H,5H-acridine-1,8-dione 在 PPA 作用下， 反应 3.0h， 以84%的产率得到3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8-octahydroacridine-1,8-dione
  参考文献：
  名称：

  摘要：

  DOI：

  10.1023/a:1022592302936
• 作为产物：
  描述：

  α-chlorobenzyl isocyanate 在 乙酸铵 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 34.0h， 生成 3,3,6,6-tetramethyl-9-phenyl-3,4,6,7,9,10-hexahydro-2H,5H-acridine-1,8-dione
  参考文献：
  名称：

  Heterocyclization of functionalized heterocumulenes with C,N-and C,O-binucleophiles: VI. Synthesis of carbofused 2,3-dihydro-1,3-oxazin-4-ones and 3,4-dihydro-1,3-oxazin-2-ones

  摘要：

  Condensations of 1-phenyl-2,2,2-trifluoro-1-chloroethyl isocyanate and 1-chlorobenzyl isocyanate with cyclic 1,3-diketones yield respectively carbofused 2,3-dihydro-1,3-oxazin-4-ones and 3,4-dihydro-1,3-oxazin-2-ones.

  DOI：

  10.1134/s1070428007020170

文献信息

• Synthesis of 1,8-Dioxo-decahydroacridine Derivatives <i>via</i> Ru-Catalyzed Acceptorless Dehydrogenative Multicomponent Reaction
  作者：Nandita Biswas、Dipankar Srimani

  DOI：10.1021/acs.joc.1c01075

  日期：2021.7.16

  A Ru-catalyzed acceptorless dehydrogenative multicomponent reaction has been developed. This reaction offers a cost-effective and simple operational strategy to synthesize biologically active 1,8-dioxodecahydroacridine derivatives. The protocol provides a wide range of substrate scope and various functional groups are also well tolerated under the reaction condition. To shed light on the mechanistic

  已经开发了 Ru 催化的无受体脱氢多组分反应。该反应为合成具有生物活性的 1,8-二氧十氢吖啶衍生物提供了一种经济高效且简单的操作策略。该协议提供了广泛的底物范围，并且在反应条件下也可以很好地耐受各种官能团。为了阐明机械和动力学研究，进行了一些对照实验和氘标记实验。还介绍了一个与时间相关的产品分布实验，并进行了反应放大以突出该策略的实际效用。
• Nano-zirconia as an excellent nano support for immobilization of sulfonic acid: a new, efficient and highly recyclable heterogeneous solid acid nanocatalyst for multicomponent reactions
  作者：Ali Amoozadeh、Salman Rahmani、Mehrnoosh Bitaraf、Fatemeh Bolghan Abadi、Elham Tabrizian

  DOI：10.1039/c5nj02430g

  日期：——

  Nano-zirconia-supported sulfonic acid as a novel, highly efficient and recyclable heterogeneous nanocatalyst is reported for the synthesis of multicomponent reactions.

  报告了一种新型的、高效的、可回收的纳米催化剂——纳米氧化锆支撑的磺酸，用于合成多组分反应。

• Merging supramolecular catalysis and aminocatalysis: amino-appended β-cyclodextrins (ACDs) as efficient and recyclable supramolecular catalysts for the synthesis of tetraketones
  作者：Yufeng Ren、Bo Yang、Xiali Liao

  DOI：10.1039/c6ra01002d

  日期：——

  β-CD were synthesized and employed in the catalytic synthesis of a series of tetraketones as supramolecular catalysts in water for the first time. Yields of 58–97% were obtained with up to 30 examples of substrate. The catalyst could be recycled easily, while a 92% yield and 84% rate of catalyst recovery could be achieved after 8 cycles of catalyst recycling. Moreover, a catalytic mechanism merging

  合成了设计良好的，在β-CD的主面上具有不同长度的氨基侧链的氨基附加β-环糊精（ACD），并将其首次用于一系列四酮的催化合成，作为水中的超分子催化剂。使用多达30个底物实例可获得58-97％的产率。该催化剂可以容易地再循环，而在8次催化剂再循环之后，可以达到92％的收率和84％的催化剂回收率。此外，通过详细的1D和2D NMR，ESI-MS和Job图分析，可以提出将超分子催化和氨基催化相结合的催化机理。该协议保留了环境温度，绿色介质，操作简单，基材范围广，产率高，
• USY-zeolite catalyzed synthesis of 1,4-dihydropyridines under microwave irradiation: structure and recycling of the catalyst
  作者：Leonardo H.R. Alponti、Monize Picinini、Ernesto A. Urquieta-Gonzalez、Arlene G. Corrêa

  DOI：10.1016/j.molstruc.2020.129430

  日期：2021.3

  therapeutically and also as visible‐light photoredox catalysts. In this work we report the application of an ultra-stable (US) Y zeolite as a promising green catalyst in the synthesis of a series of 1,4-dihydropyridines under microwave irradiation. Using the optimized reaction conditions, 21 compounds were prepared in 64-96% isolated yields. The recovery and recycle of the USY zeolite are also reported as well

  摘要 Hantzsch 三组分反应是最著名的多组分反应，可提供已用于治疗的二氢吡啶类化合物，也可用作可见光光氧化还原催化剂。在这项工作中，我们报告了超稳定 (US) Y 沸石作为一种有前途的绿色催化剂在微波辐射下合成一系列 1,4-二氢吡啶中的应用。使用优化的反应条件，以 64-96% 的分离产率制备了 21 个化合物。还报告了 USY 沸石的回收和再循环及其完全表征。
• Facile route to synthesize Fe₃O₄@acacia–SO₃H nanocomposite as a heterogeneous magnetic system for catalytic applications
  作者：Reza Taheri-Ledari、Mir Saeed Esmaeili、Zahra Varzi、Reza Eivazzadeh-Keihan、Ali Maleki、Ahmed Esmail Shalan

  DOI：10.1039/d0ra07986c

  日期：——

  Concisely, this catalyst was constructed from acacia gum (gum arabic) as a natural polymeric base, iron oxide magnetic nanoparticles (Fe3O4 NPs), and sulfone functional groups on the surface as the main active catalytic sites. Herein, a convenient preparation method for this nanoscale composite is introduced. Then, essential characterization methods such as various spectroscopic analyses and electron microscopy

  在这项工作中，报道了一种促进 9-苯基六氢吖啶药物衍生物有机多组分合成的新型催化系统。简而言之，该催化剂由阿拉伯树胶（阿拉伯树胶）作为天然聚合物基质、氧化铁磁性纳米粒子（Fe 3 O 4 NPs）和表面上的磺基官能团作为主要活性催化位点构成。本文介绍了这种纳米级复合材料的便捷制备方法。然后，对制备的纳米粉末进行了必要的表征方法，例如各种光谱分析和电子显微镜（EM）。还通过热重分析（TGA）和振动样品磁力测定（VSM）方法精确监测热稳定性和磁性。然后，通过使用参与反应的组分的各种衍生物，在所涉及的有机反应中进一步研究了所提出的催化体系（Fe 3 O 4 @acacia–SO 3 H）的性能。还对这种高效催化剂进行了优化、机理研究和可重复使用性筛选。总体而言，在指定的最佳条件下，各种 9-苯基六氢吖啶衍生物的生成均获得了显着的反应产率 (94%)。