10-benzyl-3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-9-phenylacridine-1,8(2H,5H,9H,10H)-dione | 183737-75-9

• 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: 10-benzyl-3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-9-phenylacridine-1,8(2H,5H,9H,10H)-dione
• 英文别名: 10-benzyl-3,3,6,6-tetramethyl-9-phenyl-3,4,6,7,9,10-hexahydro-2H,5H-acridine-1,8-dione；10-benzyl-3,3,6,6-tetramethyl-9-phenyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione；10-benzyl-9-phenyl-3,3,6,6-tetramethyldecahydroacrydin-1,8-dione；10-benzyl-3,3,6,6-tetramethyl-9-phenyl-4,5,7,9-tetrahydro-2H-acridine-1,8-dione
• CAS: 183737-75-9
• 化学式: C₃₀H₃₃NO₂
• 分子量: 439.598
• InChiKey: ZABZCKZOXNRPKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  33
• 可旋转键数：
  3
• 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

• 作为反应物：
  描述：

  10-benzyl-3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-9-phenylacridine-1,8(2H,5H,9H,10H)-dione 在 镍 、 氢化铝 氢氧化钾 作用下， 以 甲醇 为溶剂， 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：

  十氢ac啶-1,8-二酮的立体定向催化合成全氢ac啶及其同系物

  摘要：

  DOI：

  10.1023/b:cohc.0000037313.98113.1e
• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 在 indium(III) triflate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 10-benzyl-3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-9-phenylacridine-1,8(2H,5H,9H,10H)-dione
  参考文献：
  名称：

  三氟甲磺酸铟 (III) 催化 β-烯胺酮、醛和环状 1,3-二羰基化合物的高效一锅法合成吖啶二酮

  摘要：

  从β-烯胺酮、醛和环状1,3-二酮开始发展催化反应。这些反应的关键策略涉及多米诺诺文格尔缩合/迈克尔加成/环化脱水反应。关键词：吖啶二酮、三氟甲磺酸铟、β-烯胺酮 简介吖啶二酮及其衍生物具有广泛的药学活性，包括抗菌、

  DOI：

  10.5012/bkcs.2012.33.4.1170

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。
• Cross-dehydrogenative regioselective Csp³–Csp²coupling of enamino-ketones followed by rearrangement: an amazing formation route to acridine-1,8-dione derivatives
  作者：Rajib Sarkar、Chhanda Mukhopadhyay

  DOI：10.1039/c5ob02655e

  日期：——

  A new general method for the synthesis of acridine-1,8-diones through CDC coupling of enamino-ketones followed by rearrangement has been developed. This is a Cu(I) catalyzed procedure, based on the cross dehydrogenative coupling of the Csp3–H bond with the Csp2–H bond of enamino-ketones followed by rearrangement to acridine-1,8-diones in the presence of PTSA under an aerobic atmosphere. The synthetic

  已开发出一种新的通用方法，该方法通过烯胺酮的CDC偶联然后重排来合成a啶1,8-二酮。这是Cu（I）催化的程序，基于PTSA存在下Csp 3 -H键与烯氨基酮的Csp 2 -H键的交叉脱氢偶联，然后在PTSA存在下重排为a啶-1,8-二酮在有氧气氛下。合成路线已广泛地适用于广泛的烯氨基酮衍生物的从不同的苄基胺，以及具有脂族伯胺衍生Ç α（SP 3）-H键与各种环状的，无环的1,3-二酮类和也使用死的。
• An efficient route to 1,8-dioxo-octahydroxanthenes and -decahydroacridines using a sulfated zirconia catalyst
  作者：Sandeep S. Kahandal、Anand S. Burange、Sandip R. Kale、Pepijn Prinsen、Rafael Luque、Radha V. Jayaram

  DOI：10.1016/j.catcom.2017.03.017

  日期：2017.7

  Sulfated zirconia results to be a very efficient catalyst for the synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines without tedious work-up procedures. While 1,8-dioxo-octahydroxanthenes are prepared from aldehyde and 5,5-dimethyl-1,3-cyclohexenedione (dimedone), 1,8-dioxo-decahydroacridines are prepared from this reactant mixture with amines. This method provides a mild catalytic

  硫酸化的氧化锆是一种非常有效的催化剂，用于合成1,8-二氧-八氢黄嘌呤和1,8-二氧-十氢ac啶，无需进行繁琐的后处理程序。尽管由醛和5,5-二甲基-1,3-环己二酮（二甲酮）制备1,8-二氧-八氢黄嘌呤，而由该反应物与胺的混合物制备1,8-二氧-十氢ac啶。该方法为合成功能化的x吨和a啶衍生物提供了温和的催化方案。通过XRD，FT-IR，TGA-DSC，SEM-EDAX和表面酸度对催化剂进行了表征，并显示了高达6个连续循环的优异可重复使用性。
• Ceric ammonium nitrate (CAN) catalyzed synthesis of N-substituted decahydroacridine-1,8-diones in PEG
  作者：Mazaahir Kidwai、Divya Bhatnagar

  DOI：10.1016/j.tetlet.2010.03.033

  日期：2010.5

  Polyethylene glycol (PEG) was found to be an inexpensive non-toxic and effective medium for the one-pot synthesis of N-substituted decahydroacridine-1,8-diones in the presence of ceric ammonium nitrate (CAN) as the catalyst in high yields. Also, the solvent system can be recovered and reused; making this protocol economically and potentially viable.

  聚乙二醇（PEG）被发现是用于一锅合成N的廉价的无毒且有效的介质-如以高收率催化剂取代decahydroacridine -1,8-二酮在硝酸铈铵（CAN）的存在下。而且，溶剂系统可以回收和再利用。使该协议在经济上和潜在的可行性。
• Magnetically recoverable, nanoscale-supported heteropoly acid catalyst for green synthesis of biologically active compounds in water
  作者：Ezzat Rafiee、Sara Eavani、Maryam Khodayari

  DOI：10.1016/s1872-2067(12)60645-7

  日期：2013.8

  12-Tungstophosphoric acid supported on aerosil silica and silica-coated gamma-Fe2O3 nanoparticles was prepared and characterized using transmission electron microscopy, scanning electron microscopy, and inductively coupled plasma atomic emission spectroscopy. The catalytic activity of the two prepared catalysts was compared in the synthesis of 1,8-dioxo-9,10-diaryldecahydroacridines in water. 12-Tungstophosphoric acid was highly dispersed on the silica-coated gamma-Fe2O3 nanoparticles and showed higher activity and a higher reuse number compared with the acid supported on aerosil silica. The catalyst could be recovered simply by using an external magnetic field and could be reused several times without appreciable loss of its catalytic activity. (C) 2013, Dalian Institute of Chemical Physics, Chinese Academy of Sciences. Published by Elsevier B.V. All rights reserved.