3,3,6,6-tetramethyl-9-(naphthalen-1-yl)-1,2,3,4,5,6,7,8,9,10-decahydroacridin-1,8-dione | 392722-22-4

• 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-(naphthalen-1-yl)-1,2,3,4,5,6,7,8,9,10-decahydroacridin-1,8-dione
• 英文别名: 3,3,6,6-Tetramethyl-9-naphthalen-1-yl-2,4,5,7,9,10-hexahydroacridine-1,8-dione
• CAS: 392722-22-4
• 化学式: C₂₇H₂₉NO₂
• 分子量: 399.533
• InChiKey: CSNXGZLETIFIIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  1-萘甲醛 、 5,5-二甲基-1,3-环己二酮 在 triphenyl(3-sulfopropyl)phosphonium trifluoromethanesulfonate 、 ammonium acetate 作用下， 以 neat (no solvent) 为溶剂， 反应 0.13h， 以96%的产率得到3,3,6,6-tetramethyl-9-(naphthalen-1-yl)-1,2,3,4,5,6,7,8,9,10-decahydroacridin-1,8-dione
  参考文献：
  名称：

  在可重复使用的绿色温和离子液体催化剂三苯基（丙基-3-磺酰基）三氟甲烷磺酸{[TPPSP] OTf}存在下，直接进行汉茨四和三组分缩合反应

  摘要：

  三氟甲烷磺酸三苯基（丙基-3-磺酰基）phosph（[TPPSP] OTf}可作为可重复使用的绿色和良性离子液体催化剂用于Hantzsch四组分（多氢喹啉的合成）和三组分（a啶的合成）缩合反应在无溶剂条件下，在室温下，在0.5 mol％的{[TPPSP] OTf}存在下，制备1,3-二酮，β-酮酸酯，醛，乙酸铵和苯胺衍生物。使用红外光谱，1 H NMR，13 C NMR，31 P NMR，19充分表征了新型离子液体催化剂F NMR和质谱，以及热重和衍生热重分析。另外，回收的催化剂可以在随后的反应中循环至少五次，而不会显着降低催化活性。与传统的合成方法相比，提出的新合成技术具有安全，条件温和，简单，反应时间短，收率高和后处理容易等诸多优点。首次报道了二十种产品。版权所有©2016 John Wiley＆Sons，Ltd.

  DOI：

  10.1002/aoc.3433

文献信息

• A convenient method for the synthesis of 1,8-dioxodecahydroacridine derivatives using 1-methylimidazolium tricyanomethanide {[HMIM]C(CN)3} as a nanostructured molten salt catalyst
  作者：Mohammad Ali Zolfigol、Neda Bahrami-Nejad、Saeed Baghery

  DOI：10.1016/j.molliq.2016.03.006

  日期：2016.6

  A practical and convenient method for the synthesis of 1,8-dioxodecahydroacridine derivatives was achieved via the one-pot condensation reaction of cyclic 1,3-diketone, aldehydes and various anilines or ammonium acetate in the presence of 1-methylimidazolium tricyanomethanide [HMIM]C(CN)3} as a nanostructured molten salt (NMS) catalyst at room temperature. In the present work, more than thirty products

  达到为1,8- dioxodecahydroacridine衍生物的合成的实用和方便的方法通过在1-甲基咪唑三氰基[HMIM存在环状1,3-二酮，醛和各种苯胺或乙酸铵的一锅缩合反应] C（CN）3 }在室温下为纳米结构熔盐（NMS）催化剂。在目前的工作中，将首次报告三十多种产品。
• Assessment and use of two silicon carbide multi-well plates for library synthesis and proteolytic digests using microwave heating
  作者：Lauren M. Stencel、Chad M. Kormos、Keri B. Avery、Nicholas E. Leadbeater

  DOI：10.1039/b902112d

  日期：——

  The use of two silicon carbide plates is reported for the preparation of three libraries of organic molecules using microwave heating. In addition, a preliminary study has been carried out, showing that one of the plates can also be used in a proteomics setting. Both the 24-position and 48-position plates heated evenly when irradiated with microwave energy. The 48-position plate was used to prepare a library of N-aryl functionalized β-amino esters via an aza-Michael reaction between anilines and Michael acceptors. The 24-position plate was used to prepare a library of biaryls via a Suzuki coupling methodology and a library of 1,4-dihydropyridines via a Hantzsch synthesis. The 48-position plate was also used to perform the proteolytic digestion of insulin chain B by trypsin.

  报道了使用两个碳化硅板通过微波加热制备三种有机分子库的方法。此外，还进行了初步研究，表明其中一个板材也可用于蛋白质组学环境。两个板材在微波辐射下均能均匀加热，即24位板和48位板。48位板被用于通过苯胺与迈克尔受体之间的氮迈克尔反应制备N-芳基功能化的β-氨基酯库。24位板被用于通过铃木偶联方法制备联苯库，以及通过汉奇合成制备1,4-二氢吡啶库。48位板还用于通过胰蛋白酶对胰岛素B链进行蛋白水解消化。
• MCM-41-SO3H as a nanoreactor for the one-pot, solvent-free synthesis of 1,8-dioxo-9-aryl decahydroacridines
  作者：Shahnaz Rostamizadeh、Asiyeh Amirahmadi、Nasrin Shadjou、Ali M. Amani

  DOI：10.1002/jhet.692

  日期：2012.1

  AbstractOne‐pot four‐component synthesis of 1,8‐dioxo‐9‐aryl decahydroacridines in solvent‐free condition was efficiently performed in the presence of MCM‐41‐SO3H as a nanocatalyst and nanoreactor in good yields. The method provides several advantages such as low cost, operational and experimental simplicity, high yields, and short reaction times. J. Heterocyclic Chem., (2012).