9-(p-dimethylaminophenyl)-3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione | 3476-94-6

• 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: 9-(p-dimethylaminophenyl)-3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione
• 英文别名: 9‑(4‑dimethylaminophenyl)‑3,3,6,6‑tetramethyl‑3,4,6,7,9,10‑hexahydroacridine‑1,8(2H,5H)‑dione；3,3,6,6‑tetramethyl‑9‑(4‑N,N‑dimethylphenyl)‑1,8‑dioxodecahydroacridine；9-(4-(dimethylamino)phenyl)-3,3,6,6-tetramethyl-3,4,6,7-tetrahydroacridine-1,8(2H,5H,9H,10H)-dione；9-(4-(dimethylamino)phenyl)-3,4,6,7(2H,5H,9H,10H)-tetrahydro-3,3,6,6-tetramethylacridine-1,8-dione；9-(4-(dimethylamino)phenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione；9-(4-dimethylaminophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro-(2H,5H)-acridine-1,8-dione；9-(4-Dimethylaminophenyl) 3,4,6,9,10-hexahydro 2,2,8,8-tetramethyl 1,8(2H,5H)-acridine dione；9-[4-(dimethylamino)phenyl]-3,3,6,6-tetramethyl-2,4,5,7,9,10-hexahydroacridine-1,8-dione
• CAS: 3476-94-6
• 化学式: C₂₅H₃₂N₂O₂
• mdl: MFCD00511320
• 分子量: 392.541
• InChiKey: UPWDRMNSCSOBKI-UHFFFAOYSA-N

物化性质

• 熔点：
  264-266 °C
• 沸点：
  559.0±50.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-(p-dimethylaminophenyl)-3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione 以 溶剂黄146 为溶剂， 反应 1.0h， 以85%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:1017668408493
• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 1.78h， 生成 9-(p-dimethylaminophenyl)-3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione
  参考文献：
  名称：

  Efficient synthesis of decahydroacridine-1,8-diones and polyhydroquinolines using the step-wise method

  摘要：

  通过两步环化缩合反应合成了多种对称的和非对称的十氢吖啶-1,8-二酮和多氢喹啉衍生物。与其它一步合成反应相比，逐步加入反应物的优势在于避免形成2或3个不希望的副产品，从而实现了更清洁的反应处理。这种高效环化缩合方法的关键因素是，将制备的β-烯胺酮组分逐滴加入到溶液中，在该溶液中醛分子与1,3-二羰基化合物反应逐渐形成Knoevenagel缩合产物。将提出的逐步方法的结果与一步合成反应所得结果进行比较和讨论。

  DOI：

  10.1007/s11164-021-04643-z

文献信息

• A Novel Reaction of Aldeoxime with Dimedone Under Microwave Irradiation
  作者：Shujang Tu、Yuan Gao、Chunbao Miao、Tuanjie Li、Xiaojing Zhang、Songlei Zhu、Fang Fang、Daqing Shi

  DOI：10.1081/scc-120030317

  日期：2004.12.31

  Abstract The reaction of aldeoxime with dimedone and ammonium acetate in glycol under microwave irradiation has been carried out, elimination and cyclization happened and acridine derivatives were obtained. The structure of the product has been thoroughly studied by x‐ray crystallographic analysis.

  摘要 在微波辐射下，醛肟与二甲酮和乙酸铵在乙二醇中反应，发生消除环化反应，得到吖啶衍生物。产品的结构已经通过 X 射线晶体学分析进行了彻底的研究。
• 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。

• Melamine-formaldehyde resin supported H⁺-catalyzed three-component synthesis of 1,8-dioxo-decahydroacridine derivatives in water and under solvent-free conditions
  作者：Ramin Rezaei、Reza Khalifeh、Maryam Rajabzadeh、Liela Dorosty、Mohammad Mahdi Doroodmand

  DOI：10.1515/hc-2012-0053

  日期：2013.3.1

  Abstract A convenient and practical synthesis of 1,8-dioxo-decahydroacridine derivatives using various aldehydes, 5,5-dimethyl-1,3-cyclohexanedione and thiourea in water, was successfully carried out in the presence of melamine-formaldehyde resin supported H+ (MFRH) as a catalyst. Under solvent-free conditions, rapid and efficient synthesis of 1,8-dioxo-decahydroacridine and N-substituted 1,8-dioxo-decahydroacridine

  摘要 在三聚氰胺-甲醛树脂负载的 H+ 存在下，使用各种醛、5,5-二甲基-1,3-环己二酮和硫脲在水中方便实用地合成了 1,8-二氧十氢吖啶衍生物（ MFRH) 作为催化剂。在无溶剂条件下，以醋酸铵和芳香胺为氮源，也可以快速高效地合成1,8-二氧十氢吖啶和N-取代的1,8-二氧十氢吖啶衍生物。
• Carbon-based nanocatalyst: An efficient and recyclable heterogeneous catalyst for one-pot synthesis of gem-bisamides, hexahydroacridine-1,8-diones and 1,8-dioxo-octahydroxanthenes
  作者：Jaspreet Kour、Monika Gupta、Bushra Chowhan、Vivek K. Gupta

  DOI：10.1007/s13738-019-01723-1

  日期：2019.12

  acid as a solid acid catalyst. This nanocatalyst is recyclable and also exhibited very high activity. Novel carbon-based nanocatalyst, i.e. cellulose[2-(sulfooxy)ethyl]mercaptosulfonic acid[SEMSA] was successfully synthesized by reacting mercaptoethanol and chlorosulfonic acid, and the catalytic activity of the prepared catalysts was evaluated for the one-pot synthesis of gem-bisamides from various aldehydes

  摘要在此摘要中，我们讨论了磺化碳基材料在各种酸催化的有机转化中的进展，然后将其进一步应用于医学领域，实验室和工业中。采用一种简单新颖的方法制备了碳基纳米催化剂，即纤维素[2-（磺氧基）乙基]巯基磺酸作为固体酸催化剂。该纳米催化剂是可回收的，并且还表现出非常高的活性。巯基乙醇与氯磺酸反应成功合成了新型的碳纳米催化剂纤维素[2-（磺氧基）乙基]巯基磺酸[SEMSA]，并评价了所制备催化剂的催化活性，用于一锅法合成宝石。-通过醛和二甲酮与芳族醛，二甲酮和乙酸铵或芳香胺和1,8-二氧-八氢氧杂蒽的三组分缩合，可得自各种醛和苯甲酰胺的双酰胺，六氢ac啶-1,8-二酮。与传统的合成方法相比，这种新的非均相纳米催化剂系统的应用具有高收率，反应时间短，生态友好，操作简便的优点，并且已通过1 H等研究确定了合成产物核磁共振和131 H NMR。在各种催化剂中，发现该纳米催化剂，即纤维素[2-（磺氧基）乙基]
• Novel Brønsted Acidic Ionic Liquid ([CMIM][CF3COO]) Prompted Multicomponent Hantzsch Reaction for the Eco-Friendly Synthesis of Acridinediones: An Efficient and Recyclable Catalyst
  作者：Dayanand Patil、Dattatray Chandam、Abhijeet Mulik、Prasad Patil、Surybala Jagadale、Rajni Kant、Vivek Gupta、Madhukar Deshmukh

  DOI：10.1007/s10562-014-1202-z

  日期：2014.5

  AbstractsA novel, highly efficient and recyclable Brønsted acidic ionic liquid ([CMIM][CF3COO]) has been successfully implemented for the synthesis of acridinediones in aqueous media. Recyclability of novel catalyst, high yields, use of environmentally benign aqueous media as solvent, simple product isolation, high atom economy and sidestep to column chromatography are the noteworthy features of this

  摘要：一种新型、高效且可回收的布朗斯台德酸性离子液体 ([CMIM][CF3COO]) 已成功用于在水性介质中合成吖啶二酮。新型催化剂的可回收性、高产率、使用对环境无害的水性介质作为溶剂、产品分离简单、原子经济性高和对柱色谱的回避是该协议的显着特点。该协议能够以良好到出色的产量生产广泛的吖啶二酮库。此外，通过单晶 X 射线衍射证实了 4c 和 4s 衍生物的分子结构和相对立体化学。