3,3-dimethyl-9-(4-hydroxy-3-methoxyphenyl)-1,2,3,4,9,10-hexahydrobenzo[c]acridine-1-one

• 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-dimethyl-9-(4-hydroxy-3-methoxyphenyl)-1,2,3,4,9,10-hexahydrobenzo[c]acridine-1-one
• 英文别名: 10,10-dimethyl-7-(4-hydroxy-3-methoxyphenyl)-7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one；7-(4-hydroxy-3-methoxyphenyl)-10,10-dimethyl-7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one；7-(4-hydroxy-3-methoxyphenyl)-10,10-dimethyl-7,9,11,12-tetrahydronaphtho[1,2-b]quinolin-8-one
• 化学式: C₂₆H₂₅NO₃
• 分子量: 399.489
• InChiKey: BATCJNQHQPKXCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-萘胺 、 5,5-二甲基-1,3-环己二酮 、 香草醛 以 乙醇 为溶剂， 以68%的产率得到3,3-dimethyl-9-(4-hydroxy-3-methoxyphenyl)-1,2,3,4,9,10-hexahydrobenzo[c]acridine-1-one
  参考文献：
  名称：

  二甲酮、芳基醛和 1-萘胺之间的新型双三组分和五组分反应：合成和计算研究

  摘要：

  用于合成吖啶和双(2-苄基-5,5-二甲基环己烷-1,3-二酮)-N-和4-二取代的一系列单锅、原子经济、平行三组分和五组分反应已经研究了二甲酮、芳基醛和 1-萘胺在绿色条件下的萘胺衍生物。合成吖啶衍生物的三组分路线是众所周知的，但五组分路线导致双(2-苄基-5,5-二甲基环己烷-1,3-二酮)-N-和4-二取代萘胺衍生物，这是一种前所未有的途径，本文首次报道。通过这一成就，已经合成了广泛的新型吖啶和双（2-苄基-5,5-二甲基环己烷-1,3-二酮）-N-和4-二取代萘胺衍生物，并在此期间取得了可观的成绩。计算机分析，包括分子对接、分子动力学和 ADMET 预测工具。吖啶衍生物和N ,4-二取代萘胺似乎分别与 5-HT 2A/C和 MAO-A/B 显着相互作用。

  DOI：

  10.1016/j.molstruc.2022.132569

文献信息

• An efficient one-pot synthesis of polyhydrobenzoacridine-1-one derivatives under microwave irradiation without catalyst
  作者：Shujiang Tu、Runhong Jia、Bo Jiang、Yan Zhang、Junyong Zhang

  DOI：10.1002/jhet.5570430629

  日期：2006.11

  A series of 3,3-dimethyl-9-substituted-1,2,3,4,9,10-hexahydrobenzo[c] acridine-1-ones and 3,3-dimethyl-9-substituted-1,2,3,4,9,10-hexahydrobenzo[a] acridine-1-ones were synthesized by the reaction of an aldehyde, α-naphthylamine or β-naphthylamine and dimedone under microwave irradiation with short times and high yields.

  一系列3,3-二甲基-9-取代的1,2,3,4,9,10-六氢苯并[ c ] a啶-1-酮和3,3-二甲基-9-取代的1,2,3通过醛，α-萘胺或β-萘胺与二甲酮在微波辐射下短时间，高收率反应合成了4,9,10-六氢苯并[ a ] a啶-1-酮。
• Ultrasound-Promoted One-Pot Synthesis of 7-Aryl-7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one Derivatives
  作者：Hongjun Zang、Yong Zhang、Yingming Mo、Bowen Cheng

  DOI：10.1080/00397911.2010.517610

  日期：2011.11.1

  A series of 7-aryl-7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one derivatives were synthesized via the three-component coupling from aromatic aldehydes, 1-naphthylamine, and 5,5-dimethylcyclohexane-1,3-dione catalyzed by stannous chloride dihydrate (SnCl2 center dot 2H(2)O) under ultrasonic irradiation at room temperature. The products were isolated in good yields within short reaction times.
• An efficient ultrasound-promoted method for the one-pot synthesis of 7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one derivatives
  作者：Hongjun Zang、Yong Zhang、Yaping Zang、Bo-Wen Cheng

  DOI：10.1016/j.ultsonch.2009.11.003

  日期：2010.3

  A new, efficient and general method for preparation of 7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one derivatives using ultrasound irradiation is reported. Under ultrasound, the reaction time is short, the yields are high and the reaction conditions are mild. (c) 2009 Elsevier B.V. All rights reserved.