7-methoxy-3,3-dimethyl-3,4-dihydroacridin-1(2H)-one | 1569098-51-6

• 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: 7-methoxy-3,3-dimethyl-3,4-dihydroacridin-1(2H)-one
• CAS: 1569098-51-6
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: MDNPKOQJZJRZAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  39.19
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  7-methoxy-3,3-dimethyl-3,4,9,10-tetrahydroacridin-1(2H)-one 在 对苯醌 作用下， 以100%的产率得到7-methoxy-3,3-dimethyl-3,4-dihydroacridin-1(2H)-one
  参考文献：
  名称：

  One-Pot DBU-Promoted Synthesis of Hydroacridinones and Spirohexahydropyrimidines

  摘要：

  The potential hydroacridinone synthesis using simple and inexpensive starting materials, namely 1,3-dicarbonyl compounds, anilines, formaldehyde and DBU as a stoichiometric base was explored. As a result, from the reaction of 1,3-cyclohexanedione and dimedone tetrahydroacridinones were the main reaction products along with small yields of their oxidation products, the dihydroacridinones, whereas in the case of 2-acetylcyclohexanone spirohexahydropyrimidines were isolated in very good yields. Plausible mechanistic schemes for the formation of all products are proposed.

  DOI：

  10.1055/s-0033-1339922

文献信息

• CuSO₄–<scp>d</scp>-glucose, an inexpensive and eco-efficient catalytic system: direct access to diverse quinolines through modified Friedländer approach involving S_NAr/reduction/annulation cascade in one pot
  作者：Namrata Anand、Tanmoy Chanda、Suvajit Koley、Sushobhan Chowdhury、Maya Shankar Singh

  DOI：10.1039/c4ra14138e

  日期：——

  A one-pot, efficient approach to quinoline synthesis, directly from 2-bromoaromatic aldehydes/ketones in a H₂O–EtOH mixture involving a sequence of S_NAr/reduction/annulation cascade using CuSO₄-d-glucose, is devised.

  一种高效的一锅法制备喹啉的方法，直接从2-溴芳香醛/酮在H₂O–EtOH混合物中进行，涉及使用CuSO₄-d-葡萄糖的SNAr/还原/环化级联序列。
• Synthesis of quinolines via copper-catalyzed domino reactions of enaminones
  作者：Benyapa Kaewmee、Vatcharin Rukachaisirikul、Juthanat Kaeobamrung

  DOI：10.1039/c7ob01867c

  日期：——

  Quinoline derivatives were obtained from enaminones and 2-bromo- or 2-iodobenzaldehydes via copper-catalyzed domino reactions consisting of the Aldol reaction, C(aryl)-N bond formation and elimination. The electronic effect of aldehydes played a major role in the reaction outcome. Two simple protocols are disclosed to achieve variuos quinolines from both cyclic and acyclic enaminones in good yields

  喹啉衍生物是通过铜催化的由Aldol反应，C（芳基）-N键的形成和消除组成的多米诺反应从烯胺酮和2-溴-或2-碘代苯甲醛中获得的。醛的电子效应在反应结果中起主要作用。公开了两种简单的方案以良好的收率从环状和无环烯胺酮两者获得变异喹啉。对于反应性较低的无环烯胺酮，表明2-（2-溴苄叉基）丙二酸二乙酯比苯甲醛更具相容性。
• Domino Nitro Reduction-Friedländer Heterocyclization for the Preparation of Quinolines
  作者：Kwabena Fobi、Richard A. Bunce

  DOI：10.3390/molecules27134123

  日期：——

  presence of active methylene compounds (AMCs) to produce substituted quinolines in high yields. The conditions are mild enough to tolerate a wide range of functionality in both reacting partners and promote reactions not only with phenyl and benzyl ketones, but also with β-keto-esters, β-keto-nitriles, β-keto-sulfones and β-diketones. The reaction of 2-nitroaromatic ketones with unsymmetrical AMCs is

  Friedländer 合成提供了在碱存在下从 2-氨基苯甲醛和活化酮中高效获得取代喹啉的途径。该方法的缺点在于容易获得的 2-氨基苯甲醛衍生物相对较少。为了克服这个问题，我们报告了这一过程的改进，包括在活性亚甲基化合物 (AMC) 存在下用 Fe/AcOH 原位还原 2-硝基苯甲醛，以高产率生产取代的喹啉。该条件足够温和，可以耐受反应伙伴中的广泛功能，并促进不仅与苯基和苄基酮的反应，而且还与 β-酮酯、β-酮腈、β-酮砜和 β-二酮。2-硝基芳族酮与不对称 AMC 的反应不太可靠，H )-ones 来自Z Knoevenagel 中间体的环化，当某些大基团与 AMC 酮羰基相邻时，这似乎是有利的。