1,2,3-Trimethoxy-N-methylacridon | 13082-16-1

• 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: 1,2,3-Trimethoxy-N-methylacridon
• 英文别名: 1,2,3-Trimethoxy-10-methylacridin-9(10h)-one；1,2,3-trimethoxy-10-methylacridin-9-one
• CAS: 13082-16-1
• 化学式: C₁₇H₁₇NO₄
• 分子量: 299.326
• InChiKey: JZITVQGPQMLTPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2,3-Trimethoxy-N-methylacridon 在 盐酸 、 硝酸 作用下， 生成 3-methoxy-10-methyl-10H-acridine-1,2,9-trione
  参考文献：
  名称：

  Hughes; Neill, Australian Journal of Scientific Research, Series A: Physical Sciences, 1949, vol. 2, p. 429,436

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,4-trimethoxy-6-nitrobenzoic acid 在 platinum(IV) oxide 、 palladium on activated charcoal sodium hydroxide 、 正丁基锂 、 氢气 、 sodium hydride 、 二异丙胺 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 甲苯 、 xylene 为溶剂， -78.0~25.0 ℃ 、275.79 kPa 条件下， 反应 8.5h， 生成 1,2,3-Trimethoxy-N-methylacridon
  参考文献：
  名称：

  Coppola, Gary M.; Schuster, Herbert F., Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 957 - 964

  摘要：

  DOI：

文献信息

• Copper-Catalyzed Intramolecular Oxidative CH Functionalization and CN Formation of 2-Aminobenzophenones: Unusual Pseudo-1,2-Shift of the Substituent on the Aryl Ring
  作者：Pang-Chi Huang、Kanniyappan Parthasarathy、Chien-Hong Cheng

  DOI：10.1002/chem.201203859

  日期：2013.1.7

  A good move: A copper‐catalyzed intramolecular oxidative CH functionalization of 2‐aminobenzophenone affords two regioisomeric acridones (see scheme). The reaction involves an unusual pseudo‐1,2‐migration of R2 group(s) on the arene ring (bpy=2,2′‐bipyridine, DMAc=dimethylacetimide).

  一个好方法：铜催化的2-氨基二苯甲酮的分子内氧化CH功能化可提供两个区域异构的cri啶（参见方案）。该反应涉及芳烃环上的R 2基团异常的假1,2-迁移（bpy = 2,2'-联吡啶，DMAc =二甲基乙酰亚胺）。
• Use of N-lithiated ethyl anthranilates as 1,4-dipole equivalents in 1,4-dipolearyne cycloaddition: A novel approach to the synthesis of acridones
  作者：Subhash P. Khanapure、Baburao M. Bhawal、Edward R. Biehl

  DOI：10.1016/0040-4039(90)80169-m

  日期：1990.1

  A new strategy for acridones based on 1,4-dipolar cycloaddition of N-lithiated ethyl anthranilates, which function as 1,4-dipole equivalents, with arynes is reported.

  报道了基于N-锂化邻氨基苯甲酸乙酯的1，4-偶极环加成的a啶酮的新策略，其与芳烃起1，4-偶极当量的作用。
• Weakly Coordinating, Ketone-Directed (η⁵ -Pentamethylcyclopentadienyl)cobalt(III)- and (η⁵ -Pentamethylcyclopentadienyl)rhodium(III)-Catalyzed C−H Amidation of Arenes: A Route to Acridone Alkaloids
  作者：Sourav Sekhar Bera、Md Raja Sk、Modhu Sudan Maji

  DOI：10.1002/chem.201805376

  日期：2019.2.1

  monoamidation of aromatic ketones, chalcone, carbazole, and benzophenones was achieved by employing high‐valent cobalt and rhodium catalysis to access numerous biologically important molecular building blocks. This amidation proceeded smoothly with a variety of ketones and several amidating partners. The application of the products in the synthesis of various heterocycles, including acridones, indoles, quinoline

  芳香族酮，查尔酮，咔唑和二苯甲酮的弱配位，酮定向，区域选择性单酰胺化是通过使用高价钴和铑催化作用来获得许多生物学上重要的分子构件而实现的。该酰胺化反应与各种酮和一些酰胺化伙伴一起进行得很顺利。还研究了产物在各种杂环的合成中的应用，包括including啶，吲哚，喹啉，喹诺酮，喹啉酮和喹唑啉。通过这种方法，也可以完成基于cri啶酮的生物碱的总合成，即托达洛辛A，托达洛辛D和Arborinine，以及正式合成了丙烯醛和诺拉霉素。
• A Novel Palladium-Based Heterogeneous Catalyst for Tandem Annulation: A Strategy for Direct Synthesis of Acridones
  作者：Darío C. Gerbino、H. Sebastián Steingruber、Pamela Mendioroz、M. Julia Castro、María A. Volpe

  DOI：10.1055/s-0042-1751371

  日期：2023.2

  In order to develop an efficient, rapid, and modular cascade strategy for the direct synthesis of acridones, palladium supported on sulfated alumina and microwave activation are employed. Multifunctional heterogeneous palladium catalysts were prepared in order to carry out the sequential annulation via a Buchwald–Hartwig amination followed by an intramolecular annulation in a one-pot process. This

  为了开发用于直接合成吖啶酮的高效、快速和模块化级联策略，采用负载在硫酸化氧化铝上的钯和微波活化。制备了多功能非均相钯催化剂，以通过 Buchwald-Hartwig 胺化进行顺序环化，然后在一锅法中进行分子内环化。这一新协议代表了第一份关于在无配体条件下从市售起始材料催化串联合成吖啶酮衍生物的报告。本方法的范围扩展到生成功能化吖啶酮文库，显示出高官能团兼容性，产率适中至极好。
• Synthesis of novel heme-interacting acridone derivatives to prevent free heme-mediated protein oxidation and degradation
  作者：Chinmay Pal、Milan Kumar Kundu、Uday Bandyopadhyay、Susanta Adhikari

  DOI：10.1016/j.bmcl.2011.04.127

  日期：2011.6

  Heme is an important prosthetic molecule for various hemoproteins and serves important function in living aerobic organisms. But degradation of hemoprotein, for example, hemoglobin during different pathological conditions leads to the release of heme, which is very toxic as it induces oxidative stress and inflammation due to its pro-oxidant nature. Thus, synthesis of compound that will detoxify free heme by interacting with it would be fruitful for the management of heme-induced pathogenesis. Here, we report the synthesis of a novel natural product arborinine and some other acridone derivatives, which interact with free heme. These acridones in vitro block heme-mediated protein oxidation and degradation, markers for heme-induced oxidative stress. (C) 2011 Elsevier Ltd. All rights reserved.