3-methyl-10H-acridin-9-one | 57165-19-2

• 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-methyl-10H-acridin-9-one
• 英文别名: 3-methyl-acridin-9(10H)-one；3-methylacridin-9(10H)-one；3-methylacridone；3-methyl-10H-acridin-9-one；3-Methyl-10H-acridin-9-on；3-methyl-9-acridanone；6-Methyl-acridone
• CAS: 57165-19-2
• 化学式: C₁₄H₁₁NO
• 分子量: 209.247
• InChiKey: MFWDQDXQUXODPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methyl-10H-acridin-9-one 在 氢氧化钾 、 苄基三乙基氯化铵 、 potassium carbonate 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 60.0h， 生成 10-But-3-en-1-ynyl-3-methyl-10H-acridin-9-one
  参考文献：
  名称：

  Phase-Transfer-Catalysed Alkylative Elimination: Synthesis of 10-Enynyl Acridones from Acridones and 1-Aryloxy-4-chlorobut-2-ynes

  摘要：

  A number of hitherto unreported 1O-enynylacridones (4a-f) were obtained in good yields by refluxing 10-(4-aryloxybut-2-ynyl) acridones (3a-f) with benzyltriethylamonium chloride (BTEAC) and aqueous potassium hydroxide (50%) in toluene or directly from acridones (1) and 1-aryloxy-4-chlorobut-2-ynes (5) under the same reaction conditions.

  DOI：

  10.1080/00397919408013821
• 作为产物：
  描述：

  3-甲基环己酮 在 三氯氧磷 作用下， 反应 0.15h， 生成 3-methyl-10H-acridin-9-one
  参考文献：
  名称：

  Tetrahydroacridin-9-ones, 9-chlorotetrahydroacridines, 9-amino-tetrahydroacridines and 9-(pyrazol-1-yl)-tetrahydroacridines derived from chiral cyclanones

  摘要：

  A series of tetrahydroacridines related to tacrine have been synthesized starting from 3-methylcyclohexananone, menthone, pulegone, carvone and dihydrocarvone (both racemic and chiral). In many cases, the yields and purity of the compounds have been improved by the use of a microwave oven. These compounds have been characterized by H-1 and C-13 NMR data. To establish their relative configuration, the structure of (1R,4R)-(+)-9-chloro-1-methyl-4-isopropyl-1,2,3,4-tetrahydroacridine (cis-10b), derived from (2S,5R)-(-)-menthone, has been determined by X-ray. The chemical shifts of cis-10b and trans-10b have been calculated at the GIAO/B3LYP/6-31G* level and compared successfully with the experimental data. (C) 2003 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2003.10.003

文献信息

• Access to acridones by tandem copper(<scp>i</scp>)-catalyzed electrophilic amination/Ag(<scp>i</scp>)-mediated oxidative annulation of anthranils with arylboronic acids
  作者：Chun-Yong Jiang、Hui Xie、Zhuo-Jun Huang、Jing-Yi Liang、Yan-Xia Huang、Qiu-Ping Liang、Jun-Yi Zeng、Binhua Zhou、Shang-Shi Zhang、Bing Shu

  DOI：10.1039/d1ob01586a

  日期：——

  An efficient and practical approach for the synthesis of medicinally important acridones was developed from anthranils and commercially available arylboronic acids by a tandem copper(I)-catalyzed electrophilic amination/Ag(I)-mediated oxidative annulation strategy. This new and straightforward protocol displayed a broad substrate scope (25 examples) and high functional group tolerance. What's more

  通过串联铜（）催化的亲电胺化/银（）介导的氧化环化策略，从邻氨基苯甲醚和市售芳基硼酸开发了一种有效且实用的合成药用重要吖啶酮的方法。这种新的、简单的方案显示了广泛的底物范围（25 个示例）和高官能团耐受性。此外，还提出了一种可能的机制建议。
• Dimethyl sulfoxide-aided copper(0)-catalyzed intramolecular decarbonylative rearrangement of N-aryl isatins leading to acridones
  作者：Hao Wu、Nana Ma、Mengxiao Song、Guisheng Zhang

  DOI：10.1016/j.cclet.2019.10.043

  日期：2020.6

  Abstract Described here is the first example of Cu(0)-catalyzed intramolecular decarbonylative rearrangements of readily available N-aryl isatins assisted by solvent dimethyl sulfoxide (DMSO) under air atmosphere and additive-free conditions leading to various biologically important acridones in good to excellent yields. This novel transformation is proposed to go through a sequential DMSO-aided Cu

  摘要本文描述了在空气气氛和无添加剂条件下，Cu（0）催化易得的N-芳基isatins在溶剂和无添加剂条件下通过Cu（0）催化的分子内脱羰重排的第一个例子，导致各种重要的生物学上重要的good啶类化合物产量。提出了这种新颖的转化方法，该方法需要通过依次进行DMSO辅助的Cu插入酰胺CN键，CO挤出，Cu迁移，还原消除和DMSO辅助的质子迁移过程，在单个化学步骤中涉及多种类型的键裂解和形成。 。
• Copper-Catalyzed Aerobic Oxidative CH and CC Functionalization of 1-[2-(Arylamino)aryl]ethanones Leading to Acridone Derivatives
  作者：Jipan Yu、Haijun Yang、Yuyang Jiang、Hua Fu

  DOI：10.1002/chem.201204169

  日期：2013.3.25

  Efficient copper‐catalyzed aerobic oxidative CH and CC functionalization of 1‐[2‐(arylamino)aryl]ethanones leading to acridones has been developed. The procedure involves cleavage of aromatic CH and acetyl CC bonds with intramolecular formation of a diarylketone bond. The protocol uses inexpensive Cu(O2CCF3)2 as catalyst, pyridine as additive, and economical and environmentally friendly oxygen

  已经开发出有效的铜催化需氧氧化CH和CC功能化的1- [2-（芳基氨基）芳基]乙炔导致a啶酮。该过程涉及的切割芳族C  H和乙酰Ç  C键与分子内形成一个二芳基键的。该方案使用廉价的Cu（O 2 CCF 3）2作为催化剂，吡啶作为添加剂，经济和环境友好的氧气作为氧化剂，并以中等至良好的收率获得了具有各种官能团的相应的cri啶。
• Syntheses of Acridones via Copper(II)-Mediated Relay Reactions from <i>o</i>-Aminoacetophenones and Arylboronic Acids
  作者：Hao Wu、Zhiguo Zhang、Qingfeng Liu、Tongxin Liu、Nana Ma、Guisheng Zhang

  DOI：10.1021/acs.orglett.8b00957

  日期：2018.5.18

  The reaction of o-aminoacetophenones and arylboronic acids catalyzed by copper(II) salts in the presence of pyridine under an O2 atmosphere provides a general and efficient one-pot preparation of biologically interesting acridones. This relay reaction comprises an intermolecular Suzuki cross-coupling, intramolecular oxidative C(sp3)–H amination, and C(sp2)–H activation with simultaneous rearrangement

  在吡啶存在下，在O 2气氛下，铜（II）盐催化的邻氨基苯乙酮与芳基硼酸的反应提供了一种通用且有效的一锅法制备的生物学上令人感兴趣的don啶。此中继反应包括分子间Suzuki交叉偶联，分子内氧化C（sp 3）-H氨基化和C（sp 2）-H活化，同时重排生成的靛红中间体。该策略容许给电子和提取功能，从而以良好或优异的产率提供各种a啶。
• Copper-catalyzed C–C bond cleavage and intramolecular cyclization: an approach toward acridones
  作者：Wang Zhou、Youqing Yang、Yong Liu、Guo-Jun Deng

  DOI：10.1039/c2gc36502b

  日期：——

  A copper-catalyzed approach for the synthesis of acridones via C–C bond cleavage and intramolecular cyclization using air as the oxidant under neutral conditions is described. This transformation offers an alternative method to prepare medicinally important acridones and a new strategy for C–C bond cleavage.

  为吖啶酮的合成的铜催化的方法通过C-C键断裂和分子内环化描述了在中性条件下使用空气作为氧化剂。这种转变为制备具有重要医学意义的cri啶酮提供了另一种方法，并为CC键断裂提供了新的策略。