1-methylacridin-9(10H)-one | 65753-71-1

• 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-methylacridin-9(10H)-one
• 英文别名: 1-Methyl-9(10H)-acridinone；1-methyl-10H-acridin-9-one
• CAS: 65753-71-1
• 化学式: C₁₄H₁₁NO
• 分子量: 209.247
• InChiKey: CVLMVMQNJODBLJ-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：

  1-methylacridin-9(10H)-one 在 lithium aluminium tetrahydride 、 TiCl₃(THF)₃ 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 1-methyl-9-(tricyclo[3.3.1.1^3,7]dec-2-ylidene)-10(9H)-acridineacetic acid ethyl ester
  参考文献：
  名称：

  Preparation and Characterization of Thermochemiluminescent Acridine-Containing 1,2-Dioxetanes as Promising Ultrasensitive Labels in Bioanalysis

  摘要：

  Thermochemiluminescence is the luminescence process in which a thermodynamically unstable molecule decomposes with light emission when heated above a threshold temperature. We recently reported the thermochemiluminescence properties of an acridine-containing 1,2-dioxetane, which emits at relatively low temperatures (i.e., below 100 degrees C). Herein, we explored the effect of the introduction of methyl substituents in the acridine system. The methyl group did not determine an excessive destabilization of 1,2-dioxetane ring nor significantly affect the general physical properties of the molecule. Monosubstituted methyl derivatives and a series of derivatives bearing several combinations of two, three, and four methyl groups were prepared. The rate of formation of 1,2-dioxetane derivatives 1b-k strongly depended on the methyl substitution pattern. All members of this library of mono-, di-, tri-, and tetramethyl-substituted derivatives were characterized in terms of photophysical and thermochemiluminescence properties. The introduction of methyl groups into the acridine ring caused a marked decrease in the activation energy of the thermochemiluminescent reaction. Tri- and tetramethyl-substituted acridones had the highest fluorescence quantum yields, in the range 0.48-0.52, and the corresponding 1,2-dioxetanes 1h and 1j showed in thermochemiluminescence imaging experiments limit of detection values more than ten times lower with respect to the unsubstituted derivative.

  DOI：

  10.1021/jo401683r
• 作为产物：
  描述：

  2-苯胺基-6-甲基-苯甲酸 在 三氯氧磷 作用下， 生成 1-methylacridin-9(10H)-one
  参考文献：
  名称：

  Gleu; Nitzsche, Journal fur praktische Chemie (Leipzig 1954), 1939, vol. <2> 153, p. 200,213

  摘要：

  DOI：

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。
• 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。
• Lehmstedt, Chemische Berichte, 1932, vol. 65, p. 834,838, 999, 1005
  作者：Lehmstedt

  DOI：——

  日期：——