2,7-dimethylacridin-9(10H)-one | 24212-76-8

• 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: 2,7-dimethylacridin-9(10H)-one
• 英文别名: 2,7-dimethyl-10H-acridin-9-one
• CAS: 24212-76-8
• 化学式: C₁₅H₁₃NO
• 分子量: 223.274
• InChiKey: IBEGAUGEWHXHQH-UHFFFAOYSA-N

物化性质

• 沸点：
  402.6±45.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  2,7-dimethylacridin-9(10H)-one 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 9-chloro-2,7-dimethylacridine
  参考文献：
  名称：

  Syntheses and Evaluation of New Bisacridine Derivatives for Dual Binding of G-Quadruplex and i-Motif in Regulating Oncogene c-myc Expression

  摘要：

  The c-myc oncogene is an important regulator for cell growth and differentiation, and its aberrant overexpression is closely related to the occurrence and development of various cancers. Thus, the suppression of c-myc transcription and expression has been investigated for cancer treatment. In this study, various new bisacridine derivatives were synthesized and evaluated for their binding with c-myc promoter G-quadruplex and i-motif. We found that a9 could bind to and stabilize both G-quadruplex and i-motif, resulting in the downregulation of c-myc gene transcription. a9 could inhibit cancer cell proliferation and induce SiHa cell apoptosis and cycle arrest. a9 exhibited tumor growth inhibition activity in a SiHa xenograft tumor model, which might be related to its binding with c-myc promoter G-quadruplex and i-motif. Our results suggested that a9 as a dual G-quadruplex/i-motif binder could be effective in both oncogene replication and transcription and become a promising lead compound for further development with improved potency and selectivity.

  DOI：

  10.1021/acs.jmedchem.9b01917
• 作为产物：
  描述：

  2-碘-5-甲基苯甲酸 在 N-甲基吗啉 、 copper(I) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 生成 2,7-dimethylacridin-9(10H)-one
  参考文献：
  名称：

  酸催化吖啶与甲硅烷基重氮烯醇化物的氧化交叉偶联和Rh催化重排：γ-(9-吖啶亚基)-β-酮酯的两步合成

  摘要：

  描述了吖啶类和甲硅烷基重氮烯醇化物的 MsOH 催化的氧化交叉偶联和所得重氮产物的 Rh 2 (OAc) 4催化的重排。该反应以良好的收率提供了各种 γ-(9-acridanylidene)-β-酮酯，它们带有一个活性 α-亚甲基单元用于进一步的官能化。

  DOI：

  10.1039/d1ob00691f

文献信息

• Bridged Organosilane and Production Method Thereof
  申请人：Shimada Toyoshi

  公开号：US20090054649A1

  公开（公告）日：2009-02-26

  Provided is a bridged organosilane, which has a large complex organic group, and which is useful in the synthesis of a mesoporous silica and a light-emitting material, and a production method of the bridged organosilane. The bridged organosilane is expressed by the following general formula (1): [in the formula (1), q represents an integer in a range from 2 to 4, X 1 — represents a substituent selected from the group consisting of substituents expressed by the following general formulae (2) to (5): (in the formulae (2) to (5), R 1 represents alkyl group having 1 to 5 carbon atoms, R 2 represents an allyl group, and n represents an integer in a range from 0 to 3, and m represents an integer in a range from 0 to 6), and A 1 represents an organic group expressed by, for example, the following general formula (6): (in the formula (6), Y 1 < represents a substituent expressed by, for example, O═C<)].

  提供的是一种桥联有机硅烷，其具有一个大的复杂有机基团，可用于合成介孔二氧化硅和发光材料，以及一种桥联有机硅烷的生产方法。该桥联有机硅烷由以下通用式（1）表示：[在式（1）中，q表示一个范围为2到4的整数，X1—表示从由以下通用式（2）到（5）表示的取代基组成的群中选择的取代基（在式（2）到（5）中，R1表示具有1到5个碳原子的烷基，R2表示烯丙基，n表示一个范围为0到3的整数，m表示一个范围为0到6的整数），A1表示由例如以下通用式（6）表示的有机基团（在式（6）中，Y1<表示由例如O═C<表示的取代基）]。
• 一种利用钯-铜共催化合成吖啶酮衍生物的方 法
  申请人：武汉大学

  公开号：CN106187890B

  公开（公告）日：2018-09-21

  本发明公开了一种利用钯‑铜共催化合成吖啶酮衍生物的方法，在氯化钯、特戊酸铜和过氧化二叔丁基或氧气共同存在的条件下，将二苯胺类化合物(包括对称和不对称二苯胺)溶于无水有机溶剂中，混合均匀，然后在一氧化碳氛围、80‑120℃条件下反应20‑30小时，分离纯化，即可得吖啶酮衍生物。本发明制备方法简单，使用简单易得的二苯胺类化合物为原料，通过C‑H/C‑H氧化羰基化直接构建吖啶酮衍生物；其制备条件温和，在80‑120℃下就能高选择性地得到目标产物；且本发明具有很好的底物适用性，大大地拓展了底物的范围，在生物医药、材料等方面具有很大的应用前景。
• Palladium/Copper Co-catalyzed Oxidative C–H/C–H Carbonylation of Diphenylamines: A Way To Access Acridones
  作者：Jiangwei Wen、Shan Tang、Fan Zhang、Renyi Shi、Aiwen Lei

  DOI：10.1021/acs.orglett.6b03356

  日期：2017.1.6

  palladium/copper co-catalyzed oxidative double C(sp2)–H functionalization/carbonylation of diphenylamines for synthesis of acridones has been developed. This method utilizes readily available starting materials and mild reaction conditions. The protocol provides a simple, efficient, and atom-economic way to access acridones. Notably, the present protocol has excellent functional group tolerance and application

  已经开发了一种有效的钯/铜共催化二苯胺的氧化双C（sp 2）-H官能化/羰基化合成a啶酮。该方法利用了容易获得的起始原料和温和的反应条件。该协议提供了一种简单，有效且经济实惠的方式来获取a烯。值得注意的是，本协议具有优异的官能团耐受性和应用价值。
• Simultaneous production of p-tolualdehyde and hydrogen peroxide in photocatalytic oxygenation of p-xylene and reduction of oxygen with 9-mesityl-10-methylacridinium ion derivatives
  作者：Kei Ohkubo、Kentaro Mizushima、Ryosuke Iwata、Kazunori Souma、Nobuo Suzuki、Shunichi Fukuzumi

  DOI：10.1039/b920606j

  日期：——

  Photooxygenation of p-xylene by oxygen occurs efficiently under photoirradiation of 9-mesityl-2,7,10-trimethylacridinium ion (Me2Acr+–Mes) to yield p-tolualdehyde and hydrogen peroxide, which is initiated via photoinduced electron transfer of Me2Acr+–Mes to produce the electron-transfer state.

  在 9-甲巯基-2,7,10-三甲基吖啶离子（Me2Acr+-Mes）的光照射下，对二甲苯在氧气的作用下发生光氧化反应，生成对甲苯酚和过氧化氢，这种反应是通过 Me2Acr+-Mes 的光诱导电子转移产生电子转移态开始的。
• Synthesis of acridones through the ring expansion of isatins with arynes oxidated by O2 in air
  作者：Zerui Meng、Ran Zhao、Xiaowei Li、Chen Ma、Caixia Xie

  DOI：10.1016/j.tet.2022.133209

  日期：2023.1

  and environmental-friendly method for the construction of acridone derivatives with isatins and arynes was described. The isatins underwent a ring expansion process oxidized by O2 in the air and a broad scope of acridones in moderate to good yields were obtained. Baeyer-Villiger-type oxidation and intermolecular-nucleophilic addition were included, and no extra oxidant except O2 was needed.

  描述了一种用靛红和芳烃构建吖啶酮衍生物的简单且环保的方法。靛红经历了被空气中的 O 2氧化的扩环过程，并以中等至良好的产率获得了广泛的吖啶酮。包括Baeyer-Villiger型氧化和分子间亲核加成，除O 2外不需要额外的氧化剂。