12-methyl-7,12-dihydrobenzo[c]acridin-7-one | 50637-39-3

• 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: 12-methyl-7,12-dihydrobenzo[c]acridin-7-one
• 英文别名: 12-methylbenzo[c]acridin-7(12H)-one；N-methylbenz[c]acridin-7(12H)-one；12-methyl-12H-benzo[c]acridin-7-one；12-methylbenzo[c]acridin-7-one
• CAS: 50637-39-3
• 化学式: C₁₈H₁₃NO
• 分子量: 259.307
• InChiKey: LBWGTPVFXHRSNC-UHFFFAOYSA-N

物化性质

• 熔点：
  143-144 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  456.5±15.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(萘-1-氨基)-苯甲酸 在 lithium aluminium tetrahydride 、 碘苯二乙酸 、 sodium hydride 、 2-碘酰基苯甲酸 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 63.5h， 生成 12-methyl-7,12-dihydrobenzo[c]acridin-7-one
  参考文献：
  名称：

  PhI(OAc)₂-Mediated Intramolecular Oxidative Aryl-Aldehyde Csp²–Csp² Bond Formation: Metal-Free Synthesis of Acridone Derivatives

  摘要：

  A metal-free protocol for direct aryl-aldehyde Csp(2)-Csp(2) bond formation via a PhI(OAc)2-mediated intramolecular cross-dehydrogenative coupling (CDC) of various 2-(N-arylamino)aldehydes was developed. The novel methodology requires no need of preactivation of the aldehyde group, is applicable to a large variety of functionalized substrates, and most of all provides a convenient approach to the construction of biologically important acridone derivatives.

  DOI：

  10.1021/jo5011697

文献信息

• Synthesis of <i>o</i>-(Dimethylamino)aryl Ketones, Acridones, Acridinium Salts, and 1<i>H</i>-Indazoles by the Reaction of Hydrazones and Arynes
  作者：Anton V. Dubrovskiy、Richard C. Larock

  DOI：10.1021/jo302378w

  日期：2012.12.21

  A novel, efficient route to biologically and pharmaceutically important o-(dimethylamino)aryl ketones, acridones, acridinium salts, and 1H-indazoles has been developed starting from readily available hydrazones of aldehydes and o-(trimethylsilyl)aryl triflates. The reaction proceeds through arynes under mild conditions, tolerates a wide range of functional groups, and provides the final products in

  已经从容易获得的醛腙和邻（三甲基甲硅烷基）芳基三氟甲磺酸酯开始，开发了一种新的、有效的生物和药学上重要的邻（二甲基氨基）芳基酮、吖啶酮、吖啶盐和 1 H-吲唑的途径。该反应在温和条件下通过芳烃进行，可耐受范围广泛的官能团，并以良好至极好的收率提供最终产物。
• Carbanionic Friedel−Crafts Equivalents. Regioselective Directed <i>Ortho</i> and Remote Metalation−C−N Cross Coupling Routes to Acridones and Dibenzo[<i>b</i>,<i>f</i>]azepinones
  作者：Stephen L. MacNeil、Matthew Gray、Dmitry G. Gusev、Laura E. Briggs、Victor Snieckus

  DOI：10.1021/jo801856n

  日期：2008.12.19

  respectively, in good to excellent yields with regioselectivity which depends upon the presence or absence of directed metalation groups (DMGs). Brief investigations as follows are described: the synthesis of desmethyl acridone 15 (Scheme 4), an attempt to effect a double-directed remote metalation sequence which leads only to a monocyclization product 13 (Scheme 3), and an analogous but nonregioselective

  描述了通过碳负离子介导的对cri啶酮4（表2）和二苯并[b，f]氮杂环庚酮20（表4）的一般区域选择性途径。邻卤代苯甲酰胺1与苯胺2或16的Buchwald-Hartwig CN交叉偶联，然后简单的N-甲基化，可靠地提供了N-甲基二芳基胺3（表1）和18（表3）。用LDA处理后，3和18分别以良好或优异的产率转化为a烯4和二苯并[b，f]氮杂环庚酮20，其区域选择性取决于存在或不存在定向金属化基团（DMG）。描述了以下简要研究：合成去甲基a啶酮15（方案4），尝试实现双向远程金属化序列（仅导致单环化产物13）（方案3）以及类似但非区域选择性的途径黄酮22和二苯并[b，f]氧哌啶酮24（方案5）。DFT计算显示出化合物18b和23的低能构象，这说明了产物的形成，并表明环化反应处于动力学控制之下。
• Directed <i>ortho</i> and Remote Metalation - Cross Coupling Connections. Buchwald-Hartwig Synthesis of 2-Carbamoyl Diarylamines. Regioselective Anionic Routes to Acridones, Oxindoles, Dibenzo-[b,f]azepinones, and Anthranilate Esters
  作者：Stephen L. MacNeil、Matthew Gray、Laura E. Briggs、Jim J. Li、V. Snieckus

  DOI：10.1055/s-1998-1654

  日期：1998.4

  2-Carboxamido diarylamines 1f, 7, and 9, efficiently available by Buchwald-Hartwig C-N cross coupling reactions, serve as starting materials for new anionic routes to acridones 2d, oxindoles 10, dibenzo[b,f]azepinones 11, and anthranilate esters 8.

  2-甲酰胺基二芳基胺 1f、7 和 9 可通过布赫瓦尔德-哈特维格 C-N 交叉偶联反应有效地获得，可作为起始材料用于吖啶酮 2d、吲哚 10、二苯并[b,f]氮杂环庚酮 11 和蒽酸酯 8 的新阴离子路线。
• Sc(OTf)₃-Catalyzed Dehydrogenative Cyclization for Synthesis of <i>N</i>-Methylacridones
  作者：Xi-An Li、Hong-Li Wang、Shang-Dong Yang

  DOI：10.1021/ol400371h

  日期：2013.4.19

  A novel method has been developed for the synthesis of substituted N-methylacridones from 2-(N-methyl-N-phenylamino)benzaldehydes via dehydrogenative cyclization. This transformation involves two primary processes: the aldehyde first coordinates with Sc(OTf)(3) and induces the aromatic electrophilic substitution (SEAr) reaction to form the active intermediate N-methyl-acridin-9-ol, which is then quickly oxidized in situ to afford the acridones. Furthermore, the procedure involved is both environmental friendly and atom efficient; H2O is the only byproduct in this reaction.
• OPTICAL COMPENSATION SHEET, POLARIZING PLATE, AND LIQUID CRYSTAL DISPLAY DEVICE
  申请人：Kondou Shunichi

  公开号：US20090122233A1

  公开（公告）日：2009-05-14

  An optical compensation sheet having, on a transparent support, an optically anisotropic layer comprising a liquid crystalline compound fixed by using a photo-polymerization initiator system, wherein the photo-polymerization initiator system comprises at least one acylphosphine compound and at least one aromatic ketone compound selected from the group consisting of xanthene compounds, xanthone compounds, thioxanthone compounds and acridone compounds, which has less coloring and can be produced with less-power UV light, is provided.