12-甲基苯并[a]吖啶 | 3340-93-0

• 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
• 中文名称: 12-甲基苯并[a]吖啶
• 英文名称: 9-methylbenz[a]acridine
• 英文别名: 9-Methyl-1,2-benzacridin；12-methylbenzacridine；12-methylbenzo[a]acridine；12-Methylbenz(a)acridine
• CAS: 3340-93-0
• 化学式: C₁₈H₁₃N
• 分子量: 243.308
• InChiKey: IIPYOAZDUATCMJ-UHFFFAOYSA-N

物化性质

• 熔点：
  144.5°C
• 沸点：
  376.18°C (rough estimate)
• 密度：
  0.8933 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 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：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

SDS

反应信息

• 作为反应物：
  描述：

  12-甲基苯并[a]吖啶 以 乙腈 为溶剂， 反应 4.0h， 生成 1,1,2,2-四苯基乙烷
  参考文献：
  名称：

  Absolute Asymmetric Photoreactions of Acridines with Diphenylacetic Acid in their Cocrystals

  摘要：

  Solid-state photodecarboxylation occurs in a chiral cocrystal of acridine and diphenylacetic acid to afford a chiral condensation product in modest enantiomeric excess. A chiral cocrystal of 9-methylbenz[c]acridine and diphenylacetic acid also undergoes similar photodecarboxylation but gives an almost racemic product. The different enantioselectivities between the two chiral cocrystals can be understood on the basis of the molecular arrangements in the lattice.

  DOI：

  10.1080/15421400590958520
• 作为产物：
  描述：

  1-乙酰基-2-萘酚 在 硫酸 、 碘 、 溶剂黄146 作用下， 生成 12-甲基苯并[a]吖啶
  参考文献：
  名称：

  Buu-Hoi et al., Journal of the Chemical Society, 1955, p. 1082

  摘要：

  DOI：

文献信息

• <i>tert</i>-Butyl Bromide-Promoted Intramolecular Cyclization of 2-Arylamino Phenyl Ketones and Its Combination with Cu-Catalyzed C–N Coupling: Synthesis of Acridines at Room Temperature
  作者：Zifeng Cao、Yuan Zhu、Xiaoman Li、Yang He、Jinli Zhang、Liang Xu、Yu Wei

  DOI：10.1021/acs.joc.0c00137

  日期：2020.8.7

  2-arylamino phenyl ketones is established to supersede the traditional high-temperature, strongly acidic conditions and achieve 9-substituted acridines, by virtue of the combination of 2,2,2-trifluoroethanol and tert-butyl bromide. This protocol can be merged well with the preceding Cu-catalyzed intermolecular Chan–Evans–Lam cross-coupling reactions, therefore enabling pot-economic modular synthesis of 9-substituted

  在此，借助于2,2,2-三氟乙醇和叔丁基溴的组合，建立了2-芳基氨基苯基酮的分子内环化体系，以取代传统的高温，强酸性条件并获得9-取代的a啶。。该方案可以与之前的铜催化的分子间Chan–Evans–Lam交叉偶联反应很好地合并，因此可以在室温下从容易获得的2-氨基苯基酮和芳基硼酸进行锅内经济的模块化合成9-取代的cr啶。
• Benzo[a]acridinylmethyl esters as pH sensitive fluorescent photoactive precursors: synthesis, photophysical, photochemical and biological applications
  作者：Mohammed Ikbal、Biswajit Saha、Shrabani Barman、Sanghamitra Atta、Deb Ranjan Banerjee、Sudip Kumar Ghosh、N. D. Pradeep Singh

  DOI：10.1039/c3ob42600a

  日期：——

  A newsworthy class of carboxylate esters based on the (benzo[a]acridin-12-yl)methyl (BAM) chromophore has been shown to perform dual functions as a “pH sensitive fluorescent probe” and a “phototrigger” for acids. The photophysical properties of all the BAM ester conjugates were investigated and found to be highly sensitive to solvent polarity, H-bonding capability and pH of the environment. On irradiation using UV light (≥410 nm), BAM ester conjugates underwent heterolytic cleavage of C–O bonds resulting in efficient release of carboxylic and amino acids. Interestingly, the newly synthesized BAM chromophore was also explored for the construction of a drug delivery system (DDS). In the current DDS, the BAM chromophore plays two important roles: (i) a “fluorophore” for cell imaging and (ii) a “phototrigger” for the drug release. In vitro biological studies revealed that the newly developed BAM based DDS has a good biocompatibility, cellular uptake properties and efficient photoregulated anticancer drug release ability.

  一种基于（苯并[a]吖啶-12-基）甲基（BAM）发色团的羧酸酯类具有双重功能，既是 "pH 值敏感荧光探针"，又是酸的 "光触发器"。研究发现，所有 BAM 酯共轭物的光物理特性对溶剂极性、H 键能力和环境的 pH 值高度敏感。在紫外线（≥410 纳米）的照射下，BAM 酯共轭物的 C-O 键发生异溶解裂解，从而有效释放出羧酸和氨基酸。有趣的是，新合成的 BAM 发色团还被用于构建给药系统（DDS）。在目前的 DDS 中，BAM 发色团扮演着两个重要角色：(i) 细胞成像的 "荧光团"；(ii) 药物释放的 "光触发器"。体外生物学研究表明，新开发的基于 BAM 的 DDS 具有良好的生物相容性、细胞吸收特性和高效的光调节抗癌药物释放能力。
• Synthesis and carcinogenic activity of oxidized benzacridines: potential metabolites of the strong carcinogen 7-methylbenz[c]acridine and of the inactive isomer 12-methylbenz[a]acridine
  作者：Martine Croisy-Delcey、Alain Croisy、Francois Zajdela、Jean Marc Lhoste

  DOI：10.1021/jm00356a038

  日期：1983.2

  The synthesis of 15 compounds related either to the benz[c]acridine or to the benz[a]acridine series is reported. Spectral data, i.e., NMR and EI fragmentation, are given. These compounds were tested for carcinogenic activity in mice of the XVIInc/Z strain by subcutaneous injection. Only three weak carcinogens were detected, 5,6-dihydro-5,6-dihydroxy-12-methylbenz[a]acridine, 3-methoxy-7-methylbenz[c]acridine

  报道了与苯并[c] ac啶或与苯并[a] ac啶系列有关的15种化合物的合成。给出了光谱数据，即NMR和EI碎片。通过皮下注射测试了这些化合物在XVIInc / Z株小鼠中的致癌活性。仅检测到三种弱致癌物：5,6-二氢-5,6-二羟基-12-甲基苯并[a] ac啶，3-甲氧基-7-甲基苯并[c] ac啶和4-乙酰氧基-7-甲基苯并[c]啶。考虑到先前使用其他苯甲cr啶和缩合喹啉获得的数据，讨论了这些结果。
• Rapid Synthesis of Acridines Using Microwave
  作者：Hideko Koshima、Kosuke Kutsunai

  DOI：10.3987/com-02-9493

  日期：——

  Microwave irradiation for several minutes caused reaction of diarylamines with carboxylic acids in the presence of zinc chloride to give 9-substituted acridines in good yield.
• Michailow; Ter-Sarkisjan, Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1954, p. 656,661;engl.Ausg. S.559,561
  作者：Michailow、Ter-Sarkisjan

  DOI：——

  日期：——