9-[(2-tert-butylphenoxy)carbonyl]-10-methylacridinium trifluoromethanesulfonate | 1065261-55-3

• 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: 9-[(2-tert-butylphenoxy)carbonyl]-10-methylacridinium trifluoromethanesulfonate
• 英文别名: 10-methyl-9-(2-tert-butylphenoxycarbonyl)-acridinium trifluoromethanesulfonate；9-(2-tert-Butylphenoxycarbonyl)-10-methylacridinium trifluoromethanesulfonate；(2-tert-butylphenyl) 10-methylacridin-10-ium-9-carboxylate;trifluoromethanesulfonate
• CAS: 1065261-55-3
• 化学式: CF₃O₃S*C₂₅H₂₄NO₂
• 分子量: 519.541
• InChiKey: MESJJSKLOILFOL-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  95.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  9-吖啶甲酰氯 在 4-二甲氨基吡啶 、 2,6-二叔丁基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 9-[(2-tert-butylphenoxy)carbonyl]-10-methylacridinium trifluoromethanesulfonate
  参考文献：
  名称：

  1H and 13C NMR spectra, structure and physicochemical features of phenyl acridine-9-carboxylates and 10-methyl-9-(phenoxycarbonyl)acridinium trifluoromethanesulphonates – alkyl substituted in the phenyl fragment

  摘要：

  The H-1 and C-13 NMR spectra of twelve phenyl acridine-9-carboxylates - alkyl-substituted in the phenyl fragment - and their 10-methyl-9-(phenoxycarbonyl)acridinium salts dissolved in CD3CN, CD3OD, CDCl3 and DMSO-d(6) were recorded in order to examine the influence of the structure of these compounds and the properties of the solvents on chemical shifts and H-1-H-1 coupling constants. Experimental data were compared with H-1 and C-13 chemical shifts predicted at the GIAO/DFT level of theory for DFT(B3LYP)/6-31G** optimised geometries of molecules, as well as with values of H-1 chemical shifts and H-1-H-1 coupling constants, estimated using ACD/HNMR database software to ensure that the assignment was correct. To investigate the relations between chemical shifts and selected structural or physicochemical characteristics of the target compounds, the values of several of these parameters were determined at the OFT or HE levels of theory. The HOMO and LUMO energies obtained at the HF level yielded the ionisation potentials and electron affinities of molecules. The DFT method provided atomic partial charges, dipole moments, LCAO coefficients of p(z) LUMO of selected C atoms, and angles reflecting characteristic structural features of the compounds. It was found that the experimentally determined H-1 and C-13 chemical shifts of certain atoms relate to the predicted dipole moments, the angles between the acridine and phenyl moieties, and the LCAO coefficients of the p(z) LUMO of the C atoms believed to participate in the initial step of the oxidation of the target compounds. The spectral and physicochemical characteristics of the target compounds were investigated in the context of their chemiluminogenic ability. (c) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2010.10.029

文献信息

• Spectral features of substituted 9-(phenoxycarbonyl)-acridines and their protonated and methylated cation derivatives
  作者：Karol Krzymiński、Alexander D. Roshal、Agnieszka Niziołek

  DOI：10.1016/j.saa.2007.10.045

  日期：2008.7

  The long-wavelength absorption of eight 9-(phenoxycarbonyl)-acridines and the 10-H-9-(phenoxycarbonyl)-acridinium and 10-methyl-9-(phenoxycarbonyl)-acridinium cations derived from them, substituted with an alkyl or trifluoroalkyl group at the benzene ring, occurs above 300 nm as the superposition of four bands. Three of these bands occupy comparable positions (expressed in nm) in all the compounds;

  从烷基或三氟烷基取代的8个9-（苯氧羰基）-ac啶和10-H-9-（苯氧羰基）-rid啶鎓和10-甲基-9-（苯氧羰基）-ac啶鎓阳离子的长波吸收苯环上的基团出现在300 nm以上，是四个谱带的重叠。在所有化合物中，这些带中的三个占据了相当的位置（以nm表示）。然而，第四种改变了位置，在中性分子中以低于400 nm的长波肩出现，但在阳离子中以高于400 nm的近乎独立的谱带出现。在长波长吸收带内激发产生的弱荧光相对于吸收发生红移，因此中性分子和阳离子的斯托克斯频移相似。斯托克斯位移倾向于随介质的定向极化率而增加。计算预测，长波长电子跃迁伴随着分子的结构变化。他们还表明，在这种跃迁之后，整个分子中的电子密度将发生大致均匀的变化，同时偶极矩也会发生细微变化，这说明了长波长区域的吸收较弱。预测的辐射失活速率常数和非辐射失活速率常数表明，在研究的分子中发生了有效的自旋-轨道耦合，这是荧光量子产率相
• Chemiluminogenic Features of 10-Methyl-9-(phenoxycarbonyl)acridinium Trifluoromethanesulfonates Alkyl Substituted at the Benzene Ring in Aqueous Media
  作者：Karol Krzymiński、Agnieszka Ożóg、Piotr Malecha、Alexander D. Roshal、Agnieszka Wróblewska、Beata Zadykowicz、Jerzy Błażejowski

  DOI：10.1021/jo1020882

  日期：2011.2.18

  electronically excited 10-methyl-9-acridinone, whose relaxation was accompanied by chemiluminescence (CL). The kinetic constants of CL decay, relative efficiencies of light emission, chemiluminescence quantum yields, and resistance toward alkaline hydrolysis were determined experimentally under various conditions. The mechanism of CL generation is considered on the basis of thermodynamic and kinetic parameters

  合成，纯化和鉴定了在苯环上带有烷基取代基的10-甲基-9-（苯氧羰基）ac基三氟甲烷磺酸盐。在与OOH的反应中-在碱性水性介质中，所研究化合物的阳离子被转化为电子激发的10-甲基-9-ac啶酮，其弛豫伴随着化学发光（CL）。在各种条件下，通过实验确定了CL衰减的动力学常数，相对发光效率，化学发光量子产率以及对碱水解的抵抗力。根据在DFT理论水平预测的反应步骤的热力学和动力学参数，考虑了CL生成的机理。化学发光效率是通过在OOH亲核取代之间C（9）的电中心的竞争的结果-或者OH -以及由此形成的中间体分解为电子激发的10-甲基-9-ac啶酮的能力。鉴定稳定的和中间的反应产物证实了建议的反应方案。获得的结果，尤其是“有用性”参数的依赖性（考虑了CL量子产率和水解的敏感性）对氧化过程中去除的实体腔体积的依赖，形成了合理设计化学发光的便捷框架10 -甲基-9-（苯氧羰基）ac阳离子。