2,5-dimethylphenyl acridine-9-carboxylate | 128649-37-6

• 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: 2,5-dimethylphenyl acridine-9-carboxylate
• 英文别名: (2,5-dimethylphenyl) acridine-9-carboxylate
• CAS: 128649-37-6
• 化学式: C₂₂H₁₇NO₂
• 分子量: 327.382
• InChiKey: XSOWTYRQEZMPRO-UHFFFAOYSA-N

物化性质

• 熔点：
  179-181 °C(Solv: cyclohexane (110-82-7))
• 沸点：
  546.0±38.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-dimethylphenyl acridine-9-carboxylate 、 三氟甲烷磺酸甲酯 以 二氯甲烷 为溶剂， 生成 9-(2,5-dimethylphenoxycarbonyl)-10-methylacridinium trifluoromethanesulfonate
  参考文献：
  名称：

  水性介质中苯环上取代的10-甲基-9-（苯氧羰基）ac基三氟甲磺酸烷基酯的化学发光特性

  摘要：

  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。

  DOI：

  10.1021/jo1020882
• 作为产物：
  描述：

  9-吖啶羧酸 在 吡啶 、 氯化亚砜 作用下， 反应 21.0h， 生成 2,5-dimethylphenyl acridine-9-carboxylate
  参考文献：
  名称：

  新型 9-取代 10-(ω-(琥珀酰亚胺氧羰基)烷基)吖啶酯的合成、结构解析和化学发光活性

  摘要：

  几种新的吖啶酯2 – 9的中心吖啶环带有 9-(2,5-二甲基苯氧羰基)、9-(2,6-双(三氟甲基)苯氧羰基)或 9-(2,6-二硝基苯氧羰基)基团，以及合成了 10-甲基、10-(3-(琥珀酰亚胺氧羰基)丙基)、10-(5-(琥珀酰亚胺氧羰基)戊基)或 10-(10-(琥珀酰亚胺氧羰基)癸基)基团，并测试了它们的化学发光特性. 当用碱性过氧化氢处理时，2,5-二甲基苯基吖啶酯会缓慢发光（发光），而 2,6-二硝基苯基和 2,6-双（三氟甲基）苯基酯会快速发光（闪光）。10位的取代基影响化合物的水解稳定性。

  DOI：

  10.1002/bio.4474

文献信息

• Acridinium compounds as chemiluminogenic label
  申请人：MOCHIDA PHARMACEUTICAL CO., LTD.

  公开号：EP0324202A1

  公开（公告）日：1989-07-19

  New acridinium compounds are provided which comply with formula 1, wherein A is a divalent organic moiety, such as an alkylene chain, X is a group which can be transformed together with C-9 of the acridine into a dioxetane by reaction with hydrogen peroxide, such as an aryloxy group, Y is a counter ion, and Z is a functional group, such as a carboxyl derivative. These acridinium compounds are useful as chemiluminogenic labels for both heterogeneous and homogeneous immunoassays.

  提供了符合式 1 的新吖啶鎓化合物，其中 A 是二价有机分子，如亚烷基链、 X 是可与吖啶的 C-9 一起通过与过氧化氢反应转化为二氧杂环丁烷的基团，如芳基、 Y 是反离子，以及 Z 是官能团，如羧基衍生物。 这些吖啶鎓化合物可用作化学发光标记，用于异质和均质免疫分析。
• 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
  作者：K. Krzymiński、P. Malecha、B. Zadykowicz、A. Wróblewska、J. Błażejowski

  DOI：10.1016/j.saa.2010.10.029

  日期：2011.1

  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.
• 2-Ethylphenyl acridine-9-carboxylate and 2,5-dimethylphenyl acridine-9-carboxylate
  作者：Artur Sikorski、Karol Krzymiński、Antoni Konitz、Jerzy Błażejowski

  DOI：10.1107/s0108270104030537

  日期：2005.1.15

  The title compounds, 2-ethylphenyl acridine-9-carboxylate, C22H17NO2, ( I), and 2,5-dimethylphenyl acridine-9-carboxylate, C22H17NO2, (II), form triclinic and monoclinic crystals, respectively. Related by a centre of symmetry, adjacent molecules of ( I) are linked in the lattice via a network of C - H ... pi and non-specific dispersive interactions. As a result, acridine moieties and independent phenyl moieties of ( I) are parallel in the lattice. The molecules of ( II), arranged in a 'head-to-tail' manner and related by a centre of symmetry, form pairs stabilized via C - H ... pi interactions. These are linked in the crystal via dispersive interactions. Acridine and independent phenyl moieties lie parallel within the pairs, while adjacent pairs are perpendicular, forming a herring-bone pattern.
• US5521103A
  申请人：——

  公开号：US5521103A

  公开（公告）日：1996-05-28
• US6018047A
  申请人：——

  公开号：US6018047A

  公开（公告）日：2000-01-25