2,6-二甲基苯基吖啶-9-羧酸酯 | 216668-66-5

• 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: 2,6-二甲基苯基吖啶-9-羧酸酯
• 英文名称: 2,6-dimethylphenyl acridine-9-carboxylate
• 英文别名: 2',6'-dimethylphenyl acridine-9-carboxylate；2,6-Dimethylphenyl 9-acridinecarboxylate；(2,6-dimethylphenyl) acridine-9-carboxylate
• CAS: 216668-66-5
• 化学式: C₂₂H₁₇NO₂
• 分子量: 327.382
• InChiKey: AOLUGQFBJPGMCK-UHFFFAOYSA-N

物化性质

• 熔点：
  162 °C
• 沸点：
  570.0±43.0 °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：

  2,6-二甲基苯基吖啶-9-羧酸酯 、 三氟甲烷磺酸甲酯 以 二氯甲烷 为溶剂， 生成 9-[(2,6-dimethylphenoxy)carbonyl]-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 4-二甲氨基吡啶 、 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2,6-二甲基苯基吖啶-9-羧酸酯
  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

文献信息

• Vitamin D derivatives with acyloxy groups in the side chains, process for their production, and the use for the production of pharmaceutical agents
  申请人：Schering AG

  公开号：US20030166622A1

  公开（公告）日：2003-09-04

  The invention relates to vitamin D derivatives of general formula I, 1 process for production, and the use for the production of pharmaceutical agents.

  本发明涉及一般式I的维生素D衍生物，1种生产方法以及用于制药剂的生产的用途。
• Hydrophilic chemilumescent acridinium labeling reagents
  申请人：Quest Diagnostic Investments Incorporated

  公开号：US20040038294A1

  公开（公告）日：2004-02-26

  In accordance with the present invention, it has been discovered that introduction of hydrophilic sulfoalkyl substituents and/or hydrophilic linkers derived from homocysteic acid, cysteic acid, glycine peptides, tetraethylene oxide, and the like, offset the hydrophobicity of the acridinium ring system to produce a more soluble label which can be attached to an antibody at higher loading before precipitation and aggregation problems are encountered. Additional compounds described herein contain linkers derived from short peptides and tetraethylene oxide which increase aqueous solubility due to hydrogen bonding with water molecules. The present invention also embraces reagents for multiple acridinium labeling for signal amplification composed of a peptide bearing several acridinium esters with sulfonate groups at regularly spaced intervals for increased solubility. The invention also embraces assays employing the above-described compounds.

  根据本发明，人们发现引入亲水性磺烷基取代基和/或亲水性连接体（来源于高半胱氨酸、半胱氨酸、甘氨酸肽、四亚甲基环氧乙烷等），可以抵消吖啶环系统的疏水性，从而产生一种可溶性更强的标签，在遇到沉淀和聚集问题之前，这种标签可以更高的负载量连接到抗体上。本发明中描述的其他化合物含有源自短肽和四氧化乙烯的连接体，由于与水分子的氢键作用，这些连接体增加了水溶性。本发明还包括用于信号放大的多重吖啶鎓标记试剂，该试剂由含有多个吖啶鎓酯的肽组成，肽与磺酸基之间有规律的间隔，以增加溶解度。本发明还包括采用上述化合物的检测方法。
• 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.
• MEASUREMENT OF HYDRIDE USING CHEMILUMINESCENT ACRIDINIUM COMPOUNDS
  申请人：BAYER CORPORATION

  公开号：EP1049933B1

  公开（公告）日：2005-09-14
• EP1539702A4
  申请人：——

  公开号：EP1539702A4

  公开（公告）日：2005-09-07