9-(4-methylphenoxycarbonyl)-acridine | 158749-59-8

• 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-(4-methylphenoxycarbonyl)-acridine
• 英文别名: 4-methylphenyl acridine-9-carboxylate；(4-methylphenyl) acridine-9-carboxylate
• CAS: 158749-59-8
• 化学式: C₂₁H₁₅NO₂
• 分子量: 313.356
• InChiKey: HKIRIKCRHRCBLA-UHFFFAOYSA-N

物化性质

• 熔点：
  166-168 °C
• 沸点：
  505.4±23.0 °C(Predicted)
• 密度：
  1.250±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  9-(4-methylphenoxycarbonyl)-acridine 、 三氟甲烷磺酸甲酯 在 2,6-二叔丁基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成
  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
• 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 9-(4-methylphenoxycarbonyl)-acridine
  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

• Strongly Chemiluminescent Acridinium Esters under Neutral Conditions: Synthesis, Properties, Determination, and Theoretical Study
  作者：Manabu Nakazono、Yuji Oshikawa、Mizuho Nakamura、Hidehiro Kubota、Shinkoh Nanbu

  DOI：10.1021/acs.joc.6b02748

  日期：2017.3.3

  mechanism was composed of the nucleophilic addition reaction of hydroperoxide anion, dioxetanone ring formation, and nonadiabatic transition due to spin–orbit coupling around the transition state (TS) to the triplet state (T1) following the decomposition pathway. The TS which appeared in the thermal decomposition would be a rate-determining step for all three processes.

  合成了具有苯基和联苯基部分的各种新型a啶鎓酯衍生物，并研究了它们的最佳化学发光条件。发现了几种在中性条件下强烈化学发光的cri啶鎓酯，然后将这些衍生物用于检测过氧化氢和葡萄糖。具有强吸电子基团如氰基，甲氧羰基，和硝基在苯基部分的4-位上的苯基-10-甲基吖啶10λ酯4吖啶-9-羧酸盐三氟甲磺酸显示出强的化学发光强度。的化学发光强度3,4-二氰基苯基-10-甲基10λ 4吖啶-9-羧酸盐三氟甲磺酸较苯基-10-甲基10λ的强约100倍4在pH为7的过氧化氢和葡萄糖的线性校准范围吖啶-9-羧酸盐三氟甲磺酸使用0.05〜10 mM和10-2000μM3,4-（二甲氧基羰基）苯基-10-甲基10λ 4 -acridine- 9-羧酸盐三氟甲磺酸盐分别在pH 7和pH 7.5下。通过密度泛函理论的量子化学计算，评价了proposed啶鎓酯通过二氧杂环丁酮结构的化学发光反应机理。所提出的机理是由氢过氧
• 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
• Ultra-Sensitive Chemiluminescent Substrates for Enzymes and Their Conjugates
  申请人：Giri Pal Brij

  公开号：US20070225498A1

  公开（公告）日：2007-09-27

  New chemiluminescent compounds, stable in aqueous buffers, for use in biological assaying include acridanebased compounds and (1,2)-dioxetanes. Among the new acridanebased compounds are water-soluble acridanes, enhancer coupled acridanes, bis and trisacridanes as well as acridane-(1,2)-dioxetanes. Among the new (1,2)-dioxetanes are electron deficient group-containing dioxetanes and tethered bis-1,2-dioxetanes. The (1,2)-dioxetanes are useful as substrates for various enzymes. The acridanes can be admixed with an oxidizing agent. An aqueous buffer and, optionally, a stabilizer to form a substrate or reagent formulation useful for assaying, inter alia, HRP.

  新的化学发光化合物，稳定在水性缓冲液中，用于生物分析包括基于吖啶的化合物和(1,2)-二氧杂环辛烷。在新的基于吖啶的化合物中包括水溶性吖啶、增强剂偶联的吖啶、双吖啶和三吖啶以及吖啶-(1,2)-二氧杂环辛烷。在新的(1,2)-二氧杂环辛烷中包括含电子亏损基团的二氧杂环辛烷和连接的双-1,2-二氧杂环辛烷。这些(1,2)-二氧杂环辛烷可作为各种酶的底物。吖啶可以与氧化剂混合。水性缓冲液和可选的稳定剂可形成用于分析的底物或试剂配方，用于分析，包括HRP等。
• ULTRA-SENSITIVE CHEMILUMINESCENT SUBSTRATES FOR ENZYMES AND THEIR CONJUGATES
  申请人：Giri Brij Pal

  公开号：US20100317031A1

  公开（公告）日：2010-12-16

  New chemiluminescent compounds, stable in aqueous buffers, for use in biological assaying include acridane-based compounds and 1,2-dioxetanes. Among the new acridane-based compounds are water-soluble acridanes, enhancer coupled acridanes, bis and tris-acridanes as well as acridane-1,2-dioxetanes. Among the new 1,2-dioxetanes are electron deficient group-containing dioxetanes and tethered bis-1,2-dioxetanes. The 1,2-dioxetanes are useful as substrates for various enzymes. The acridanes can be admixed with an oxidizing agent an aqueous buffer and, optionally, a stabilizer to form a substrate or reagent formulation useful for assaying, inter alia, HRP.

  新的化学发光化合物，可以在水溶液缓冲液中稳定使用，用于生物测定，包括基于吖啶醚的化合物和1,2-二氧杂环烷。在新的基于吖啶醚的化合物中，包括水溶性吖啶醚、增强剂偶联的吖啶醚、双吖啶醚和三吖啶醚以及吖啶醚-1,2-二氧杂环烷。在新的1,2-二氧杂环烷中，包括含电子亏损基团的二氧杂环烷和连接的双1,2-二氧杂环烷。1,2-二氧杂环烷可用作各种酶的底物。吖啶醚可以与氧化剂混合在水溶液缓冲液中，并可选择性地加入稳定剂，形成用于测定HRP等的底物或试剂配方。
• NEW ULTRA-SENSITIVE CHEMILUMINESCENT SUBSTRATES FOR ENZYMES AND THEIR CONJUGATES
  申请人：Giri Brij Pal

  公开号：US20100317122A1

  公开（公告）日：2010-12-16

  New chemiluminescent compounds, stable in aqueous buffers, for use in biological assaying include acridane-based compounds and 1,2-dioxetanes. Among the new acridane-based compounds are water-soluble acridanes, enhancer coupled acridanes, bis and tris-acridanes as well as acridane-1,2-dioxetanes. Among the new 1,2-dioxetanes are electron deficient group-containing dioxetanes and tethered bis-1,2-dioxetanes. The 1,2-dioxetanes are useful as substrates for various enzymes. The acridanes can be admixed with an oxidizing agent. an aqueous buffer and, optionally, a stabilizer to form a substrate or reagent formulation useful for assaying, inter alia, HRP.5

  新的化学发光化合物，稳定在水缓冲液中，用于生物测定，包括基于蒽醌的化合物和1,2-二噁烷。新的基于蒽醌的化合物包括水溶性蒽醌，增强剂偶联蒽醌，双蒽醌和三蒽醌以及蒽醌-1,2-二噁烷。新的1,2-二噁烷包括含电子缺陷基团的二噁烷和拴接的双1,2-二噁烷。1,2-二噁烷可用作各种酶的底物。蒽醌可以与氧化剂混合。水缓冲液和可选的稳定剂，形成用于测定HRP等的底物或试剂配方。