9-bromo-3-(3',5'-dimethylphenyl)acridine | 783325-77-9

• 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-bromo-3-(3',5'-dimethylphenyl)acridine
• 英文别名: 3-(3,5-dimethylphenyl)-9-bromoacridine；9-bromo-3-(3,5-dimethylphenyl)acridine
• CAS: 783325-77-9
• 化学式: C₂₁H₁₆BrN
• 分子量: 362.269
• InChiKey: LUFBELDZRXRPFJ-UHFFFAOYSA-N

物化性质

• 沸点：
  500.5±40.0 °C(Predicted)
• 密度：
  1.367±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-bromo-3-(3',5'-dimethylphenyl)acridine 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以91%的产率得到9-bromo-3-(3,5-dimethylphenyl)acridine N-oxide
  参考文献：
  名称：

  Highly Congested Nondistorted Diheteroarylnaphthalenes:  Model Compounds for the Investigation of Intramolecular π-Stacking Interactions

  摘要：

  The rigid, highly congested structure of 1,8-diacridylnaphthalenes has been studied in solution and in the solid state. The unique geometry of these compounds forces the acridyl rings to undergo face-to-face interactions while rendering T-shaped orientations and face-to-edge interactions impossible. Crystallographic analysis shows that splaying between the heteroaryl rings decreases while twisting between the cofacial rings increases as the acridyl nitrogens of the 1,8-diacridyl-naphthalene framework are subsequently oxidized. The peri-acridyl rings are slightly splayed but remain perfectly planar in all cases. The significant decrease in splaying indicates enhanced pi-pi-attraction between the electron-rich acridyl N-oxide moieties, which is in agreement with recently reported symmetry-adapted perturbation theory calculations. The T-stacking and the molecular geometry between the acridyl rings observed in the solid state have been confirmed through in-solution studies showing characteristic proton NMR upfield shifts and optical properties indicative of static intramolecular arene-arene interactions. Acridyl protons located directly above the adjacent aryl moiety as a consequence of twisting between the heteroaryl rings were identified by COSY NMR measurements and found to intrude into the pi-cloud and diamagnetic ring current of the neighboring acridine. Different shapes and strong red shifts of the fluorescence emission maxima of the diacridylnaphthalenes in comparison to parental acridyl monomers have been attributed to static excimer emission.

  DOI：

  10.1021/jo0479361
• 作为产物：
  描述：

  4-溴-2-氯苯甲酸 在 四(三苯基膦)钯 、 铜 copper(I) oxide 、 乙二醇乙醚 、 四丁基溴化铵 、 sodium carbonate 、 potassium carbonate 、 三溴氧磷 作用下， 以 水 为溶剂， 反应 26.33h， 生成 9-bromo-3-(3',5'-dimethylphenyl)acridine
  参考文献：
  名称：

  通过使用手性钪络合物的竞争结合测定法测定未保护氨基酸、胺、氨基醇和羧酸的对映体过量和浓度

  摘要：

  开发了一种实用的紫外-可见光传感方法，用于对水溶液中未受保护的氨基酸、胺、氨基醇和羧酸进行对映选择性微量分析。使用衍生自 1,8-双(3-(3',5'-二甲基苯基)-9-的钪复合物，通过两种简单的竞争性结合测定，可以高精度测定各种手性底物的浓度和对映体组成。吖啶基)萘N,N'-二氧化物。

  DOI：

  10.1021/ja0636486

文献信息

• Chiral 1,8-Diarylnaphthalenes, Methods of Making Them, and Their Use as Sensors
  申请人：Wolf Christian

  公开号：US20070276140A1

  公开（公告）日：2007-11-29

  One aspect of the invention relates to 1,8-diarylnaphthalene compounds. In certain embodiments, a compound of the invention is an N-oxide of a 1,8-diarylnaphthalene. In certain embodiments, the aryl group is an optionally substituted acridyl group. In certain embodiments, a compound of the invention is a single steroisomer. In certain embodiments, a compound of the invention is a single enantiomer. Another aspect of the present invention relates to a method of detecting the presence of an analyte in a sample by monitoring the fluorescence of a compound of the invention in a sample. In certain embodiments, the analyte is a metal ion. Another aspect of the present invention relates to a method of determining the enantiomeric purity of an analyte by monitoring the fluorescence of a compound of the invention in the presence of the analyte. In certain embodiments, the analyte is a compound that is capable of hydrogen bonding.

  该发明的一个方面涉及1,8-二芳基萘化合物。在某些实施例中，该发明的化合物是1,8-二芳基萘的N-氧化物。在某些实施例中，芳基是一个可选择取代的吖啶基。在某些实施例中，该发明的化合物是一个单对映体。在某些实施例中，该发明的化合物是一个单对映异构体。本发明的另一个方面涉及通过监测样品中该发明的化合物的荧光来检测样品中存在的分析物的方法。在某些实施例中，分析物是金属离子。本发明的另一个方面涉及通过在分析物存在的情况下监测该发明的化合物的荧光来确定分析物的对映体纯度的方法。在某些实施例中，分析物是能够进行氢键结合的化合物。
• Synthesis of a Sterically Crowded Atropisomeric 1,8-Diacridylnaphthalene for Dual-Mode Enantioselective Fluorosensing
  作者：Xuefeng Mei、Rhia M. Martin、Christian Wolf

  DOI：10.1021/jo0600353

  日期：2006.3.31

  Stille cross-coupling steps using tetrakis(triphenylphosphine)palladium(0) as catalyst in the presence of copper(II) oxide. The preparation of 1 involved formation of 4-(3‘,5‘-dimethylphenyl)-2-chlorobenzoic acid, 7, through microwave-assisted Suzuki coupling of 4-bromo-2-chlorobenzoic acid, 10, and 3,5-dimethylphenylboronic acid, 11, followed by regioselective amination with aniline and acridine ring

  已开发出一种有效的合成路线，可用于空间拥挤的1,8-二杂芳基萘衍生的对映选择性荧光传感器，该传感器在两种不同的检测模式下利用荧光寿命和强度进行操作。钯催化的Negishi，Kumada，Suzuki，Hiyama和Stille偶联方法的筛选显示，后者以较高的收率提供了高度拥挤的1,8-二芳基萘。尽管存在严重的空间位阻，但从1,8-二溴萘，14和3以68％的收率获得了轴向手性1,8-双（3-（3'，5'-二甲基苯基）-9--啶基）萘1 -（3'，5'-二甲基苯基）-9-三丁基苯乙烯内酰胺，13通过在氧化铜（II）存在下使用四（三苯基膦）钯（0）​​作为催化剂的两个连续的Stille交叉偶联步骤。1的制备涉及通过4-溴-2-氯苯甲酸，10和3,5-二甲基苯硼酸的微波辅助Suzuki偶联形成4-（3'，5'-二甲基苯基）-2-氯苯甲酸7酸11，然后在氧溴化磷中用苯胺和a啶环结构进行区域选择性胺化
• Chiral 1,8-diarylnaphthalenes, methods of making them, and their use as sensors
  申请人：Georgetown University

  公开号：US07888509B2

  公开（公告）日：2011-02-15

  One aspect of the invention relates to 1,8-diarylnaphthalene compounds. In certain embodiments, a compound of the invention is an N-oxide of a 1,8-diarylnaphthalene. In certain embodiments, the aryl group is an optionally substituted acridyl group. In certain embodiments, a compound of the invention is a single steroisomer. In certain embodiments, a compound of the invention is a single enantiomer. Another aspect of the present invention relates to a method of detecting the presence of an analyte in a sample by monitoring the fluorescence of a compound of the invention in a sample. In certain embodiments, the analyte is a metal ion. Another aspect of the present invention relates to a method of determining the enantiomeric purity of an analyte by monitoring the fluorescence of a compound of the invention in the presence of the analyte. In certain embodiments, the analyte is a compound that is capable of hydrogen bonding.

  本发明的一个方面涉及1,8-二芳基萘化合物。在某些实施方式中，本发明的化合物是1,8-二芳基萘的N-氧化物。在某些实施方式中，芳基基团是可选取代的吖啶基团。在某些实施方式中，本发明的化合物是单一立体异构体。在某些实施方式中，本发明的化合物是单一对映体。本发明的另一个方面涉及通过监测样品中本发明化合物的荧光来检测样品中分析物的存在的方法。在某些实施方式中，分析物是金属离子。本发明的另一个方面涉及通过在分析物存在的情况下监测本发明化合物的荧光来确定分析物的对映体纯度的方法。在某些实施方式中，分析物是能够进行氢键作用的化合物。
• Enantioselective Sensing of Chiral Carboxylic Acids
  作者：Xuefeng Mei、Christian Wolf

  DOI：10.1021/ja0459781

  日期：2004.11.1

  A chiral 1,8-diacridylnaphthalene-derived fluorosensor has been prepared and used for enantioselective sensing of a broad variety of chiral carboxylic acids including amino acids, aliphatic acids, arylalkanoic acids, and halogenated carboxylic acids. Fluorescence titration experiments in acetonitrile gave linear Stern-Volmer plots for 1:1 and 1:2 complexes and enantioselectivities up to 4.5.
• Determination of enantiomeric excess and concentration of chiral compounds using a 1,8-diheteroarylnaphthalene-derived fluorosensor
  作者：Xuefeng Mei、Christian Wolf

  DOI：10.1016/j.tetlet.2006.09.012

  日期：2006.11

  Enantioselective fluorosensing using a rigid C-2-symmetric 1,8-diacridylnaphthalene N,N'-dioxide sensor allows accurate determination of both the enantiomeric composition and concentration of several analytes capable of chiral hydrogen bonding. (c) 2006 Elsevier Ltd. All rights reserved.