9-bromo-4-methylacridine | 602302-56-7

• 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-4-methylacridine
• CAS: 602302-56-7
• 化学式: C₁₄H₁₀BrN
• 分子量: 272.144
• InChiKey: IMOYYCKDNQXEBQ-UHFFFAOYSA-N

物化性质

• 沸点：
  412.4±18.0 °C(Predicted)
• 密度：
  1.484±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  三甲基氯化锡 、 9-bromo-4-methylacridine 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 以84%的产率得到4-methyl-9-trimethylstannanylacridine
  参考文献：
  名称：

  Synthesis of Conformationally Stable 1,8-Diarylnaphthalenes:  Development of New Photoluminescent Sensors for Ion-Selective Recognition

  摘要：

  Highly constrained 1, 8-diarylnaphthalenes exhibiting stability to isomerization have been prepared utilizing two consecutive CuO-promoted Stille cross-couplings of 1,8-dibromonaphthalene and 4-alkyl-9trimethylstannylacridines. Screening of Pd catalysts Pd(PPh3)(4), PdCl(2)dppf, or Pd-2(dba)(3)/t-Bu3P and bases such as Cy2NMe, t-BuOK, K3PO4, and Cs2CO3 in DIME or DIMF revealed superior results of Stille over Suzuki coupling with acridylboronic acids or pinacolate derivatives. The meso syn- and C-2-symmetric anti-isomers of 1,8-bis(4,4'-dimethyl-9,9'-diacridyl)naphthalene, 2, and 1,8-bis(4,4'-diisopropyl-9,9'-diacridyl)naphthalene, 3, did not show any sign of syn/anti-interconversion after heating to 180 degreesC for 24 h. Using the Eyring equation, we calculated the Gibbs standard activation energy for isomerization, DeltaGdegrees(double dagger), to be higher than 180 kJ/mol. PM3 calculations of 2 and 3 suggest a highly congested structure exhibiting two parallel acridyl moieties perpendicular to the naphthalene ring. UV and fluorescence spectroscopy studies of 2 and 3 revealed remarkable quantum yields of these blue and green light emitters. Fluorescence titration experiments with the syn-isomer of 2 showed highly efficient quenching by Cu(II) ions, whereas almost no quenching effects were observed with Cu(l) and Zn(II) salts. The striking difference in fluorescence quenching was attributed to significant photoincluced electron transfer, resulting in nonradiative relaxation of excited Cu(II)-syn-2. Stern-Volmer plots of syn-2 in the presence Of CuCl2 showed a sigmoidal quenching curve indicating cooperative recognition, whereas a linear response was observed with CuCl and ZnCl2. Fluorescence experiments in the presence of various amounts of CuCl, CuBr, and Cu(ACN)(4)BF4 proved that the quenching is cation selective and independent of the nature of counteranions.

  DOI：

  10.1021/ja0358145
• 作为产物：
  描述：

  2-氯苯甲酸 在 copper(I) oxide 、 铜 、 potassium carbonate 、 三溴氧磷 作用下， 以 乙二醇甲醚 为溶剂， 反应 4.0h， 生成 9-bromo-4-methylacridine
  参考文献：
  名称：

  Synthesis of Conformationally Stable 1,8-Diarylnaphthalenes:  Development of New Photoluminescent Sensors for Ion-Selective Recognition

  摘要：

  Highly constrained 1, 8-diarylnaphthalenes exhibiting stability to isomerization have been prepared utilizing two consecutive CuO-promoted Stille cross-couplings of 1,8-dibromonaphthalene and 4-alkyl-9trimethylstannylacridines. Screening of Pd catalysts Pd(PPh3)(4), PdCl(2)dppf, or Pd-2(dba)(3)/t-Bu3P and bases such as Cy2NMe, t-BuOK, K3PO4, and Cs2CO3 in DIME or DIMF revealed superior results of Stille over Suzuki coupling with acridylboronic acids or pinacolate derivatives. The meso syn- and C-2-symmetric anti-isomers of 1,8-bis(4,4'-dimethyl-9,9'-diacridyl)naphthalene, 2, and 1,8-bis(4,4'-diisopropyl-9,9'-diacridyl)naphthalene, 3, did not show any sign of syn/anti-interconversion after heating to 180 degreesC for 24 h. Using the Eyring equation, we calculated the Gibbs standard activation energy for isomerization, DeltaGdegrees(double dagger), to be higher than 180 kJ/mol. PM3 calculations of 2 and 3 suggest a highly congested structure exhibiting two parallel acridyl moieties perpendicular to the naphthalene ring. UV and fluorescence spectroscopy studies of 2 and 3 revealed remarkable quantum yields of these blue and green light emitters. Fluorescence titration experiments with the syn-isomer of 2 showed highly efficient quenching by Cu(II) ions, whereas almost no quenching effects were observed with Cu(l) and Zn(II) salts. The striking difference in fluorescence quenching was attributed to significant photoincluced electron transfer, resulting in nonradiative relaxation of excited Cu(II)-syn-2. Stern-Volmer plots of syn-2 in the presence Of CuCl2 showed a sigmoidal quenching curve indicating cooperative recognition, whereas a linear response was observed with CuCl and ZnCl2. Fluorescence experiments in the presence of various amounts of CuCl, CuBr, and Cu(ACN)(4)BF4 proved that the quenching is cation selective and independent of the nature of counteranions.

  DOI：

  10.1021/ja0358145

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。
• 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。
• US7888509B2
  申请人：——

  公开号：US7888509B2

  公开（公告）日：2011-02-15
• [EN] CHIRAL 1,8-DIARYLNAPHTHALENES, METHODS OF MAKING THEM, AND THEIR USE AS SENSORS<br/>[FR] 1,8-DIARYLNAPHTALENES CHIRALES, PROCEDES D'ELABORATION, ET LEUR UTILISATION COMME CAPTEURS
  申请人：UNIV GEORGETOWN

  公开号：WO2005043124A2

  公开（公告）日：2005-05-12

  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.