4-isopropyl-9-trimethylstannanylacridine | 602302-66-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-isopropyl-9-trimethylstannanylacridine
• 英文别名: 4-isopropyl-9-trimethylstannyl acridine；4-isopropyl-9-trimethylstannylacridine；4-isopropyl-9-trimethylstannanyl acridine；Trimethyl-(4-propan-2-ylacridin-9-yl)stannane
• CAS: 602302-66-9
• 化学式: C₁₉H₂₃NSn
• 分子量: 384.108
• InChiKey: CHTHCNRAZDVVKI-UHFFFAOYSA-N

物化性质

• 沸点：
  436.8±37.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  1,8-二溴萘 、 4-isopropyl-9-trimethylstannanylacridine 在 四(三苯基膦)钯 copper(II) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以5%的产率得到1,8-bis(4,4'-diisopropyl-9,9'-diacridyl)naphtalene
  参考文献：
  名称：

  Chiral 1,8-Diarylnaphthalenes, Methods of Making Them, and Their Use as Sensors

  摘要：

  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。

  公开号：

  US20070276140A1
• 作为产物：
  描述：

  三甲基氯化锡 、 9-bromo-4-isopropylacridine 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 以90%的产率得到4-isopropyl-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

文献信息

• Selective detection of Fe(III) ions in aqueous solution with a 1,8-diacridylnaphthalene-derived fluorosensor
  作者：Christian Wolf、Xuefeng Mei、Haala K. Rokadia

  DOI：10.1016/j.tetlet.2004.08.159

  日期：2004.10

  The syn-isomer of 1,8-bis(4,4'-diisopropyl-9,9'-diacridyl)naphthalene, 1, has been prepared by two consecutive Pd(PPh3)(4)-catalyzed Stille cross-coupling steps. This highly congested sensor undergoes Fe(III)-selective fluorescence quenching in water/acetonitrile even in the presence of excess of other metal ions. (C) 2004 Elsevier Ltd. All rights reserved.