1-aza-9-methoxy-5,6,11,12-tetrahydrochrysene | 197297-04-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 1-aza-9-methoxy-5,6,11,12-tetrahydrochrysene
• 英文别名: 8-Methoxy-5,6,11,12-tetrahydronaphtho[1,2-h]quinoline
• CAS: 197297-04-4
• 化学式: C₁₈H₁₇NO
• 分子量: 263.339
• InChiKey: LWUUTZCBAKOILB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-aza-9-methoxy-5,6,11,12-tetrahydrochrysene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到1-aza-9-hydroxy-5,6,11,12-tetrahydrochrysene
  参考文献：
  名称：

  Synthesis and Spectroscopic Characterization of Two Azatetrahydrochrysenes as Potential Fluorescent Ligands for the Estrogen Receptor

  摘要：

  In an effort to improve upon the spectroscopic characteristics of donor-acceptor tetrahydrochrysene systems that we have previously prepared as fluorescent ligands for the estrogen receptor, we have synthesized two aza analogs as receptor ligand prototypes and characterized their absorbance and fluorescence spectra. 1-Aza-9-hydroxy-5,6,11,12-tetrahydrochrysene (4) and 1,3-diaza-9-hydroxy-5,6,11,12-tetrahydrochrysene (5) were prepared by convenient heterocyclization reactions on a known tricyclic ketone (6). The UV spectra of these heterocycles were quite insensitive to solvent polarity but showed marked red shifts under acidic or basic conditions. These heterocycles displayed complex fluorescence spectra, with emission bands around 400 nm in aprotic medium that shifted to longer wavelength in protic solvents. In many cases, acid and base caused strong red shifts in the emission, with large alterations in quantum yield; in some cases emission bands were shifted as far as 600 nm and dual-emission peaks were observed. Thus, these two azatetrahydrochrysenes show greater environmental sensitivity-especially to changes in pH-than do our previously described donor-acceptor tetrahydrochrysenes. The binding affinity of these ligand prototypes for the estrogen receptor, however, is low, indicating that other structure modifications will be required to make them useful fluorescent ligands for this receptor.

  DOI：

  10.1021/jo9708405
• 作为产物：
  描述：

  7-methoxy-3,4,9,10-tetrahydro-2H-phenanthren-1-one 在 N,N-二甲基丙烯基脲 、 溶剂黄146 、 lithium diisopropyl amide 作用下， 以 乙醇 为溶剂， 反应 34.0h， 生成 1-aza-9-methoxy-5,6,11,12-tetrahydrochrysene
  参考文献：
  名称：

  Synthesis and Spectroscopic Characterization of Two Azatetrahydrochrysenes as Potential Fluorescent Ligands for the Estrogen Receptor

  摘要：

  In an effort to improve upon the spectroscopic characteristics of donor-acceptor tetrahydrochrysene systems that we have previously prepared as fluorescent ligands for the estrogen receptor, we have synthesized two aza analogs as receptor ligand prototypes and characterized their absorbance and fluorescence spectra. 1-Aza-9-hydroxy-5,6,11,12-tetrahydrochrysene (4) and 1,3-diaza-9-hydroxy-5,6,11,12-tetrahydrochrysene (5) were prepared by convenient heterocyclization reactions on a known tricyclic ketone (6). The UV spectra of these heterocycles were quite insensitive to solvent polarity but showed marked red shifts under acidic or basic conditions. These heterocycles displayed complex fluorescence spectra, with emission bands around 400 nm in aprotic medium that shifted to longer wavelength in protic solvents. In many cases, acid and base caused strong red shifts in the emission, with large alterations in quantum yield; in some cases emission bands were shifted as far as 600 nm and dual-emission peaks were observed. Thus, these two azatetrahydrochrysenes show greater environmental sensitivity-especially to changes in pH-than do our previously described donor-acceptor tetrahydrochrysenes. The binding affinity of these ligand prototypes for the estrogen receptor, however, is low, indicating that other structure modifications will be required to make them useful fluorescent ligands for this receptor.

  DOI：

  10.1021/jo9708405

文献信息

• Synthesis and Spectroscopic Characterization of Two Azatetrahydrochrysenes as Potential Fluorescent Ligands for the Estrogen Receptor
  作者：Corinne Mazur Bowen、John A. Katzenellenbogen

  DOI：10.1021/jo9708405

  日期：1997.10.1

  In an effort to improve upon the spectroscopic characteristics of donor-acceptor tetrahydrochrysene systems that we have previously prepared as fluorescent ligands for the estrogen receptor, we have synthesized two aza analogs as receptor ligand prototypes and characterized their absorbance and fluorescence spectra. 1-Aza-9-hydroxy-5,6,11,12-tetrahydrochrysene (4) and 1,3-diaza-9-hydroxy-5,6,11,12-tetrahydrochrysene (5) were prepared by convenient heterocyclization reactions on a known tricyclic ketone (6). The UV spectra of these heterocycles were quite insensitive to solvent polarity but showed marked red shifts under acidic or basic conditions. These heterocycles displayed complex fluorescence spectra, with emission bands around 400 nm in aprotic medium that shifted to longer wavelength in protic solvents. In many cases, acid and base caused strong red shifts in the emission, with large alterations in quantum yield; in some cases emission bands were shifted as far as 600 nm and dual-emission peaks were observed. Thus, these two azatetrahydrochrysenes show greater environmental sensitivity-especially to changes in pH-than do our previously described donor-acceptor tetrahydrochrysenes. The binding affinity of these ligand prototypes for the estrogen receptor, however, is low, indicating that other structure modifications will be required to make them useful fluorescent ligands for this receptor.