(z)-3-(Anthracen-9-yl)acrylonitrile | 172098-31-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (z)-3-(Anthracen-9-yl)acrylonitrile
• 英文别名: (Z)-3-anthracen-9-ylprop-2-enenitrile
• CAS: 172098-31-6
• 化学式: C₁₇H₁₁N
• 分子量: 229.281
• InChiKey: ROBFRNVIZVJFKB-YHYXMXQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (z)-3-(Anthracen-9-yl)acrylonitrile 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 作用下， 生成 3-(9-anthryl)propylamine
  参考文献：
  名称：

  DNA小槽中蒽基探针对腺嘌呤-胸腺嘧啶碱基对的识别

  摘要：

  此处报道了几何异构体9（3-氨基丙基）蒽（APAC）和9（N-乙基）氨基甲基蒽（N-Et-AMAC）的合成和DNA结合特性。APAC的氨丙基侧链可以将氨基官能团定位在DNA凹槽中，以便与杂环碱基进行氢键键合。相反，N-Et-AMAC的N-乙基-氨基甲基侧链太短而无法在凹槽中接触。使用吸收，荧光，圆二色性（CD），单重态-单重态能量转移和DNA熔解实验检查DNA的结合特性。除了小牛胸腺DNA（CTDNA），我们还检查了poly（dA-dT），poly（dG-dC），poly（dA）-poly（dT）和poly（dI-dC）。光谱和热学研究表明蒽基探针插入到螺旋中。然而，结合特性取决于侧链以及DNA序列。APAC与poly（dA-dT）的结合比poly（dG-dC）的结合要好3.4倍，而N-Et-AMAC（APAC的几何异构体）的结合要好，与所检查的所有DNA聚合物几乎相同。通过使用肌苷-胞嘧

  DOI：

  10.1016/s0040-4020(00)00526-3
• 作为产物：
  描述：

  (E)-3-(anthracen-9-yl)acrylonitrile 以 苯 为溶剂， 反应 1.0h， 生成 (z)-3-(Anthracen-9-yl)acrylonitrile
  参考文献：
  名称：

  Wavelength Dependent Trans to Cis and Quantum Chain Isomerizations of Anthrylethylene Derivatives

  摘要：

  Anthrylethylene derivatives 1-4 were synthesized to study their photoisomerization. Interestingly 1 and 2 displayed wavelength dependent trans to cis photoisomerization, whose origin is due to preferential light absorption and excitation of the trans isomer. Triplet sensitization studies revealed that these anthrylethylenes undergo only cis to trans isomerization and not trans to cis isomerization. UV-vis absorption, fluorescence emission, and fluorescence quantum yields were determined for all anthrylethylenes. Dual fluorescence is observed for 1, 2, and cis-1, indicating two different emissive states. The fluorescence solvatochromism displayed by 1, 2, and cis-1 is a clear indication of the involvement of a charge transfer excited state. The quantum yield of isomerization was determined in various solvents and also as a function of concentration. We report here the first ''quantum chain isomerization'' that originates from a singlet excited state. The rationale put forward for the observed quantum chain isomerization process is the involvement of adiabatic isomerization from the singlet excited state and subsequent energy transfer to a ground state molecule.

  DOI：

  10.1021/jo00129a043

文献信息

• Adenine-Thymine Base Pair Recognition by an Anthryl Probe from the DNA Minor Groove
  作者：Challa V. Kumar、Emma H.A. Punzalan、Willy B. Tan

  DOI：10.1016/s0040-4020(00)00526-3

  日期：2000.9

  spectra of the probe-DNA complexes. The probes are achiral and binding to the helix leads to induced CD spectra in the 300–400 nm region, away from the DNA absorption bands. The positive CD bands observed indicate intercalation of the anthryl chromophore with its long axis perpendicular to the base-pair dyad axis. Fluorescence polarization data clearly support intercalation of both probes into the above

  此处报道了几何异构体9（3-氨基丙基）蒽（APAC）和9（N-乙基）氨基甲基蒽（N-Et-AMAC）的合成和DNA结合特性。APAC的氨丙基侧链可以将氨基官能团定位在DNA凹槽中，以便与杂环碱基进行氢键键合。相反，N-Et-AMAC的N-乙基-氨基甲基侧链太短而无法在凹槽中接触。使用吸收，荧光，圆二色性（CD），单重态-单重态能量转移和DNA熔解实验检查DNA的结合特性。除了小牛胸腺DNA（CTDNA），我们还检查了poly（dA-dT），poly（dG-dC），poly（dA）-poly（dT）和poly（dI-dC）。光谱和热学研究表明蒽基探针插入到螺旋中。然而，结合特性取决于侧链以及DNA序列。APAC与poly（dA-dT）的结合比poly（dG-dC）的结合要好3.4倍，而N-Et-AMAC（APAC的几何异构体）的结合要好，与所检查的所有DNA聚合物几乎相同。通过使用肌苷-胞嘧
• Wavelength Dependent Trans to Cis and Quantum Chain Isomerizations of Anthrylethylene Derivatives
  作者：V. Raj Gopal、A. Mahipal Reddy、V. Jayathirtha Rao

  DOI：10.1021/jo00129a043

  日期：1995.12

  Anthrylethylene derivatives 1-4 were synthesized to study their photoisomerization. Interestingly 1 and 2 displayed wavelength dependent trans to cis photoisomerization, whose origin is due to preferential light absorption and excitation of the trans isomer. Triplet sensitization studies revealed that these anthrylethylenes undergo only cis to trans isomerization and not trans to cis isomerization. UV-vis absorption, fluorescence emission, and fluorescence quantum yields were determined for all anthrylethylenes. Dual fluorescence is observed for 1, 2, and cis-1, indicating two different emissive states. The fluorescence solvatochromism displayed by 1, 2, and cis-1 is a clear indication of the involvement of a charge transfer excited state. The quantum yield of isomerization was determined in various solvents and also as a function of concentration. We report here the first ''quantum chain isomerization'' that originates from a singlet excited state. The rationale put forward for the observed quantum chain isomerization process is the involvement of adiabatic isomerization from the singlet excited state and subsequent energy transfer to a ground state molecule.