(Z)-methyl 9-(4-ethoxy-4,5-dihydro-5,5-dimethyl-2-phenylpyrrol-3-ylidene)-9H-fluorene-2-carboxylate | 1164167-25-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (Z)-methyl 9-(4-ethoxy-4,5-dihydro-5,5-dimethyl-2-phenylpyrrol-3-ylidene)-9H-fluorene-2-carboxylate
• 英文别名: methyl (9Z)-9-(3-ethoxy-2,2-dimethyl-5-phenyl-3H-pyrrol-4-ylidene)fluorene-2-carboxylate
• CAS: 1164167-25-2
• 化学式: C₂₉H₂₇NO₃
• 分子量: 437.538
• InChiKey: NEPSCNAMMVLNAV-IZHYLOQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-methyl 9-(4-ethoxy-4,5-dihydro-5,5-dimethyl-2-phenylpyrrol-3-ylidene)-9H-fluorene-2-carboxylate 在 tetrafluoroboric acid 作用下， 以 乙醚 、 氘代氯仿 为溶剂， 以100%的产率得到
  参考文献：
  名称：

  Fluorenylidene−Pyrroline Biomimetic Light-Driven Molecular Switches

  摘要：

  A new family of biomimetic photoactivated molecular switches based in the retinal chromophore is described. Expedient synthesis allows a library of compounds with a different substitution pattern, including chiral substituents, to be obtained. The effect of substitution, solvent, and light source on the photoisomerization step has been assessed. The absorption maximum has been red-shifted ca. 50 nm with respect to related systems and rotation is now easily achieved by using visible light.

  DOI：

  10.1021/jo802792j
• 作为产物：
  描述：

  (E)-methyl 9-(4-ethoxy-4,5-dihydro-5,5-dimethyl-2-phenylpyrrol-3-ylidene)-9H-fluorene-2-carboxylate 以 乙腈 为溶剂， 生成 (Z)-methyl 9-(4-ethoxy-4,5-dihydro-5,5-dimethyl-2-phenylpyrrol-3-ylidene)-9H-fluorene-2-carboxylate
  参考文献：
  名称：

  Fluorenylidene−Pyrroline Biomimetic Light-Driven Molecular Switches

  摘要：

  A new family of biomimetic photoactivated molecular switches based in the retinal chromophore is described. Expedient synthesis allows a library of compounds with a different substitution pattern, including chiral substituents, to be obtained. The effect of substitution, solvent, and light source on the photoisomerization step has been assessed. The absorption maximum has been red-shifted ca. 50 nm with respect to related systems and rotation is now easily achieved by using visible light.

  DOI：

  10.1021/jo802792j

文献信息

• Photochemical characterization of biomimetic molecular switches
  作者：Laura Rivado-Casas、Marina Blanco-Lomas、Pedro J. Campos、Diego Sampedro

  DOI：10.1016/j.tet.2011.07.070

  日期：2011.9

  been studied. Both types of compounds share fast and controllable photoisomerization. Other competitive reaction pathways that could lead to low efficiency have been considered. Only weak fluorescence was measured and high photostability was found when irradiating these compounds for long times, together with high photoisomerization quantum yields. NAFPs are capable of using visible light, which could

  研究了芴基吡咯啉（FPs）和N-烷基化芴基吡咯啉（NAFPs）衍生物用作光驱动分子开关的性能。两种类型的化合物均具有快速且可控的光异构化作用。已经考虑了可能导致效率低下的其他竞争性反应途径。长时间照射这些化合物时，只能测到微弱的荧光，并且发现高的光稳定性，以及高的光异构化量子产率。NAFP能够使用可见光，这对于实际应用可能是有用的。
• Fluorenylidene−Pyrroline Biomimetic Light-Driven Molecular Switches
  作者：Laura Rivado-Casas、Diego Sampedro、Pedro J. Campos、Stefania Fusi、Vinicio Zanirato、Massimo Olivucci

  DOI：10.1021/jo802792j

  日期：2009.7.3

  A new family of biomimetic photoactivated molecular switches based in the retinal chromophore is described. Expedient synthesis allows a library of compounds with a different substitution pattern, including chiral substituents, to be obtained. The effect of substitution, solvent, and light source on the photoisomerization step has been assessed. The absorption maximum has been red-shifted ca. 50 nm with respect to related systems and rotation is now easily achieved by using visible light.