2,4,7-tris(hydroxymethyl)-9,9-diethylfluorene | 859437-52-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2,4,7-tris(hydroxymethyl)-9,9-diethylfluorene
• 英文别名: [9,9-Diethyl-5,7-bis(hydroxymethyl)fluoren-2-yl]methanol
• CAS: 859437-52-8
• 化学式: C₂₀H₂₄O₃
• 分子量: 312.409
• InChiKey: CFCCBHMTPLZCHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4,7-tris(hydroxymethyl)-9,9-diethylfluorene 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以50%的产率得到9,9-diethylfluorene-2,4,7-tricarbaldehyde
  参考文献：
  名称：

  Synthesis of Two-Photon Absorbing Unsymmetrical Branched Chromophores through Direct Tris(bromomethylation) of Fluorene

  摘要：

  Branched fluorene-based chromophores bearing electron-donating diphenylamino or electron-withdrawing nitro groups were synthesized as well as their linear analogues. An efficient synthetic method was developed via a novel 2,4,7-tris(bromomethyl)-9,9-diethylfluorene intermediate. The bromomethyl groups in this key intermediate were converted to either phosphonate or carboxaldehyde moieties, facilitating preparation of a high functionality branched structure. It was found that the reactivity at position 4 is attenuated in the bromomethyl and phosphorylated derivates, facilitating the selective and systematic functionalization of the fluorenyl system. All compounds were stable up to ca. 350 degrees C, except for a sterically crowded branched derivative. The linear optical properties of the compounds were investigated by UV-visible, steady-state fluorescence, and excitation anisotropy spectroscopic measurements. Fluorescence quantum yields were greater than or equal to 0.84 for symmetric linear and unsymmetric branched derivatives. Very high two-photon absorption (2PA) cross-sections were achieved (5765 GM at 520 nm and 4194 GM at 570 nm), as determined with use of picosecond and femtosecond laser excitation sources, respectively.

  DOI：

  10.1021/jo0503512
• 作为产物：
  描述：

  2,4,7-tris(bromomethyl)-9,9-diethylfluorene 在 sodium tetrahydroborate 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 7.0h， 生成 2,4,7-tris(hydroxymethyl)-9,9-diethylfluorene
  参考文献：
  名称：

  带有卤代甲基的芴衍生物：晶体状态下的合成，分子结构和卤素/氢键模式

  摘要：

  介绍了在芳香族骨架的2、4和7位上带有卤代甲基的9,9-二乙基芴的合成，以及通过X射线衍射进行的分析。此外，还描述了有效的一步合成9,9-二乙基芴-2,4,7-三甲醛，提供比已知的三步反应顺序高三倍的甲醛产率。氯甲基和溴甲基取代的芴的晶体堆积主要通过Hal· ·· Hal和C–H ··· Hal接触来稳定，而碘取代的类似物的堆积则受三角形I 3合子C–H ·的影响。 ·· π和C-H ···我的相互作用。

  DOI：

  10.1002/ejoc.201801621

文献信息

• Fluorene Derivatives Bearing Halogenomethyl Groups: Synthesis, Molecular Structures, and Halogen/Hydrogen Bonding Patterns in the Crystalline State
  作者：Pierre Seidel、Anke Schwarzer、Monika Mazik

  DOI：10.1002/ejoc.201801621

  日期：2019.2.21

  The syntheses of 9,9‐diethylfluorenes bearing halogenomethyl groups in the 2, 4 and 7 positions of the aromatic skeleton, as well as their analyses by X‐ray diffraction are presented. In addition, the efficient one‐step synthesis of 9,9‐diethylfluorene‐2,4,7‐tricarbaldehyde, providing threefold higher yield of the carbaldehyde than the known three‐step reaction sequence, is also described. The crystal

  介绍了在芳香族骨架的2、4和7位上带有卤代甲基的9,9-二乙基芴的合成，以及通过X射线衍射进行的分析。此外，还描述了有效的一步合成9,9-二乙基芴-2,4,7-三甲醛，提供比已知的三步反应顺序高三倍的甲醛产率。氯甲基和溴甲基取代的芴的晶体堆积主要通过Hal· ·· Hal和C–H ··· Hal接触来稳定，而碘取代的类似物的堆积则受三角形I 3合子C–H ·的影响。 ·· π和C-H ···我的相互作用。
• Synthesis of Two-Photon Absorbing Unsymmetrical Branched Chromophores through Direct Tris(bromomethylation) of Fluorene
  作者：Sheng Yao、Kevin D. Belfield

  DOI：10.1021/jo0503512

  日期：2005.6.1

  Branched fluorene-based chromophores bearing electron-donating diphenylamino or electron-withdrawing nitro groups were synthesized as well as their linear analogues. An efficient synthetic method was developed via a novel 2,4,7-tris(bromomethyl)-9,9-diethylfluorene intermediate. The bromomethyl groups in this key intermediate were converted to either phosphonate or carboxaldehyde moieties, facilitating preparation of a high functionality branched structure. It was found that the reactivity at position 4 is attenuated in the bromomethyl and phosphorylated derivates, facilitating the selective and systematic functionalization of the fluorenyl system. All compounds were stable up to ca. 350 degrees C, except for a sterically crowded branched derivative. The linear optical properties of the compounds were investigated by UV-visible, steady-state fluorescence, and excitation anisotropy spectroscopic measurements. Fluorescence quantum yields were greater than or equal to 0.84 for symmetric linear and unsymmetric branched derivatives. Very high two-photon absorption (2PA) cross-sections were achieved (5765 GM at 520 nm and 4194 GM at 570 nm), as determined with use of picosecond and femtosecond laser excitation sources, respectively.