9-hydroxy-8-methylphenalen-1-one | 78229-05-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 非那烯类
• 英文名称: 9-hydroxy-8-methylphenalen-1-one
• 英文别名: 2-methyl-9-hydroxyphenalen-1-one；2-methyl-9-hydroxyphenalenone；9-Hydroxy-2-methylphenalenone；MHPO；9-hydroxy-2-methyl-1-phenalenone
• CAS: 78229-05-7
• 化学式: C₁₄H₁₀O₂
• 分子量: 210.232
• InChiKey: DCPHXBGHQYFFEZ-UHFFFAOYSA-N

物化性质

• 熔点：
  127.8-129.1 °C(Solv: ethanol (64-17-5))
• 沸点：
  416.4±45.0 °C(Predicted)
• 密度：
  1.323±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  9-hydroxy-8-methylphenalen-1-one 、 异氰酸丙基三乙氧基硅烷 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以78%的产率得到(8-methyl-9-oxophenalen-1-yl) N-(3-triethoxysilylpropyl)carbamate
  参考文献：
  名称：

  Lanthanide‐Functionalized SBA‐15 Mesoporous Hybrids – Ultraviolet‐Visible Excitation and Visible–NIR Emission

  摘要：

  Abstract9‐Hydroxy‐2‐methyl‐phenalenone (MHPO) was synthesized and modified with 3‐(triethoxysilyl)propyl isocyanate (TEPIC) through a hydrogen atom addition reaction to achieve a new chemical linkage (named as MHPOSi). SBA‐15 mesoporous silica organically functionalized with MHPOSi was synthesized. The MHPOSi was linked to tetraethoxysilane (TEOS) through a condensation process in the presence of Pluronic P123 surfactant as a template. New Ln3+ (Eu3+, Nd3+, Yb3+) organic–inorganic mesoporous hybrid materials were prepared, in which the Ln3+ complexes are covalently attached to SBA‐15 and have 1,10‐phenanthroline (phen) as a second ligand. The resultant mesoporous hybrids were characterized by FTIR spectroscopy, small‐angle X‐ray diffraction, N2 adsorption–desorption measurements, thermal analysis, and UV/Vis spectroscopy. They all have high surface areas, uniform mesostructures, and good crystallinity. The photophysical properties of the functionalized mesoporous SBA‐15 networks are discussed in detail and they still present excitation capability in the visible region despite the modification of the organic silane. Subsequently, they exhibit characteristic visible (Eu3+) and near‐infrared (NIR) luminescence (Nd+ and Yb3+).

  DOI：

  10.1002/ejic.201300142
• 作为产物：
  描述：

  2-萘甲醚 在 aluminum (III) chloride 、 五氯化磷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.08h， 生成 9-hydroxy-8-methylphenalen-1-one
  参考文献：
  名称：

  Lanthanide‐Functionalized SBA‐15 Mesoporous Hybrids – Ultraviolet‐Visible Excitation and Visible–NIR Emission

  摘要：

  Abstract9‐Hydroxy‐2‐methyl‐phenalenone (MHPO) was synthesized and modified with 3‐(triethoxysilyl)propyl isocyanate (TEPIC) through a hydrogen atom addition reaction to achieve a new chemical linkage (named as MHPOSi). SBA‐15 mesoporous silica organically functionalized with MHPOSi was synthesized. The MHPOSi was linked to tetraethoxysilane (TEOS) through a condensation process in the presence of Pluronic P123 surfactant as a template. New Ln3+ (Eu3+, Nd3+, Yb3+) organic–inorganic mesoporous hybrid materials were prepared, in which the Ln3+ complexes are covalently attached to SBA‐15 and have 1,10‐phenanthroline (phen) as a second ligand. The resultant mesoporous hybrids were characterized by FTIR spectroscopy, small‐angle X‐ray diffraction, N2 adsorption–desorption measurements, thermal analysis, and UV/Vis spectroscopy. They all have high surface areas, uniform mesostructures, and good crystallinity. The photophysical properties of the functionalized mesoporous SBA‐15 networks are discussed in detail and they still present excitation capability in the visible region despite the modification of the organic silane. Subsequently, they exhibit characteristic visible (Eu3+) and near‐infrared (NIR) luminescence (Nd+ and Yb3+).

  DOI：

  10.1002/ejic.201300142

文献信息

• Fluorescent compounds for absorption and re-emission of radiation
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US05095099A1

  公开（公告）日：1992-03-10

  This invention concerns novel fluorescent compositions having the potential for absorption of visible and UV radiation and for re-emitting the radiation at longer wavelengths. The compositions comprise rare earth chelates containing a phenalenone nucleus.

  这项发明涉及具有吸收可见光和紫外线辐射潜力并在较长波长处重新发射辐射的新型荧光组合物。这些组合物包括含有苯并酮核的稀土螯合物。
• 2-Methyl- and 5-methyl-9-hydroxyphenalenone
  作者：R. C. Haddon、R. Rayford、A. M. Hirani

  DOI：10.1021/jo00335a060

  日期：1981.10
• Luminescent hybrid materials based on zeolite L crystals and lanthanide complexes: Host–guest assembly and ultraviolet–visible excitation
  作者：Lei Chen、Bing Yan

  DOI：10.1016/j.saa.2014.04.079

  日期：2014.10

  Several kinds of host-guest hybrid materials have been synthesized employing a ship in a bottle method by loading 9-hydroxy-2-methylphenalenone (MHPO) or 9-hydroxyphenalen (HPNP) from gas phase into the nanochannels of Ln(3+)-exchanged zeolite L (ZL) crystals (Ln=Gd or Eu). The resulting hybrids without lanthanide ions, MHPO-ZL, HPNP-ZL and the hybrids with lanthanide ions Ln-MHPO-ZL and Ln-HPNP-ZL are characterized with FT-IR, UV-vis DRS and photoluminescence spectroscopy. The photoluminescence properties of these hybrid materials have been analyzed and discussed, exhibiting the luminescence of Eu(3+) and ligands under the excitation at ultraviolet-visible region. These results provide useful data and can be expected to have potential application in the practical fields.
• HADDON, R. C.;RAYFORD, R.;HIRANI, A. M., J. ORG. CHEM., 1981, 46, N 22, 4587-4588
  作者：HADDON, R. C.、RAYFORD, R.、HIRANI, A. M.

  DOI：——

  日期：——
• US5095099A
  申请人：——

  公开号：US5095099A

  公开（公告）日：1992-03-10