3-(11-hydroxy-undecyloxy)-benzaldehyde | 320722-43-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-(11-hydroxy-undecyloxy)-benzaldehyde
• 英文别名: 3-(11-hydroxyundecanyloxy)benzaldehyde；3-[(11-Hydroxyundecyl)oxy]benzaldehyde；3-(11-hydroxyundecoxy)benzaldehyde
• CAS: 320722-43-8
• 化学式: C₁₈H₂₈O₃
• 分子量: 292.419
• InChiKey: PVKOOSNGUMXKFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  21.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(11-hydroxy-undecyloxy)-benzaldehyde 在 三乙胺 、 PEG 400 作用下， 以 二氯甲烷 为溶剂， 反应 23.25h， 生成 3-(11-thioacetyl-undecyloxy)-benzaldehyde
  参考文献：
  名称：

  Disulfide-Strapped Porphyrins for Monolayer Formation on Gold

  摘要：

  [GRAPHICS]Porphyrins with a disulfide-containing strap have been prepared as an alternative to dithiols for self-assembled monolayer formation on gold surfaces. The strapped porphyrins have the advantage of greater air stability than their dithiol analogues. Cis and trans atropisomers of a strapped porphyrin were isolated. Gold electrodes modified with dithiol and disulfide porphyrins were not identical as evidenced by contact angle or electrochemical measurements.

  DOI：

  10.1021/ol006615i
• 作为产物：
  描述：

  11-溴-1-十一醇 、 间羟基苯甲醛 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以89%的产率得到3-(11-hydroxy-undecyloxy)-benzaldehyde
  参考文献：
  名称：

  Synthesis of Porphyrin–CdSe Quantum Dot Assemblies: Controlling Ligand Binding by Substituent Effects

  摘要：

  Cadmium selenide quantum dots of 2.2-2.3 nm diameter were prepared by phosphorus-free methods using oleic acid as stabilizing surface ligand. Ligand exchange monitored quantitatively by H-1 NMR. spectroscopy gave an estimate of 30-38 monodentate ligands per nanocrystal, with a ligand density of 1.8-2.3 nm(-2). The extent of ligand exchange with macrocycles carrying one or more functional groups was investigated, with the aim of producing nanocrystal-macrocycle conjugates With a limited number of coligands. Metal-free porphyrins are able to sequester the Cd2+ ions, from the Cd(oleate)(2) outer layer of the nanocrystals. Zinc porphyrin complexes carrying one carboxylate function displace oleate efficiently to give porphyrin/CdSe composites with porphyrins stacked upright on the crystal surface. Porphyrins with four potential ligating sites are able to bind to the crystal surface only if the donors are at the end of sufficiently long and flexible tethers. High-dilution methods allowed the synthesis and isolation of well-defined composites of composition [CdSe{porphyrin}(2)], where porphyrin 5,10,15,20-tetrakis{3-(carboxy-n-alkyloxy)phenyl}porphyrinato zinc (n = 5 or 10) and 5,10,15,20-tetrakis{3-(11-undecenyloxythiol)phenyl}porphyrinato zinc. Comparison of the composition data obtained by H-1 NMR spectroscopy with luminescence quenching behavior suggests a dependence of quenching efficiency On the tether length. Luminescence quenching was also observed for porphyrins that, according to H-1 NMR results, do not undergo surface ligand exchange.

  DOI：

  10.1021/acs.inorgchem.5b00892

文献信息

• Disulfide-Strapped Porphyrins for Monolayer Formation on Gold
  作者：James E. Redman、Jeremy K. M. Sanders

  DOI：10.1021/ol006615i

  日期：2000.12.1

  [GRAPHICS]Porphyrins with a disulfide-containing strap have been prepared as an alternative to dithiols for self-assembled monolayer formation on gold surfaces. The strapped porphyrins have the advantage of greater air stability than their dithiol analogues. Cis and trans atropisomers of a strapped porphyrin were isolated. Gold electrodes modified with dithiol and disulfide porphyrins were not identical as evidenced by contact angle or electrochemical measurements.
• Synthesis of Porphyrin–CdSe Quantum Dot Assemblies: Controlling Ligand Binding by Substituent Effects
  作者：Isabelle Chambrier、Chiranjib Banerjee、Sonia Remiro-Buenamañana、Yimin Chao、Andrew N. Cammidge、Manfred Bochmann

  DOI：10.1021/acs.inorgchem.5b00892

  日期：2015.8.3

  Cadmium selenide quantum dots of 2.2-2.3 nm diameter were prepared by phosphorus-free methods using oleic acid as stabilizing surface ligand. Ligand exchange monitored quantitatively by H-1 NMR. spectroscopy gave an estimate of 30-38 monodentate ligands per nanocrystal, with a ligand density of 1.8-2.3 nm(-2). The extent of ligand exchange with macrocycles carrying one or more functional groups was investigated, with the aim of producing nanocrystal-macrocycle conjugates With a limited number of coligands. Metal-free porphyrins are able to sequester the Cd2+ ions, from the Cd(oleate)(2) outer layer of the nanocrystals. Zinc porphyrin complexes carrying one carboxylate function displace oleate efficiently to give porphyrin/CdSe composites with porphyrins stacked upright on the crystal surface. Porphyrins with four potential ligating sites are able to bind to the crystal surface only if the donors are at the end of sufficiently long and flexible tethers. High-dilution methods allowed the synthesis and isolation of well-defined composites of composition [CdSeporphyrin}(2)], where porphyrin 5,10,15,20-tetrakis3-(carboxy-n-alkyloxy)phenyl}porphyrinato zinc (n = 5 or 10) and 5,10,15,20-tetrakis3-(11-undecenyloxythiol)phenyl}porphyrinato zinc. Comparison of the composition data obtained by H-1 NMR spectroscopy with luminescence quenching behavior suggests a dependence of quenching efficiency On the tether length. Luminescence quenching was also observed for porphyrins that, according to H-1 NMR results, do not undergo surface ligand exchange.