3-(3-hydroxy-3-methyl-1-butynyl)perylene | 224456-78-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 3-(3-hydroxy-3-methyl-1-butynyl)perylene
• 英文别名: 2-Methyl-4-perylen-3-ylbut-3-yn-2-ol
• CAS: 224456-78-4
• 化学式: C₂₅H₁₈O
• 分子量: 334.417
• InChiKey: WZMAMCSBPOIDMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(3-hydroxy-3-methyl-1-butynyl)perylene 在 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 0.17h， 以30%的产率得到3-乙炔基苝
  参考文献：
  名称：

  Nucleobase Recognition by Artificial Receptors Possessing a Ferrocene Skeleton as a Novel Modular Unit for Hydrogen Bonding and Stacking Interactions

  摘要：

  Novel ferrocene-modified artificial nucleobase receptors were designed and synthesized. The nucleobase receptors possess hydrogen-bonding and pi-stacking interaction sites that act simultaneously for binding to 1-butylthymine utilizing the pivot character of the ferrocene skeleton. Diamidopyridine was chosen for the hydrogen-bonding moiety, and various polynuclear aromatics were used for pi-stacking one. The two components were tethered to the cyclopentadienyl rings via ethynediyl and oxymethylene spacers. The binding affinity of the receptors to 1-butylthymine was found to be dependent on the aromatic structures. Thus, the association constants for perylene-linked receptors were approximately doubled compared to those of aromatic-free ones, an energy difference of similar to 0.5 kcal/mol. Detailed comparisons between the 10 receptors clarified the value of the pivot character of the ferrocene for construction of the intermolecular interaction site.

  DOI：

  10.1021/jo982138u
• 作为产物：
  描述：

  3-Aminoperylene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 硫酸 、 potassium iodide 、 sodium nitrite 作用下， 以 various solvent(s) 为溶剂， 反应 23.0h， 生成 3-(3-hydroxy-3-methyl-1-butynyl)perylene
  参考文献：
  名称：

  Nucleobase Recognition by Artificial Receptors Possessing a Ferrocene Skeleton as a Novel Modular Unit for Hydrogen Bonding and Stacking Interactions

  摘要：

  Novel ferrocene-modified artificial nucleobase receptors were designed and synthesized. The nucleobase receptors possess hydrogen-bonding and pi-stacking interaction sites that act simultaneously for binding to 1-butylthymine utilizing the pivot character of the ferrocene skeleton. Diamidopyridine was chosen for the hydrogen-bonding moiety, and various polynuclear aromatics were used for pi-stacking one. The two components were tethered to the cyclopentadienyl rings via ethynediyl and oxymethylene spacers. The binding affinity of the receptors to 1-butylthymine was found to be dependent on the aromatic structures. Thus, the association constants for perylene-linked receptors were approximately doubled compared to those of aromatic-free ones, an energy difference of similar to 0.5 kcal/mol. Detailed comparisons between the 10 receptors clarified the value of the pivot character of the ferrocene for construction of the intermolecular interaction site.

  DOI：

  10.1021/jo982138u

文献信息

• Nucleobase Recognition by Artificial Receptors Possessing a Ferrocene Skeleton as a Novel Modular Unit for Hydrogen Bonding and Stacking Interactions
  作者：Masahiko Inouye、Yutaka Hyodo、Hiroyuki Nakazumi

  DOI：10.1021/jo982138u

  日期：1999.4.1

  Novel ferrocene-modified artificial nucleobase receptors were designed and synthesized. The nucleobase receptors possess hydrogen-bonding and pi-stacking interaction sites that act simultaneously for binding to 1-butylthymine utilizing the pivot character of the ferrocene skeleton. Diamidopyridine was chosen for the hydrogen-bonding moiety, and various polynuclear aromatics were used for pi-stacking one. The two components were tethered to the cyclopentadienyl rings via ethynediyl and oxymethylene spacers. The binding affinity of the receptors to 1-butylthymine was found to be dependent on the aromatic structures. Thus, the association constants for perylene-linked receptors were approximately doubled compared to those of aromatic-free ones, an energy difference of similar to 0.5 kcal/mol. Detailed comparisons between the 10 receptors clarified the value of the pivot character of the ferrocene for construction of the intermolecular interaction site.