(S)-6'-(4-phenyloxazolin-2-yl)-2,2'-bipyridine-6-carboxylic acid | 1237526-58-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (S)-6'-(4-phenyloxazolin-2-yl)-2,2'-bipyridine-6-carboxylic acid
• 英文别名: S-Phbipox；S-PhbipoxH；6-[6-[(4S)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]pyridin-2-yl]pyridine-2-carboxylic acid
• CAS: 1237526-58-7
• 化学式: C₂₀H₁₅N₃O₃
• 分子量: 345.357
• InChiKey: XQSKWINGAAGQIK-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  84.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-6'-(4-phenyloxazolin-2-yl)-2,2'-bipyridine-6-carboxylic acid 、 europium(III) trifluoromethanesulfonate 在 triethylamine 作用下， 以 乙腈 为溶剂， 以81%的产率得到[Eu.cntnd.(Λ-Eu((S)-6'-(4-phenyloxazolin-2-yl)-2,2'-bipyridine-6-carboxylate)2-Δ-Eu((S)-6'-(4-phenyloxazolin-2-yl)-2,2'-bipyridine-6-carboxylate)2)3](OTf)9
  参考文献：
  名称：

  Metal-Controlled Diastereoselective Self-Assembly and Circularly Polarized Luminescence of a Chiral Heptanuclear Europium Wheel

  摘要：

  The chiral dissymmetric tetradentate ligand (S)-6'-(4-phenyloxazolin-2-yl)-2,2'-bipyridine-6-carboxylate (S-Phbipox) leads to the diastereoselective assembly of a homochiral Eu3+ triangle and a highly emissive (quantum yield = 27%) heptanuclear wheel that is the largest example of a chiral luminescent complex of Eu3+ reported to date. The nuclearity of the assembly is controlled by the solvent and the Eu3+ cation. All of the compounds show large circularly polarized luminescence with an activity that varies with the nature of the assembly (highest for the homochiral trimer).

  DOI：

  10.1021/ja3020814
• 作为产物：
  描述：

  ethyl (S)-6'-((2-chloro-1-phenylethyl)amido)-2,2'-bipyridine-6-carboxylate 在 potassium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 48.0h， 以73%的产率得到(S)-6'-(4-phenyloxazolin-2-yl)-2,2'-bipyridine-6-carboxylic acid
  参考文献：
  名称：

  联苯并恶唑啉的手性Euro三角形的非对映选择性自组装？羧酸盐配体

  摘要：

  同手性三角形：一个对映纯的triangle三角形，是根据浓度依赖的过程从新的联苯并恶唑啉羧酸盐配体中选择性地自组装而成的（请参见方案）。

  DOI：

  10.1002/chem.201000572

文献信息

• Diastereoselective Self-Assembly of a Homochiral Europium Triangle from a BipyoxazolineCarboxylate Ligand
  作者：Gülay Bozoklu、Claire Marchal、Christelle Gateau、Jacques Pécaut、Daniel Imbert、Marinella Mazzanti

  DOI：10.1002/chem.201000572

  日期：——

  A homochiral triangle: An enantiopure europium triangle selectively self‐assembles from a new bipyoxazolinecarboxylate ligand in a concentration‐dependent process (see scheme).

  同手性三角形：一个对映纯的triangle三角形，是根据浓度依赖的过程从新的联苯并恶唑啉羧酸盐配体中选择性地自组装而成的（请参见方案）。
• Metal-Controlled Diastereoselective Self-Assembly and Circularly Polarized Luminescence of a Chiral Heptanuclear Europium Wheel
  作者：Gülay Bozoklu、Christelle Gateau、Daniel Imbert、Jacques Pécaut、Koen Robeyns、Yaroslav Filinchuk、Farah Memon、Gilles Muller、Marinella Mazzanti

  DOI：10.1021/ja3020814

  日期：2012.5.23

  The chiral dissymmetric tetradentate ligand (S)-6'-(4-phenyloxazolin-2-yl)-2,2'-bipyridine-6-carboxylate (S-Phbipox) leads to the diastereoselective assembly of a homochiral Eu3+ triangle and a highly emissive (quantum yield = 27%) heptanuclear wheel that is the largest example of a chiral luminescent complex of Eu3+ reported to date. The nuclearity of the assembly is controlled by the solvent and the Eu3+ cation. All of the compounds show large circularly polarized luminescence with an activity that varies with the nature of the assembly (highest for the homochiral trimer).