3-tert-butyl-2-hydroxy-5-(3'-pyridyl)benzaldehyde | 342037-23-4

• 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: 3-tert-butyl-2-hydroxy-5-(3'-pyridyl)benzaldehyde
• 英文别名: 3-(1,1-Dimethylethyl)-2-hydroxy-5-(3-pyridinyl)benzaldehyde；3-tert-butyl-2-hydroxy-5-pyridin-3-ylbenzaldehyde
• CAS: 342037-23-4
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: QLJRZBCJQLJLSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Cis-1,2-diaminocyclohexane 、 3-tert-butyl-2-hydroxy-5-(3'-pyridyl)benzaldehyde 以 乙醇 为溶剂， 反应 16.0h， 以34%的产率得到meso-1,2-diaminocyclohexane-N,N'-bis(3-tert-butyl-5-(3'-pyridyl)salicylidene)
  参考文献：
  名称：

  Directed Assembly of Transition-Metal-Coordinated Molecular Loops and Squares from Salen-Type Components. Examples of Metalation-Controlled Structural Conversion

  摘要：

  A series of transition-metal-containing molecular "loops" and "squares" has been prepared via a directed-assembly approach and characterized. The molecular loops were prepared from the reaction of cis-(PEt3)(2)Pt(OTf)(2) with bis(4-pyridyl)-functionalized free-base salen-type ligands. Zn(II)-metalation of the salen-type ligands in the molecular loops converts the loops to molecular squares. Alternatively, the squares can be obtained by the directed assembly of cis-(PEt3)2Pt(OTf)2 and bis(4-pyridyl)-functionalized Zn(II)salen-type ligands. A concentration-dependent dynamic equilibrium between cyclic species was observed when bis(3-pyridyl)-functionalized free-base salen-type ligand was employed in the reaction. Zn(II) or Cr(III) metalation of the free-base ligand shifted the equilibrium to the single dimeric species. The incorporation of multiple reactive metal sites into a single, cavity-containing supramolecular structure points toward catalytic applications for these new assemblies.

  DOI：

  10.1021/ja037378s
• 作为产物：
  描述：

  5-溴-3-叔丁基-2-羟基苯甲醛 、 diethyl (3-pyridyl)borane 在 sodium hydroxide 、 四(三苯基膦)钯 、 四丁基溴化铵 作用下， 以 四氢呋喃 为溶剂， 以64%的产率得到3-tert-butyl-2-hydroxy-5-(3'-pyridyl)benzaldehyde
  参考文献：
  名称：

  A general route to pyridine-modified salicylaldehydes via Suzuki coupling

  摘要：

  An efficient method for the preparation of 5-(3-pyridyl)- and 5-(4-pyridyl)salicylaldehydes by the palladium-catalyzed cross-coupling reaction of either 4-pyridylboronic acid or diethyl-(3-pyridyl)borane and bromosalicylaldehydes is described. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)00106-x

文献信息

• Directed Assembly of Transition-Metal-Coordinated Molecular Loops and Squares from Salen-Type Components. Examples of Metalation-Controlled Structural Conversion
  作者：Shih-Sheng Sun、Charlotte L. Stern、SonBinh T. Nguyen、Joseph T. Hupp

  DOI：10.1021/ja037378s

  日期：2004.5.1

  A series of transition-metal-containing molecular "loops" and "squares" has been prepared via a directed-assembly approach and characterized. The molecular loops were prepared from the reaction of cis-(PEt3)(2)Pt(OTf)(2) with bis(4-pyridyl)-functionalized free-base salen-type ligands. Zn(II)-metalation of the salen-type ligands in the molecular loops converts the loops to molecular squares. Alternatively, the squares can be obtained by the directed assembly of cis-(PEt3)2Pt(OTf)2 and bis(4-pyridyl)-functionalized Zn(II)salen-type ligands. A concentration-dependent dynamic equilibrium between cyclic species was observed when bis(3-pyridyl)-functionalized free-base salen-type ligand was employed in the reaction. Zn(II) or Cr(III) metalation of the free-base ligand shifted the equilibrium to the single dimeric species. The incorporation of multiple reactive metal sites into a single, cavity-containing supramolecular structure points toward catalytic applications for these new assemblies.
• A general route to pyridine-modified salicylaldehydes via Suzuki coupling
  作者：Gregory A. Morris、SonBinh T. Nguyen

  DOI：10.1016/s0040-4039(01)00106-x

  日期：2001.3

  An efficient method for the preparation of 5-(3-pyridyl)- and 5-(4-pyridyl)salicylaldehydes by the palladium-catalyzed cross-coupling reaction of either 4-pyridylboronic acid or diethyl-(3-pyridyl)borane and bromosalicylaldehydes is described. (C) 2001 Published by Elsevier Science Ltd.