2,6-bis[(S)-4-isopropyloxazolin-2-yl]-4-[4-(4-vinylbenzyloxy)phenoxy]pyridine | 862183-15-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-bis[(S)-4-isopropyloxazolin-2-yl]-4-[4-(4-vinylbenzyloxy)phenoxy]pyridine
• 英文别名: (4S)-2-[4-[4-[(4-ethenylphenyl)methoxy]phenoxy]-6-[(4S)-4-propan-2-yl-4,5-dihydro-1,3-oxazol-2-yl]pyridin-2-yl]-4-propan-2-yl-4,5-dihydro-1,3-oxazole
• CAS: 862183-15-1
• 化学式: C₃₂H₃₅N₃O₄
• 分子量: 525.648
• InChiKey: VICCWRAAYOUXAY-LOYHVIPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  74.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-氯吡啶-2,6-二羧酸 在 氯化亚砜 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 、 氯苯 为溶剂， 反应 32.25h， 生成 2,6-bis[(S)-4-isopropyloxazolin-2-yl]-4-[4-(4-vinylbenzyloxy)phenoxy]pyridine
  参考文献：
  名称：

  A Flexible and Versatile Strategy for the Covalent Immobilization of Chiral Catalysts Based on Pyridinebis(oxazoline) Ligands

  摘要：

  Flexible and versatile methods have been developed for the immobilization of chiral pyridinebis(oxazoline) ligands by covalent bonding to a solid support, either by grafting or by polymerization. Different spacers can easily be introduced to modulate the support-ligand distance and the electronic properties of the chiral ligand. As an example, 2,6-bis [(S)-4-isopropyloxazolin-2-yl] pyridine has been immobilized on polystyrene resins, both on a Merrifield-type resin by grafting and on supports prepared by polymerization of 4-vinyl-substituted ligands. The corresponding Ru complexes have been tested as catalysts in the cyclopropanation reaction between styrene and ethyl diazoacetate. The catalytic activity, the enantioselectivity, and the recyclability are strongly dependent on the catalyst preparation method and the total exclusion of oxygen and moisture in the filtration process. Under such optimized conditions, yields over 60% with up to 90% ee can be obtained in four successive reactions-the best cyclopropanation results described to date for a chiral solid ruthenium catalyst.

  DOI：

  10.1021/jo050504l

文献信息

• A Flexible and Versatile Strategy for the Covalent Immobilization of Chiral Catalysts Based on Pyridinebis(oxazoline) Ligands
  作者：Alfonso Cornejo、José M. Fraile、José I. García、María J. Gil、Santiago V. Luis、Víctor Martínez-Merino、José A. Mayoral

  DOI：10.1021/jo050504l

  日期：2005.7.1

  Flexible and versatile methods have been developed for the immobilization of chiral pyridinebis(oxazoline) ligands by covalent bonding to a solid support, either by grafting or by polymerization. Different spacers can easily be introduced to modulate the support-ligand distance and the electronic properties of the chiral ligand. As an example, 2,6-bis [(S)-4-isopropyloxazolin-2-yl] pyridine has been immobilized on polystyrene resins, both on a Merrifield-type resin by grafting and on supports prepared by polymerization of 4-vinyl-substituted ligands. The corresponding Ru complexes have been tested as catalysts in the cyclopropanation reaction between styrene and ethyl diazoacetate. The catalytic activity, the enantioselectivity, and the recyclability are strongly dependent on the catalyst preparation method and the total exclusion of oxygen and moisture in the filtration process. Under such optimized conditions, yields over 60% with up to 90% ee can be obtained in four successive reactions-the best cyclopropanation results described to date for a chiral solid ruthenium catalyst.