(4''R,2S)-2'-(4'',5''-dihydro-4''-phenyl-2''-oxazolyl)-6'-(2,2-dimethyl-1-hydroxypropyl)pyridine | 164021-89-0

• 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: (4''R,2S)-2'-(4'',5''-dihydro-4''-phenyl-2''-oxazolyl)-6'-(2,2-dimethyl-1-hydroxypropyl)pyridine
• 英文别名: (3'R,1''R)-2-(3'-phenyl)oxazolyl-6-(1''-hydroxy-2,2-dimethyl)propylpyridine；(1S)-2,2-dimethyl-1-[6-[(4R)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]pyridin-2-yl]propan-1-ol
• CAS: 164021-89-0
• 化学式: C₁₉H₂₂N₂O₂
• 分子量: 310.396
• InChiKey: KYDGQQHSSXYHPC-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  54.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(-4-methoxycarbonyloxyphenyl)propionic acid 、 (4''R,2S)-2'-(4'',5''-dihydro-4''-phenyl-2''-oxazolyl)-6'-(2,2-dimethyl-1-hydroxypropyl)pyridine 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 以58%的产率得到3-(4-Methoxycarbonyloxy-phenyl)-propionic acid (S)-2,2-dimethyl-1-[6-((R)-4-phenyl-4,5-dihydro-oxazol-2-yl)-pyridin-2-yl]-propyl ester
  参考文献：
  名称：

  Enantioselective allylic alkylation using polymer-supported palladium catalysts

  摘要：

  Chiral 2'-(4",5"-dihydro-2"-oxazolyl)-6'-(1-hydroxylalkyl)pyridines were grafted via ester-linkages directly to cross-linked polystyrene and to polyethyleneglycol-containing resins TentaGel and ArgoGel functionalized with carboxylic acid groups or via spacers containing a carboxylic acid group. The polymeric ligands were used in the palladium-catalyzed substitution of rac-1,3-diphenyl-2-propenyl acetate with dimethyl malonate. The enantioselectivities (up to 80% ee) were similar to those observed employing an analogous monomeric catalyst. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00416-4
• 作为产物：
  描述：

  D-苯甘氨醇 、 6-(1-Hydroxy-2,2-dimethyl-propyl)-pyridine-2-carboximidic acid methyl ester 在 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (4''R,2S)-2'-(4'',5''-dihydro-4''-phenyl-2''-oxazolyl)-6'-(2,2-dimethyl-1-hydroxypropyl)pyridine 、 (4''R,2R)-2'-(4'',5''-dihydro-4''-phenyl-2''-oxazolyl)-6'-(2,2-dimethyl-1-hydroxypropyl)pyridine
  参考文献：
  名称：

  Enantioselective addition of diethylzinc to aldehydes catalyzed by pyridineoxazolinealcohols

  摘要：

  Chiral 2-pyridylcarbinols carrying chiral oxazolyl substituents in the 6-position of the pyridine ring catalyze the enantioselective addition of diethylzinc to aromatic aldehydes. The absolute configuration of the product alcohol is determined by the configuration at the stereogenic center bearing the alcohol group, the effect of the oxazoline ring being to increase the stereoselectivity. Attempts to use methyl ether derivatives of the same ligands in the rhodium-catalyzed hydrosilylation of acetophenone did not result in any observed enantioselectivity.

  DOI：

  10.1016/0957-4166(95)00039-r

文献信息

• Enantioselective Allylic Substitutions Catalyzed by [(Hydroxyalkyl)pyridinooxazoline]- and [(Alkoxyalkyl)pyridinooxazoline]palladium Complexes
  作者：Kerstin Nordström、Emmanuel Macedo、Christina Moberg

  DOI：10.1021/jo961490+

  日期：1997.3.1

  Highly enantioselective (up to >99% eel palladium-catalyzed substitution of rac-3-diphenyl-2-propenyl acetate with dimethyl malonate as nucleophile was achieved using 2-(1-hydroxyalkyl)-6-(4,5-dihydro-2-oxazolyl)pyridines and 2-(1-alkoxyalkyl)-6-(4,5-dihydro-2-oxazolyl)pyridines as ligands for palladium. The selectivity was found to be highly dependent on the nature of the substituents on the ligand and on the relative configuration of the two stereogenic centers present in the ligand. The results are discussed in terms of the conformation of the ligands in the intermediate pi-allylpalladium complexes.