(4'R)-2-(3',4'-dihydro-4'-phenyl-2'-oxazolyl)-6-(methoxymethyl)pyridine | 220108-60-1

• 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)-2-(3',4'-dihydro-4'-phenyl-2'-oxazolyl)-6-(methoxymethyl)pyridine
• 英文别名: (4R)-2-[6-(methoxymethyl)pyridin-2-yl]-4-phenyl-4,5-dihydro-1,3-oxazole
• CAS: 220108-60-1
• 化学式: C₁₆H₁₆N₂O₂
• 分子量: 268.315
• InChiKey: JTNJIBIUKRCVOI-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  43.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二(氰基苯)二氯化钯 、 (4'R)-2-(3',4'-dihydro-4'-phenyl-2'-oxazolyl)-6-(methoxymethyl)pyridine 以 苯 为溶剂， 生成 [(4'R)-2-(3',4'-dihydro-4'-phenyl-2'-oxazolyl)-6-(methoxymethyl)pyridine]palladium(II) chloride
  参考文献：
  名称：

  (Hydroxyalkyl)pyridinooxazolines in Palladium-Catalyzed Allylic Substitutions. Conformational Preferences of the Ligand

  摘要：

  2-(3',4'-Dihydro-2'-oxazolyl)-6-(hydroxymethyl)pyridines have been shown by X-ray crystallographic analysis and DFT calculations to exhibit two conformational minima in their complexes with Pd(II) chloride. Theoretical studies of (pi-allyl)palladium(II) and (pi-olefin)palladium(0) complexes with 2-(3',4'-dihydro-2'-oxazolyl)-6-(hydroxymethyl)pyridine revealed two minima in each complex. In contrast, in the calculations of the Pd(II) chloride and Pd(II) allyl complexes of 2-(3',4'-dihydro-2'-oxazolyl)-6-(methoxymethyl)pyridine a single conformational minimum was found. NOE studies of complexes in solution were in agreement with the results obtained by the theoretical studies. The knowledge about the conformational preferences of the palladium complexes with (hydroxyalkyl)pyridinooxazolines and (methoxyalkyl)pyridinooxazolines is used to rationalize the results of palladium-catalyzed allylic alkylations employing the two types of ligands.

  DOI：

  10.1021/om990552u
• 作为产物：
  描述：

  6-羟甲基-2-氰基吡啶 在 甲醇 、 硫酸 、 sodium methylate 、 sodium hydride 作用下， 反应 29.0h， 生成 (4'R)-2-(3',4'-dihydro-4'-phenyl-2'-oxazolyl)-6-(methoxymethyl)pyridine
  参考文献：
  名称：

  Palladium-catalyzed allylic alkylation using pyridino-oxazolines and quinolino-oxazolines as ligands—influence of steric factors

  摘要：

  Four new chiral pyridino- and quinolino-oxazolines were subjected to the palladium-catalyzed alkylation of 1,3-diphenyl-2-propenyl acetate. The enantioselectivity varied (82-88% ee) with the steric properties of the ligands. The results are discussed in connection with results previously obtained using analogous ligands. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00346-2
• 作为试剂：
  描述：

  (±)-反式-1,3-二苯基烯丙基乙酸酯 、 丙二酸二甲酯 在 N,O-双三甲硅基乙酰胺 、 bis(η3-allyl-μ-chloropalladium(II)) 、 potassium acetate 、 (4'R)-2-(3',4'-dihydro-4'-phenyl-2'-oxazolyl)-6-(methoxymethyl)pyridine 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 生成 dimethyl 2-[(E)-(S)-1,3-diphenylallyl]-malonate 、 (R)-methyl 2-carbomethoxy-3,5-diphenylpent-4-enoate
  参考文献：
  名称：

  Palladium-catalyzed allylic alkylation using pyridino-oxazolines and quinolino-oxazolines as ligands—influence of steric factors

  摘要：

  Four new chiral pyridino- and quinolino-oxazolines were subjected to the palladium-catalyzed alkylation of 1,3-diphenyl-2-propenyl acetate. The enantioselectivity varied (82-88% ee) with the steric properties of the ligands. The results are discussed in connection with results previously obtained using analogous ligands. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00346-2