2-((4R,5R)-4-Methoxymethyl-5-phenyl-4,5-dihydro-oxazol-2-yl)-pyridine | 117409-06-0

• 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: 2-((4R,5R)-4-Methoxymethyl-5-phenyl-4,5-dihydro-oxazol-2-yl)-pyridine
• 英文别名: (4R,5R)-4-(methoxymethyl)-5-phenyl-2-pyridin-2-yl-4,5-dihydro-1,3-oxazole
• CAS: 117409-06-0
• 化学式: C₁₆H₁₆N₂O₂
• 分子量: 268.315
• InChiKey: CSOGUHWWFMSCNR-HUUCEWRRSA-N

物化性质

• 沸点：
  200-210 °C(Press: 0.1 Torr)
• 密度：
  1.18±0.1 g/cm3(Predicted)

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：

  ammonium hexafluorophosphate 、 bis(η3-allyl-μ-chloropalladium(II)) 、 2-((4R,5R)-4-Methoxymethyl-5-phenyl-4,5-dihydro-oxazol-2-yl)-pyridine 以 乙醇 为溶剂， 以80%的产率得到(η(3)-allyl)-[(3'S,4'S)-2-(3',4'-dihydro-3'-phenyl-4'-methyloxymethyl-2'-oxazolyl)pyridine-N,N]palladium(II) hexafluorophosphate
  参考文献：
  名称：

  Palladium Complexes with Chiral Oxazoline Ligands. Effect of Chelate Size on Catalytic Allylic Substitutions

  摘要：

  Mono- and bimetallic allylic palladium complexes (1L-5L) with L being chiral bidentate oxazoline ligands (from pyridine (a-d), quinoline (e-g), and piperazine (h)), containing different kinds of allyl groups (1-5), were easily obtained, and their structures in solution were elucidated by NMR spectroscopy. Complex 1d was also characterized by X-ray diffraction. The activity of these complexes in palladium-catalyzed allylic alkylation for acyclic and cyclic substrates was tested. For catalytic systems with ligands a-g, the activity was very high, although the enantioselectivity was low for pyridine derivatives and moderate for quinolino-oxazoline ligands, showing the beneficial effect of chelate size in the latter case. In contrast, the palladium tetraaza catalytic system (Pd/h) exhibited a low activity and a low asymmetric induction. Allylic complexes 1a, 1d, and 1e were also active in the Pd-catalyzed allylic amination, but the activity of these systems was lower than for the alkylations. Under in situ catalytic conditions, the coordination competition of the benzylamine with the bidentate ligand led to different results than using previously isolated precursors.

  DOI：

  10.1021/om990625+
• 作为产物：
  描述：

  (1R,2R)-(-)-2-氨基-1-苯基-1,3-丙二醇 在 sodium methylate 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 2-((4R,5R)-4-Methoxymethyl-5-phenyl-4,5-dihydro-oxazol-2-yl)-pyridine
  参考文献：
  名称：

  Enantioselective hydrosilylation of acetophenone with rhodium / oxazolines catalysts

  摘要：

  DOI：

  10.1016/s0040-4039(01)93469-0

文献信息

• Enantioselective hydrosilylation of acetophenone with rhodium / oxazolines catalysts
  作者：G. Balavoine、J.C. Clinet、I. Lellouche

  DOI：10.1016/s0040-4039(01)93469-0

  日期：——
• Palladium Complexes with Chiral Oxazoline Ligands. Effect of Chelate Size on Catalytic Allylic Substitutions
  作者：Josep Maria Canal、Montserrat Gómez、Francisco Jiménez、Mercè Rocamora、Guillermo Muller、Elisabet Duñach、Delphine Franco、Alicia Jiménez、F. H. Cano

  DOI：10.1021/om990625+

  日期：2000.3.1

  Mono- and bimetallic allylic palladium complexes (1L-5L) with L being chiral bidentate oxazoline ligands (from pyridine (a-d), quinoline (e-g), and piperazine (h)), containing different kinds of allyl groups (1-5), were easily obtained, and their structures in solution were elucidated by NMR spectroscopy. Complex 1d was also characterized by X-ray diffraction. The activity of these complexes in palladium-catalyzed allylic alkylation for acyclic and cyclic substrates was tested. For catalytic systems with ligands a-g, the activity was very high, although the enantioselectivity was low for pyridine derivatives and moderate for quinolino-oxazoline ligands, showing the beneficial effect of chelate size in the latter case. In contrast, the palladium tetraaza catalytic system (Pd/h) exhibited a low activity and a low asymmetric induction. Allylic complexes 1a, 1d, and 1e were also active in the Pd-catalyzed allylic amination, but the activity of these systems was lower than for the alkylations. Under in situ catalytic conditions, the coordination competition of the benzylamine with the bidentate ligand led to different results than using previously isolated precursors.