(4''R)-2'-(4'',5''-dihydro-4''-phenyl-2''-oxazolyl)-6'-(hydroxymethyl)pyridine | 220108-58-7

• 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'-(4'',5''-dihydro-4''-phenyl-2''-oxazolyl)-6'-(hydroxymethyl)pyridine
• 英文别名: (4'R)-2-(3',4'-dihydro-4'-phenyl-2'-oxazolyl)-6-(hydroxymethyl)pyridine；(4'R)-2-(4',5'-dihydro-4'-phenyl-2'-oxazolyl)-6-(hydroxymethyl)pyridine；[6-[(4R)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]pyridin-2-yl]methanol
• CAS: 220108-58-7
• 化学式: C₁₅H₁₄N₂O₂
• 分子量: 254.288
• InChiKey: LNNGKZPPUMMKCV-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  (4''R)-2'-(4'',5''-dihydro-4''-phenyl-2''-oxazolyl)-6'-(hydroxymethyl)pyridine 在 ammonium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 7.5h， 生成 [6-[(4R)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]pyridin-2-yl]methyl 4-hydroxybenzoate
  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：

  6-羟甲基-2-氰基吡啶 在 硫酸 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 生成 (4''R)-2'-(4'',5''-dihydro-4''-phenyl-2''-oxazolyl)-6'-(hydroxymethyl)pyridine
  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

文献信息

• Dendritic Oxazoline Ligands in Enantioselective Palladium-Catalyzed Allylic Alkylations
  作者：Michael Malkoch、Kristina Hallman、Serghey Lutsenko、Anders Hult、Eva Malmström、Christina Moberg

  DOI：10.1021/jo0200116

  日期：2002.11.1

  attached to 2-(hydroxymethyl)pyridinooxazoline and bis[4-(hydroxymethyl)oxazoline] compounds. The new ligands obtained were assessed in palladium-catalyzed allylic alkylations. The first type of ligands exhibited enantioselectivity similar to that of a benzoyl ester derivative, whereas the latter type of ligands afforded products with higher selectivity than the analogous benzoyl ester. The activity of the

  将基于2,2-双（羟甲基）丙酸和（1R，2S，5R）-薄荷氧基乙酸的第一至第四代树状取代基连接至2-（羟甲基）吡啶并恶唑啉和双[4-（羟甲基）恶唑啉]化合物。在钯催化的烯丙基烷基化反应中评估获得的新配体。第一种配体表现出与苯甲酸酯衍生物相似的对映选择性，而后一种配体提供了比类似苯甲酸酯更高选择性的产物。树突状催化剂的活性随着生成的增加而降低。
• Palladium-catalyzed allylic alkylation using pyridino-oxazolines and quinolino-oxazolines as ligands—influence of steric factors
  作者：Ulf Bremberg、Fredrik Rahm、Christina Moberg

  DOI：10.1016/s0957-4166(98)00346-2

  日期：1998.10

  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.
• Chiral ditopic receptors. Application to palladium-catalyzed allylic alkylation
  作者：Jean Bourguignon、Ulf Bremberg、Georges Dupas、Kristina Hallman、Lars Hagberg、Laurent Hortala、Vincent Levacher、Serghey Lutsenko、Emmanuel Macedo、Christina Moberg、Guy Quéguiner、Fredrik Rahm

  DOI：10.1016/j.tet.2003.10.005

  日期：2003.11

  Chiral pyridinooxazoline, quinolinooxazoline, bis(oxazolino)pyridine (pybox), and bisoxazoline (box) derivatives containing crown ether residues were prepared. Some of the ligands were assessed in substrate binding studies and in palladium catalyzed allylic alkylations. (C) 2003 Elsevier Ltd. All rights reserved.
• (Hydroxyalkyl)pyridinooxazolines in Palladium-Catalyzed Allylic Substitutions. Conformational Preferences of the Ligand
  作者：Mats Svensson、Ulf Bremberg、Kristina Hallman、Ingeborg Csöregh、Christina Moberg

  DOI：10.1021/om990552u

  日期：1999.11.1

  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.