4,4'-methylenebis[(4R)-2-phenyl-2-oxazoline] | 1173114-40-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4'-methylenebis[(4R)-2-phenyl-2-oxazoline]
• 英文别名: AraBOX；(4R)-2-phenyl-4-[[(4R)-2-phenyl-4,5-dihydro-1,3-oxazol-4-yl]methyl]-4,5-dihydro-1,3-oxazole
• CAS: 1173114-40-3
• 化学式: C₁₉H₁₈N₂O₂
• 分子量: 306.364
• InChiKey: OIEDFVQROYWLCN-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  43.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N,N'-[(2R,4R)-1,5-bis{[tert-butyl(dimethyl)silyl]oxy}pentane-2,4-diyl]benzamide 在 对甲基苯磺酰氟 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以75%的产率得到4,4'-methylenebis[(4R)-2-phenyl-2-oxazoline]
  参考文献：
  名称：

  Preparation, structure and catalytic activity of copper(II) complexes of novel 4,4′-BOX ligands

  摘要：

  This Letter details the synthesis of two new 4,4'-bisoxazoline (BOX) ligands. The copper(II) complex of one of the new ligands is structurally determined. The catalytic performance of the copper(II) complexes of the novel ligands, and that of our recently described phenyl AraBOX ligand in Diels-Alder reactions are reported. We have used the structural information to propose an explanation of a curious variation in the diastereoselectivity obtained in the case of one ligand complex. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.135
• 作为试剂：
  描述：

  3-[(E)-2-丁酰基]-1,3-噁唑烷-2-酮 、 环戊二烯 在 4,4'-methylenebis[(4R)-2-phenyl-2-oxazoline] 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 3-(3-Methylbicyclo[2.2.1]hept-5-ene-2-carbonyl)-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Preparation, structure and catalytic activity of copper(II) complexes of novel 4,4′-BOX ligands

  摘要：

  This Letter details the synthesis of two new 4,4'-bisoxazoline (BOX) ligands. The copper(II) complex of one of the new ligands is structurally determined. The catalytic performance of the copper(II) complexes of the novel ligands, and that of our recently described phenyl AraBOX ligand in Diels-Alder reactions are reported. We have used the structural information to propose an explanation of a curious variation in the diastereoselectivity obtained in the case of one ligand complex. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.135

文献信息

• The Synthesis of AraBOX, a New 4,4′-Bis(oxazoline), from Novel Pentitol-Derived Bis-β-amino Alcohols
  作者：Patrick O’Leary、David Frain、Fiona Kirby、Patrick McArdle

  DOI：10.1055/s-0029-1216731

  日期：——

  phenyl 4,4'-bis(oxazoline) [AraBOX] is described. The novel ligand is prepared in two efficient steps from a bis-[(O-silyl)β-amino alcohol], via conversion into an intermediate bis(benzamide) followed by a one-pot deprotection-activation-ring closure (DARC) oxazoline formation. To our knowledge, this is the first reported synthesis of an oxazoline ring via this DARC method. The synthesis of two precursor

  描述了新型苯基 ​​4,4'-双(恶唑啉) [AraBOX] 的制备。新型配体由双-[(O-甲硅烷基)β-氨基醇]通过两个有效步骤制备，通过转化为中间体双（苯甲酰胺），然后是一锅脱保护-活化-闭环（DARC）恶唑啉形成。据我们所知，这是首次报道通过这种 DARC 方法合成恶唑啉环。还描述了两种前体双-β-氨基醇的合成，(2R,4R)-和 meso-2,4-diaminopentane-1,5-diol，分别衍生自 D-(+)-arabitol 和木糖醇.