(-)-2-[(3S,4R,5R)-5-(4-bromophenyl)-2,3-diphenyl-isoxazolidine-4-carbonyl]pyridine-1-oxide | 1261560-04-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (-)-2-[(3S,4R,5R)-5-(4-bromophenyl)-2,3-diphenyl-isoxazolidine-4-carbonyl]pyridine-1-oxide
• 英文别名: 2-((3S,4R,5R)-5-(4-bromophenyl)-2,3-diphenylisoxazolidine-4-carbonyl)pyridine N-oxide；[(3S,4R,5R)-5-(4-bromophenyl)-2,3-diphenyl-1,2-oxazolidin-4-yl]-(1-oxidopyridin-1-ium-2-yl)methanone
• CAS: 1261560-04-6
• 化学式: C₂₇H₂₁BrN₂O₃
• 分子量: 501.379
• InChiKey: VUMAUJGKRQNCKI-WEWMWRJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯甲醛 在 copper(II) bis(trifluoromethanesulfonate) 、 (S,S)-(-)-2,2'-异亚丙基双(4-叔丁基-2-恶唑啉) 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 10.5h， 生成 2-[(3S,4S,5S)-5-(4-bromophenyl)-2,3-diphenyl-isoxazolidine-4-carbonyl]pyridine-1-oxide 、 2-[(3R,4R,5R)-5-(4-bromophenyl)-2,3-diphenyl-isoxazolidine-4-carbonyl]pyridine-1-oxide 、 (-)-2-[(3S,4R,5R)-5-(4-bromophenyl)-2,3-diphenyl-isoxazolidine-4-carbonyl]pyridine-1-oxide
  参考文献：
  名称：

  Highly Enantioselective Nitrone Cycloadditions with 2-Alkenoyl Pyridine N-Oxides Catalyzed by Cu(II)−BOX Complexes

  摘要：

  Enantioselective nitrone cycloadditions with 2-alkenoyl pyridine N-oxides as dipolarophiles have been reported. The reaction is catalyzed by Cu(II)-BOX complexes to give the expected isoxazolidine products with high diastereo- and enantioselectivity.

  DOI：

  10.1021/ol102716e

文献信息

• Enantioselective Cycloadditions of 2‐Alkenoylpyridine‐ <i>N</i> ‐oxides Catalysed by a Bis(oxazoline)/Cu ^II Complex: Structure of the Reactive Intermediate
  作者：Alessandro Livieri、Massimo Boiocchi、Giovanni Desimoni、Giuseppe Faita

  DOI：10.1002/chem.201002017

  日期：2011.1.10

  Diels–Alder and 1,3‐dipolar cycloadditions involving (E)‐3‐aryl‐1‐(pyridin‐2‐yl‐N‐oxide)prop‐2‐en‐1‐ones as the 2π components are efficiently catalysed by bis(oxazoline)–CuII complexes. The cycloadducts are obtained in quantitative yields with up to 98 % ee; absolute configurations were determined by X‐ray analysis. The structure of the reactive complex, determined by X‐ray analysis, is fully consistent

  bis有效地催化了涉及（E）-3-芳基-1-（吡啶-2-基-N-氧化氮）丙-2-烯-1-酮的Diels-Alder和1,3-偶极环加成反应。（恶唑啉）–Cu II配合物。环加合物的定量收率高达98％  ee ; 绝对构型是通过X射线分析确定的。通过X射线分析确定的反应性络合物的结构与催化过程的立体化学结果完全一致（二烯或硝酮接近配位的吡啶-N-氧化物衍生物受阻面较小）。
• Highly Enantioselective Nitrone Cycloadditions with 2-Alkenoyl Pyridine <i>N</i>-Oxides Catalyzed by Cu(II)−BOX Complexes
  作者：Santiago Barroso、Gonzalo Blay、M. Carmen Muñoz、José R. Pedro

  DOI：10.1021/ol102716e

  日期：2011.2.4

  Enantioselective nitrone cycloadditions with 2-alkenoyl pyridine N-oxides as dipolarophiles have been reported. The reaction is catalyzed by Cu(II)-BOX complexes to give the expected isoxazolidine products with high diastereo- and enantioselectivity.