(3S,3aR,4S,5R)-3-phenylsulfonyl-4,5-isopropylidenedioxy-hexahydropyrrolo[1,2-b]isoxazole | 1369963-66-5

• 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: (3S,3aR,4S,5R)-3-phenylsulfonyl-4,5-isopropylidenedioxy-hexahydropyrrolo[1,2-b]isoxazole
• 英文别名: (1R,2S,6R,11S)-11-(benzenesulfonyl)-4,4-dimethyl-3,5,9-trioxa-8-azatricyclo[6.3.0.02,6]undecane
• CAS: 1369963-66-5
• 化学式: C₁₅H₁₉NO₅S
• 分子量: 325.386
• InChiKey: KAWMIMLNBHNVDB-YIYPIFLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  73.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S,3aR,4S,5R)-3-phenylsulfonyl-4,5-isopropylidenedioxy-hexahydropyrrolo[1,2-b]isoxazole 以 甲苯 为溶剂， 反应 72.0h， 以100%的产率得到(3R,3aR,4S,5R)-3-phenylsulfonyl-4,5-isopropylidenedioxy-hexahydropyrrolo[1,2-b]isoxazole
  参考文献：
  名称：

  1,3-Dipolar cycloaddition of nitrones with phenylvinyl sulfone. An experimental and theoretical study

  摘要：

  The addition of three nitrones to phenylvinylsulfone, 1, has been studied. The stereochemistry previously established by two-dimensional NMR techniques was confirmed by X-ray crystal structure determination. Theoretical studies made us propose that this reaction is not purely regioselective, but by controlling the substituents of nitrone and temperature the regioselectivity increases. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.01.006
• 作为产物：
  描述：

  苯基乙烯基砜 、 (2S,3R)-3,4-cis-isopropylidenedioxypyrroline N-oxid 以 甲苯 为溶剂， 反应 6.0h， 生成 (3R,3aR,4S,5R)-3-phenylsulfonyl-4,5-isopropylidenedioxy-hexahydropyrrolo[1,2-b]isoxazole 、 (3S,3aR,4S,5R)-3-phenylsulfonyl-4,5-isopropylidenedioxy-hexahydropyrrolo[1,2-b]isoxazole 、 (2S,3aS,4S,5R)-2-phenylsulfonyl-4,5-isopropylidenedioxy-hexahydropyrrolo[1,2-b]isoxazole 、 (2R,3aS,4S,5R)-2-pchenylsulfonyl-4,5-isopropylidenedioxy-hexahydropyrrolo[1,2-b]isoxazole
  参考文献：
  名称：

  手性吡咯烷类化合物合成中的多米诺消除/亲核加成

  摘要：

  多羟基化的吡咯烷是通过一锅法通过将有机金属试剂添加到异恶唑烷中而合成的，该异恶唑烷是通过在硝酮和乙烯基砜之间进行1,3-偶极环加成而获得的。该方法突出了砜的反应性，并为使用环状亚胺作为关键中间体制备手性吡咯烷提供了简便的方法。

  DOI：

  10.1021/jo400873c

文献信息

• Domino Elimination/Nucleophilic Addition in the Synthesis of Chiral Pyrrolidines
  作者：MariFe Flores、Pilar García-García、Narciso M. Garrido、Isidro S. Marcos、Francisca Sanz-González、David Díez

  DOI：10.1021/jo400873c

  日期：2013.7.19

  Polyhydroxylated pyrrolidines have been synthesized in a one-pot procedure by the addition of an organometallic reagent to isoxazolidines obtained by a 1,3-dipolar cycloaddition between nitrones and vinylsulfones. This method highlights sulfone reactivity and provides an easy approach for the preparation of chiral pyrrolidines using cyclic imines as key intermediates.

  多羟基化的吡咯烷是通过一锅法通过将有机金属试剂添加到异恶唑烷中而合成的，该异恶唑烷是通过在硝酮和乙烯基砜之间进行1,3-偶极环加成而获得的。该方法突出了砜的反应性，并为使用环状亚胺作为关键中间体制备手性吡咯烷提供了简便的方法。
• 1,3-Dipolar cycloaddition of nitrones with phenylvinyl sulfone. An experimental and theoretical study
  作者：MariFe Flores、Pilar García、Narciso M. Garrido、Carlos T. Nieto、Pilar Basabe、Isidro S. Marcos、Francisca Sanz-González、Jonathan M. Goodman、David Díez

  DOI：10.1016/j.tetasy.2012.01.006

  日期：2012.1

  The addition of three nitrones to phenylvinylsulfone, 1, has been studied. The stereochemistry previously established by two-dimensional NMR techniques was confirmed by X-ray crystal structure determination. Theoretical studies made us propose that this reaction is not purely regioselective, but by controlling the substituents of nitrone and temperature the regioselectivity increases. (C) 2012 Elsevier Ltd. All rights reserved.