(3R,3aR,8aS,8bS)-3-ethoxy-3a,6,7,8,8a,8b-hexahydrofuro[3,4-d]pyrrolo[1,2-b]isoxazol-1(3H)-one | 869809-08-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3R,3aR,8aS,8bS)-3-ethoxy-3a,6,7,8,8a,8b-hexahydrofuro[3,4-d]pyrrolo[1,2-b]isoxazol-1(3H)-one
• 英文别名: (1S,2S,5R,6R)-5-ethoxy-4,7-dioxa-8-azatricyclo[6.3.0.02,6]undecan-3-one
• CAS: 869809-08-5
• 化学式: C₁₀H₁₅NO₄
• 分子量: 213.233
• InChiKey: CQVYKTGOVVJXRL-QHOPCYEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,3aR,8aS,8bS)-3-ethoxy-3a,6,7,8,8a,8b-hexahydrofuro[3,4-d]pyrrolo[1,2-b]isoxazol-1(3H)-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (2R,3R)-3-[(2'S)-pyrrolidin-2-yl]butan-1,2,4-triol
  参考文献：
  名称：

  The Role of the Sulfinyl Group on the Course of the Reactions of 3-p-Tolylsulfinylfuran-2(5H)-ones with Nitrones. Synthetic Uses of Cycloreversion Processes

  摘要：

  The reaction of enantiopure 3-p-tolylsulfinylfuran-2(5H)-ones (2a and 2b) with cyclic (4) and acyclic (6) nitrones afforded furoisoxazolidines (5 and 7) in high yields under mild conditions. The reactivity of the dipolarophile was dramatically enhanced by the sulfinyl group, which modulated the pi-facial selectivity (it was complete for reactions from 2b, yielding only the anti adducts) and was the main controller of the endo/exo selectivity. Cycloreversion processes from the resulting sulfinyl furoisoxazolidines proceeded readily and were to be considered to account for an improvement in the selectivity (facial and endo/exo) and even for an inversion of it when the composition of the reaction mixtures obtained under kinetic and thermodynamic conditions were quite different.

  DOI：

  10.1021/jo0513111
• 作为产物：
  描述：

  (R₅,S_S)-5-ethoxy-3-(p-tolylsulfinyl)furan-2(5H)-one 在 aluminium amalgam 、 水 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.5h， 生成 (3R,3aR,8aS,8bS)-3-ethoxy-3a,6,7,8,8a,8b-hexahydrofuro[3,4-d]pyrrolo[1,2-b]isoxazol-1(3H)-one
  参考文献：
  名称：

  The Role of the Sulfinyl Group on the Course of the Reactions of 3-p-Tolylsulfinylfuran-2(5H)-ones with Nitrones. Synthetic Uses of Cycloreversion Processes

  摘要：

  The reaction of enantiopure 3-p-tolylsulfinylfuran-2(5H)-ones (2a and 2b) with cyclic (4) and acyclic (6) nitrones afforded furoisoxazolidines (5 and 7) in high yields under mild conditions. The reactivity of the dipolarophile was dramatically enhanced by the sulfinyl group, which modulated the pi-facial selectivity (it was complete for reactions from 2b, yielding only the anti adducts) and was the main controller of the endo/exo selectivity. Cycloreversion processes from the resulting sulfinyl furoisoxazolidines proceeded readily and were to be considered to account for an improvement in the selectivity (facial and endo/exo) and even for an inversion of it when the composition of the reaction mixtures obtained under kinetic and thermodynamic conditions were quite different.

  DOI：

  10.1021/jo0513111

文献信息

• The Role of the Sulfinyl Group on the Course of the Reactions of 3-<i>p</i>-Tolylsulfinylfuran-2(5<i>H</i>)-ones with Nitrones. Synthetic Uses of Cycloreversion Processes
  作者：José L. García Ruano、Alberto Fraile、Ana M. Martín Castro、M. Rosario Martín

  DOI：10.1021/jo0513111

  日期：2005.10.1

  The reaction of enantiopure 3-p-tolylsulfinylfuran-2(5H)-ones (2a and 2b) with cyclic (4) and acyclic (6) nitrones afforded furoisoxazolidines (5 and 7) in high yields under mild conditions. The reactivity of the dipolarophile was dramatically enhanced by the sulfinyl group, which modulated the pi-facial selectivity (it was complete for reactions from 2b, yielding only the anti adducts) and was the main controller of the endo/exo selectivity. Cycloreversion processes from the resulting sulfinyl furoisoxazolidines proceeded readily and were to be considered to account for an improvement in the selectivity (facial and endo/exo) and even for an inversion of it when the composition of the reaction mixtures obtained under kinetic and thermodynamic conditions were quite different.