Propan-2-yl 5,5-dioxo-3,10b-dihydropyrrolo[1,2-c][1,2,3]benzoxathiazine-1-carboxylate | 1449600-54-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: Propan-2-yl 5,5-dioxo-3,10b-dihydropyrrolo[1,2-c][1,2,3]benzoxathiazine-1-carboxylate
• 英文别名: propan-2-yl 5,5-dioxo-3,10b-dihydropyrrolo[1,2-c][1,2,3]benzoxathiazine-1-carboxylate
• CAS: 1449600-54-7
• 化学式: C₁₄H₁₅NO₅S
• 分子量: 309.343
• InChiKey: IMOUMENBMPAAOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  benzo[e][1,2,3]oxathiazine 2,2-dioxide 、 isopropyl 2,3-butadienoate 在 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以86%的产率得到Propan-2-yl 5,5-dioxo-3,10b-dihydropyrrolo[1,2-c][1,2,3]benzoxathiazine-1-carboxylate
  参考文献：
  名称：

  Phosphine-Catalyzed [3 + 2] Cycloaddition of Sulfamate-Derived Cyclic Imines with Allenoate: Synthesis of Sulfamate-Fused Dihydropyrroles

  摘要：

  Ph3P-catalyzed [3 + 2] cycloaddition reaction of sulfamate-derived cyclic;mines with allenoate has been developed, affording sulfamate-fused dihydropyrroles under very mild conditions in high yields. Using amino acid-based bifunctional phosphine as chiral catalyst, its asymmetric variant provided the corresponding products in good yields with moderate to excellent enantiomeric excesses (up to 91% yield and up to 98% ee). Subsequent transformations of the heterocyclic products gave various pharmaceutically attractive compounds.

  DOI：

  10.1021/jo401107v

文献信息

• Phosphine-Catalyzed [3 + 2] Cycloaddition of Sulfamate-Derived Cyclic Imines with Allenoate: Synthesis of Sulfamate-Fused Dihydropyrroles
  作者：Hao Yu、Lei Zhang、Zhilin Yang、Zhen Li、Yan Zhao、Yumei Xiao、Hongchao Guo

  DOI：10.1021/jo401107v

  日期：2013.9.6

  Ph3P-catalyzed [3 + 2] cycloaddition reaction of sulfamate-derived cyclic;mines with allenoate has been developed, affording sulfamate-fused dihydropyrroles under very mild conditions in high yields. Using amino acid-based bifunctional phosphine as chiral catalyst, its asymmetric variant provided the corresponding products in good yields with moderate to excellent enantiomeric excesses (up to 91% yield and up to 98% ee). Subsequent transformations of the heterocyclic products gave various pharmaceutically attractive compounds.