benzyl 3,10b-dihydrobenzo[e]pyrrolo[1,2-c][1,2,3]oxathiazine-1-carboxylate 5,5-dioxide | 1449600-58-1

• 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: benzyl 3,10b-dihydrobenzo[e]pyrrolo[1,2-c][1,2,3]oxathiazine-1-carboxylate 5,5-dioxide
• 英文别名: Benzyl 5,5-dioxo-3,10b-dihydropyrrolo[1,2-c][1,2,3]benzoxathiazine-1-carboxylate；benzyl 5,5-dioxo-3,10b-dihydropyrrolo[1,2-c][1,2,3]benzoxathiazine-1-carboxylate
• CAS: 1449600-58-1
• 化学式: C₁₈H₁₅NO₅S
• 分子量: 357.387
• InChiKey: UYIKPDWOVXGNFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl 3,10b-dihydrobenzo[e]pyrrolo[1,2-c][1,2,3]oxathiazine-1-carboxylate 5,5-dioxide 在 magnesium 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.0h， 以82%的产率得到
  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
• 作为产物：
  描述：

  benzo[e][1,2,3]oxathiazine 2,2-dioxide 、 buta-2,3-dienoic acid benzyl ester 在 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以99%的产率得到benzyl 3,10b-dihydrobenzo[e]pyrrolo[1,2-c][1,2,3]oxathiazine-1-carboxylate 5,5-dioxide
  参考文献：
  名称：

  磷烷催化 [3+2] 环加成反应的苯甲酸酯和环亚胺：一种合成苯并稠合环磺酰胺杂环的简单有效方法

  摘要：

  通过使用磷烷作为有机催化剂，通过烯丙酸酯和环状亚胺（包括环状三氟甲基酮亚胺）的环加成反应开发了苯并稠合环状磺酰胺杂环的有效合成，产率高（71-97%）。该反应也可以方便地以克规模进行。此外，已经公开了磺酰胺杂环产物的一些简单转化以获得官能胺。通过筛选作为有机催化剂的几种市售手性磷烷配体，还尝试了该反应的不对称变体，获得了高达 36% 的 ee。

  DOI：

  10.1002/ejoc.201201756

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.
• Phosphane-Catalyzed [3+2] Cycloaddition Reaction of Allenoate and Cyclic Imines: A Simple and Efficient Method for Synthesis of Benzo-Fused Cyclic Sulfamidate Heterocycles
  作者：You-Qing Wang、Yongna Zhang、Haina Dong、Jie Zhang、Jin Zhao

  DOI：10.1002/ejoc.201201756

  日期：2013.6

  organocatalyst, an efficient synthesis of benzo-fused cyclic sulfamidate heterocycles has been developed through a cycloaddition reaction of allenoate and cyclic imines including cyclic trifluoromethyl ketimine, which gave high yields (71–97 %). The reaction could also be conveniently performed on a gram scale. Furthermore, some simple transformations of the sulfamidate heterocycle products have been

  通过使用磷烷作为有机催化剂，通过烯丙酸酯和环状亚胺（包括环状三氟甲基酮亚胺）的环加成反应开发了苯并稠合环状磺酰胺杂环的有效合成，产率高（71-97%）。该反应也可以方便地以克规模进行。此外，已经公开了磺酰胺杂环产物的一些简单转化以获得官能胺。通过筛选作为有机催化剂的几种市售手性磷烷配体，还尝试了该反应的不对称变体，获得了高达 36% 的 ee。