methyl (S)-2-(2-bromo-5,5-dioxidodibenzo[b,g][1,4,5]oxathiazocin-6(7H)-yl)-3-methylbutanoate | 1225039-99-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (S)-2-(2-bromo-5,5-dioxidodibenzo[b,g][1,4,5]oxathiazocin-6(7H)-yl)-3-methylbutanoate
• 英文别名: methyl (2S)-2-(7-bromo-10,10-dioxo-12H-benzo[d][6,1,2]benzoxathiazocin-11-yl)-3-methylbutanoate
• CAS: 1225039-99-5
• 化学式: C₁₉H₂₀BrNO₅S
• 分子量: 454.341
• InChiKey: RYFGLXTWGYHFPM-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  (S)-methyl 2-(4-bromo-2-fluorophenylsulfonamido)-3-methylbutanoate 、 Acetic acid 2-(tert-butyl-dimethyl-silanyloxy)-benzyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以94%的产率得到methyl (S)-2-(2-bromo-5,5-dioxidodibenzo[b,g][1,4,5]oxathiazocin-6(7H)-yl)-3-methylbutanoate
  参考文献：
  名称：

  A Formal [4 + 4] Complementary Ambiphile Pairing Reaction: A New Cyclization Pathway for ortho-Quinone Methides

  摘要：

  A formal, one-pot [4 + 4] cyclization pathway for the generation of eight-membered sultams via in situ generation of an ortho-quinone methide (o-QM) is reported. The pairing of ambiphilic synthons in a complementary fashion is examined whereby o-fluorobenzenesulfonamides are merged with in situ generated o-QM in a formal [4 + 4] cyclization pathway to afford 5,2,1-dibenzooxathiazocine-2,2-dioxide scaffolds under microwave (mW) conditions. The method reported represents the first use of an o-QM in a formal hetero [4 + 4] cyclization.

  DOI：

  10.1021/ol100495w

文献信息

• A Formal [4 + 4] Complementary Ambiphile Pairing Reaction: A New Cyclization Pathway for <i>ortho</i>-Quinone Methides
  作者：Thiwanka B. Samarakoon、Moon Y. Hur、Ryan D. Kurtz、Paul R. Hanson

  DOI：10.1021/ol100495w

  日期：2010.5.21

  A formal, one-pot [4 + 4] cyclization pathway for the generation of eight-membered sultams via in situ generation of an ortho-quinone methide (o-QM) is reported. The pairing of ambiphilic synthons in a complementary fashion is examined whereby o-fluorobenzenesulfonamides are merged with in situ generated o-QM in a formal [4 + 4] cyclization pathway to afford 5,2,1-dibenzooxathiazocine-2,2-dioxide scaffolds under microwave (mW) conditions. The method reported represents the first use of an o-QM in a formal hetero [4 + 4] cyclization.