3-chloro-5-trifluoromethanesulfonoxy-4H-1,2,6-thiadiazin-4-one | 1338699-66-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 3-chloro-5-trifluoromethanesulfonoxy-4H-1,2,6-thiadiazin-4-one
• 英文别名: 3-chloro-5-triflate-4H-1,2,6-thiadiazin-4-one；3-Chloro-5-(trifluoromethylsulfonyloxy)-4H-1,2,6-thiadiazine-4-one；(5-chloro-4-oxo-1,2,6-thiadiazin-3-yl) trifluoromethanesulfonate
• CAS: 1338699-66-3
• 化学式: C₄ClF₃N₂O₄S₂
• 分子量: 296.635
• InChiKey: DRINRKYXSNMRNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-chloro-5-trifluoromethanesulfonoxy-4H-1,2,6-thiadiazin-4-one 在 四乙基溴化铵 作用下， 以 丙酮 为溶剂， 反应 0.33h， 以100%的产率得到3-bromo-5-chloro-4H-1,2,6-thiadiazin-4-one
  参考文献：
  名称：

  Selective Stille Coupling Reactions of 3-Chloro-5-halo(pseudohalo)-4H-1,2,6-thiadiazin-4-ones

  摘要：

  A series of 3-chloro-5-halo(pseudohalo)-4H-1,2,6-thiadiazin-4-ones (halo/pseudohalo = Br, I, OTf) are prepared from 3,5-dichloro-4H-1,2,6-thiadiazin-4-one (3) in good yields. Of these the triflate reacts with tributyltin arenes (Stille couplings) chemoselectively to give only the 5-aryl-3-chloro-4H-1,2,6-thiadiazin-4-ones in high yields. This allowed the preparation of a series of unsymmetrical biaryl thiadiazines and ultimately a series of oligomers. Furthermore, treatment of 3-chloro-5-iodo-4H-1,2,6-thiadiazin-4-one (10) with Bu3SnH and Pd(OAc)(2) gave the bithiadiazinone which can also be further arylated via the Stille reaction to give bisthien-2-yl and bis(N-methylpyrrol-2-yl) analogs.

  DOI：

  10.1021/ol2025235
• 作为产物：
  描述：

  三氟甲磺酸酐 、 3-chloro-5-hydroxy-4H-1,2,6-thiadiazin-4-one 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以78%的产率得到3-chloro-5-trifluoromethanesulfonoxy-4H-1,2,6-thiadiazin-4-one
  参考文献：
  名称：

  Selective Stille Coupling Reactions of 3-Chloro-5-halo(pseudohalo)-4H-1,2,6-thiadiazin-4-ones

  摘要：

  A series of 3-chloro-5-halo(pseudohalo)-4H-1,2,6-thiadiazin-4-ones (halo/pseudohalo = Br, I, OTf) are prepared from 3,5-dichloro-4H-1,2,6-thiadiazin-4-one (3) in good yields. Of these the triflate reacts with tributyltin arenes (Stille couplings) chemoselectively to give only the 5-aryl-3-chloro-4H-1,2,6-thiadiazin-4-ones in high yields. This allowed the preparation of a series of unsymmetrical biaryl thiadiazines and ultimately a series of oligomers. Furthermore, treatment of 3-chloro-5-iodo-4H-1,2,6-thiadiazin-4-one (10) with Bu3SnH and Pd(OAc)(2) gave the bithiadiazinone which can also be further arylated via the Stille reaction to give bisthien-2-yl and bis(N-methylpyrrol-2-yl) analogs.

  DOI：

  10.1021/ol2025235

文献信息

• Selective Stille Coupling Reactions of 3-Chloro-5-halo(pseudohalo)-4<i>H</i>-1,2,6-thiadiazin-4-ones
  作者：Heraklidia A. Ioannidou、Christos Kizas、Panayiotis A. Koutentis

  DOI：10.1021/ol2025235

  日期：2011.11.4

  A series of 3-chloro-5-halo(pseudohalo)-4H-1,2,6-thiadiazin-4-ones (halo/pseudohalo = Br, I, OTf) are prepared from 3,5-dichloro-4H-1,2,6-thiadiazin-4-one (3) in good yields. Of these the triflate reacts with tributyltin arenes (Stille couplings) chemoselectively to give only the 5-aryl-3-chloro-4H-1,2,6-thiadiazin-4-ones in high yields. This allowed the preparation of a series of unsymmetrical biaryl thiadiazines and ultimately a series of oligomers. Furthermore, treatment of 3-chloro-5-iodo-4H-1,2,6-thiadiazin-4-one (10) with Bu3SnH and Pd(OAc)(2) gave the bithiadiazinone which can also be further arylated via the Stille reaction to give bisthien-2-yl and bis(N-methylpyrrol-2-yl) analogs.