N-氟-o-苯二磺酰亚胺 | 134414-80-5

• 分子结构分类: 有机化合物 - 苯类化合物
• 中文名称: N-氟-o-苯二磺酰亚胺
• 英文名称: N-Fluoro-o-benzenedisulfonimide
• 英文别名: N-fluorobenzenesulfonimide；2-fluoro-1λ6,3λ6,2-benzodithiazole 1,1,3,3-tetraoxide
• CAS: 134414-80-5
• 化学式: C₆H₄FNO₄S₂
• 分子量: 237.232
• InChiKey: ILXAULYORNMOAX-UHFFFAOYSA-N

物化性质

• 沸点：
  439.5±28.0 °C(Predicted)
• 密度：
  1.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenylmagnesium bromide 、 N-氟-o-苯二磺酰亚胺 反应 0.08h， 以80%的产率得到氟苯
  参考文献：
  名称：

  N-氟-邻苯二磺酰亚胺：一种有用的新型氟化试剂

  摘要：

  N-氟-邻-苯二磺酰亚胺（5）是一种稳定，易于制备的高效“亲电子”氟源，该氟以良好的产率氟化了烯醇化物，氮杂烯化物和碳负离子。

  DOI：

  10.1016/s0040-4039(00)74290-0
• 作为产物：
  描述：

  1,2-苯二磺酰二氯 在 氨 、 fluorine 、 sodium fluoride 作用下， 以 乙醇 、 氯仿 、 一氟三氯甲烷 、 苯 为溶剂， 反应 2.0h， 生成 N-氟-o-苯二磺酰亚胺
  参考文献：
  名称：

  Selective, Electrophilic Fluorinations Using N-Fluoro-o-benzenedisulfonimide

  摘要：

  The synthesis of N-fluoro-o-benzenedisulfonimide (NFOBS, 2) and its use as an ''electrophilic'' fluorinating reagent with nucleophilic substrates is described and compared with that of N-fluorobenzenesulfonimide (NFSi, 3). NFOBS (2) is prepared in three steps in 81% overall yield from commercially available o-benzenedisulfonic acid (4) and involves treatment of o-benzenedisulfonimide (6) with dilute fluorine (10% F-2/N-2). Reaction of 2 with metal enolates, silyl enol ethers, and 1,3-dicarbonyl compounds affords the corresponding alpha-fluoro compounds in yields up to 95%, with good control of mono- and difluorination. Fluorination of ortho-metalated aromatic compounds was achieved in modest to good yields (10-80%). While the reactivities of 2 and 3 are similar, better yields were observed with the former reagent in the fluorination of metal enolates, Grignard and lithium reagents, while 3 gave better results with the ortho-lithiated aromatic substrates. The available evidence suggests an S(N)2-type mechanism for the fluorination of nucleophilic substrates by these reagents.

  DOI：

  10.1021/jo00120a014
• 作为试剂：
  描述：

  二苯甲酰基甲烷 在 N-氟-o-苯二磺酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以52%的产率得到2-fluoro-1,3-diphenyl-1,3-propanedione
  参考文献：
  名称：

  Selective, Electrophilic Fluorinations Using N-Fluoro-o-benzenedisulfonimide

  摘要：

  The synthesis of N-fluoro-o-benzenedisulfonimide (NFOBS, 2) and its use as an ''electrophilic'' fluorinating reagent with nucleophilic substrates is described and compared with that of N-fluorobenzenesulfonimide (NFSi, 3). NFOBS (2) is prepared in three steps in 81% overall yield from commercially available o-benzenedisulfonic acid (4) and involves treatment of o-benzenedisulfonimide (6) with dilute fluorine (10% F-2/N-2). Reaction of 2 with metal enolates, silyl enol ethers, and 1,3-dicarbonyl compounds affords the corresponding alpha-fluoro compounds in yields up to 95%, with good control of mono- and difluorination. Fluorination of ortho-metalated aromatic compounds was achieved in modest to good yields (10-80%). While the reactivities of 2 and 3 are similar, better yields were observed with the former reagent in the fluorination of metal enolates, Grignard and lithium reagents, while 3 gave better results with the ortho-lithiated aromatic substrates. The available evidence suggests an S(N)2-type mechanism for the fluorination of nucleophilic substrates by these reagents.

  DOI：

  10.1021/jo00120a014

文献信息

• Snieckus Victor, Beaulieu Francis, Mohri Kunihiko, Han Wei, Murphy Christ+, Tetrahedron Lett, 35 (1994) N 21, S 3465- 3468
  作者：Snieckus Victor, Beaulieu Francis, Mohri Kunihiko, Han Wei, Murphy Christ+

  DOI：——

  日期：——
• Selective, Electrophilic Fluorinations Using N-Fluoro-o-benzenedisulfonimide
  作者：Franklin A. Davis、Wei Han、Christopher K. Murphy

  DOI：10.1021/jo00120a014

  日期：1995.7

  The synthesis of N-fluoro-o-benzenedisulfonimide (NFOBS, 2) and its use as an ''electrophilic'' fluorinating reagent with nucleophilic substrates is described and compared with that of N-fluorobenzenesulfonimide (NFSi, 3). NFOBS (2) is prepared in three steps in 81% overall yield from commercially available o-benzenedisulfonic acid (4) and involves treatment of o-benzenedisulfonimide (6) with dilute fluorine (10% F-2/N-2). Reaction of 2 with metal enolates, silyl enol ethers, and 1,3-dicarbonyl compounds affords the corresponding alpha-fluoro compounds in yields up to 95%, with good control of mono- and difluorination. Fluorination of ortho-metalated aromatic compounds was achieved in modest to good yields (10-80%). While the reactivities of 2 and 3 are similar, better yields were observed with the former reagent in the fluorination of metal enolates, Grignard and lithium reagents, while 3 gave better results with the ortho-lithiated aromatic substrates. The available evidence suggests an S(N)2-type mechanism for the fluorination of nucleophilic substrates by these reagents.
• N-fluoro-o-benzenedisulfonimide: a useful new fluorinating reagent
  作者：Franklin A. Davis、Wei Han

  DOI：10.1016/s0040-4039(00)74290-0

  日期：1991.3

  N-Fluoro-o-benzenedisulfonimide (5) is a stable, easily prepared, highly efficient source of “electrophilic” fluorine which fluorinates enolates, azaenolates and carbanions in good to excellent yields.

  N-氟-邻-苯二磺酰亚胺（5）是一种稳定，易于制备的高效“亲电子”氟源，该氟以良好的产率氟化了烯醇化物，氮杂烯化物和碳负离子。