N-fluorosulfonyl-benzotriazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: N-fluorosulfonyl-benzotriazole
• 英文别名: 1H-1,2,3-benzotriazole-1-sulfonyl fluoride；benzotriazole-1-sulfonyl fluoride
• 化学式: C₆H₄FN₃O₂S
• 分子量: 201.181
• InChiKey: FCEHRHQASKIZPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  T406石油添加剂 在 PEG-400 、 sodium hydroxide 、 N,N-二氟-O-氟磺酰羟胺 作用下， 以 水 、 乙二醇 、 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以32%的产率得到N-fluorosulfonyl-benzotriazole
  参考文献：
  名称：

  Reaction of NH-azoles with O-fluorosulfonyl-N,N-difluorohydroxylamine. Synthesis of N-fluorosulfonylazoles

  摘要：

  O-Fluorosulfonyl-N,N-difluorohydroxylamine (FH) reacts with anions of NH-azoles (imidazoles, pyrazoles, and 1,2,3-triazoles) to give the corresponding N-fluorosulfonylazoles, which were used to obtain N,N'-sulfonylbisazoles. The N-fluorosulfonylation proceeds at the nitrogen atom furthest from the most electron-withdrawing substituent in the azole ring. Nonaromatic NH-acid anions (imides and primary N-nitroamines) are sometimes capable of giving N-fluorosulfonyl derivatives although in yields less than 5 %. These products are much less stable than N-fluorosulfonylazoles. The N-fluorosulfonylation presumably proceeds as nucleophilic substitution at the sulfur atom of FH.

  DOI：

  10.1007/bf00863829

文献信息

• Sulfonyldiazoles and N-(fluorosulfonyl)azoles, and methods of making the same
  申请人：Trinapco, Inc.

  公开号：US11014945B2

  公开（公告）日：2021-05-25

  The present disclosure provides methods for producing N-(fluorosulfonyl)azoles, sulfonyldiazoles, or related derivatives thereof; and the related products including N-(fluorosulfonyl)azoles, sulfonyldiazoles, and related derivatives thereof. For example, an N-(fluorosulfonyl)azole is obtained by reaction of sulfuryl fluoride with an azoles, an azole anion compound, a silylazole, or a combination thereof. Symmetric and asymmetric sulfonyldiazoles are obtained by further reaction of such an N-(fluorosulfonyl)azole with azoles, azole anion compounds, or silylazoles. A sulfonyldiazole can be also produced by reacting sulfuryl fluoride with an azole, a silylazole, or a combination thereof in one pot.

  本公开提供了生产N-(氟磺酰基)唑、磺酰基噻唑或其相关衍生物的方法；以及包括N-(氟磺酰基)唑、磺酰基噻唑和其相关衍生物在内的相关产品。例如，N-(氟磺酰基)唑是通过氟化硫与唑类化合物、唑阴离子化合物、水飞唑或它们的组合反应而得到的。通过这种 N-(氟磺酰基)唑与唑类化合物、唑阴离子化合物或硅唑的进一步反应，可得到对称和不对称磺酰二唑。磺酰基二唑也可以通过将硫酰氟与唑、水飞唑或它们的混合物在一个锅中反应制得。
• SULFONYLDIAZOLES AND N-(FLUOROSULFONYL)AZOLES, AND METHODS OF MAKING THE SAME
  申请人：Trinapco, Inc

  公开号：EP3953336A2

  公开（公告）日：2022-02-16
• [EN] SULFONYLDIAZOLES AND N-(FLUOROSULFONYL)AZOLES, AND METHODS OF MAKING THE SAME<br/>[FR] SULFONYLDIAZOLES ET N-(FLUOROSULFONYL)AZOLES, ET LEURS PROCÉDÉS DE PRÉPARATION
  申请人：TRINAPCO INC

  公开号：WO2020210174A2

  公开（公告）日：2020-10-15

  The present disclosure provides methods for producing N-(fluorosulfonyl)azoles, sulfonyldiazoles, or related derivatives thereof; and the related products including N- (fluorosulfonyl)azoles, sulfonyldiazoles, and related derivatives thereof. For example, an N- (fluorosulfonyl)azole is obtained by reaction of sulfuryl fluoride with an azoles, an azole anion compound, a silylazole, or a combination thereof. Symmetric and asymmetric sulfonyldiazoles are obtained by further reaction of such an N-(fluorosulfonyl)azole with azoles, azole anion compounds, or silylazoles. A sulfonyldiazole can be also produced by reacting sulfuryl fluoride with an azole, a silylazole, or a combination thereof in one pot.
• Reaction of NH-azoles with O-fluorosulfonyl-N,N-difluorohydroxylamine. Synthesis of N-fluorosulfonylazoles
  作者：S. A. Shevelev、V. M. Vinogradov、I. L. Dalinger、B. I. Ugrak、A. A. Fainzilberg、V. I. Fillipov

  DOI：10.1007/bf00863829

  日期：1992.10

  O-Fluorosulfonyl-N,N-difluorohydroxylamine (FH) reacts with anions of NH-azoles (imidazoles, pyrazoles, and 1,2,3-triazoles) to give the corresponding N-fluorosulfonylazoles, which were used to obtain N,N'-sulfonylbisazoles. The N-fluorosulfonylation proceeds at the nitrogen atom furthest from the most electron-withdrawing substituent in the azole ring. Nonaromatic NH-acid anions (imides and primary N-nitroamines) are sometimes capable of giving N-fluorosulfonyl derivatives although in yields less than 5 %. These products are much less stable than N-fluorosulfonylazoles. The N-fluorosulfonylation presumably proceeds as nucleophilic substitution at the sulfur atom of FH.

表征谱图