2-Fluor-benzol-1-sulfonsaeure-anilid | 30058-41-4

• 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: 2-Fluor-benzol-1-sulfonsaeure-anilid
• 英文别名: 2-fluoro-N-phenylbenzenesulfonamide
• CAS: 30058-41-4
• 化学式: C₁₂H₁₀FNO₂S
• 分子量: 251.281
• InChiKey: OGUKCHSGOJXRND-UHFFFAOYSA-N

物化性质

• 沸点：
  383.2±44.0 °C(Predicted)
• 密度：
  1.374±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Fluor-benzol-1-sulfonsaeure-anilid 在 palladium 10% on activated carbon 、 氢气 、 sodium hydride 、 potassium carbonate 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 (R*)-4-((S*)-2,3-dihydrobenzofuran-2-yl)-2-phenyl-3,4-dihydro-2H-benzo[b][1,4,5]oxathiazepine 1,1-dioxide
  参考文献：
  名称：

  Construction of Benzosultam‐Containing Fused‐ and Linked‐Biheterocycles by a Cascade Double Nucleophilic Cyclization

  摘要：

  AbstractAlthough nucleophilic aromatic substitution (SNAr) and many nucleophilic epoxide ring‐opening reactions proceed under similar anionic conditions, the literature examples of using these reactions in tandem for the construction of heterocyclic compounds are scarce. In this article, we disclose a detailed account of the synthesis of benzothiaoxazepine‐1,1‐dioxide‐containing fused‐ and linked‐biheterocycles by a base‐mediated, exo‐selective intramolecular epoxide‐opening/intramolecular nucleophilic aromatic substitution cascade of epoxide‐tethered ortho‐fluorobenzenesulfonamides. A wide range of substrates exhibited high overall yields and complete regio‐ and diastereoselectivity

  DOI：

  10.1002/ejoc.202101421
• 作为产物：
  描述：

  2-氟苯磺酰氯 、 苯胺 在 吡啶 作用下， 反应 24.0h， 生成 2-Fluor-benzol-1-sulfonsaeure-anilid
  参考文献：
  名称：

  实用化学选择性芳族取代：N-苯基苯磺酰胺高效硝化卤化合成N-(4-卤代-2-硝基苯基)苯磺酰胺

  摘要：

  开发了一种金属促进的N-苯基苯磺酰胺串联硝化和卤化合成N- (4-卤代-2-硝基苯基)苯磺酰胺衍生物的新路线。该方法显示出高度实用的化学选择性和官能团兼容性。此外，它采用不敏感且廉价的Cu(NO 3 ) 2 ·3H 2 O、Fe(NO 3 ) 3 ·9H 2 O和NH 4 NO 3作为硝化试剂，为制备硝化试剂提供了直接途径。 4-卤代-2-硝基苯胺，是合成苯并咪唑和喹喔啉衍生物的重要中间体。

  DOI：

  10.1039/d2ob01028c

文献信息

• Conjugate Addition - SNAr Domino Reaction for the Synthesis of Benzo- or Pyridyl-Fused Lactams and Sultams
  作者：Karsten Juhl、Niels Nørager

  DOI：10.1055/s-0030-1258302

  日期：2010.12

  A versatile domino reaction that can be used for the synthesis of bicyclic benzo- or pyridyl-fused lactam and sultam derivatives is presented, enabling rapid synthesis of a variety of complex structures.

  提出了一种多功能多米诺反应，可用于合成双环苯或吡啶融合的内酰胺和内硫酸酯衍生物，使得多种复杂结构的快速合成成为可能。
• Pentafluorobenzenesulfonamides and analogs
  申请人：Tularik Inc.

  公开号：US20030162817A1

  公开（公告）日：2003-08-28

  The invention provides methods and compositions relating to novel pentafluorophenylsulfonamide derivatives and analogs and their use as pharmacologically active agents. The compositions find particular use as pharmacological agents in the treatment of disease states, particularly cancer, vascular restenosis, microbial infections, and psoriasis, or as lead compounds for the development of such agents. The compositions include compounds of the general formula I: 1

  本发明提供了涉及新型五氟苯磺酰胺衍生物和类似物的方法和组合物以及它们作为药理活性剂的用途。该组合物在治疗疾病状态，特别是癌症、血管再狭窄、微生物感染和牛皮癣方面，作为药理剂的特定用途，或作为这些药理剂开发的先导化合物。该组合物包括一般式I的化合物：1
• Practical chemoselective aromatic substitution: the synthesis of <i>N</i>-(4-halo-2-nitrophenyl)benzenesulfonamide through the efficient nitration and halogenation of <i>N</i>-phenylbenzenesulfonamide
  作者：Xiao Yu、Wenjing Zhu、Hongyan Liu、Yi Liu、Hongshuang Li、Junfen Han、Guiyun Duan、Zhushuang Bai、Pengfei Zhang、Chengcai Xia

  DOI：10.1039/d2ob01028c

  日期：——

  the metal-promoted tandem nitration and halogenation of N-phenylbenzenesulfonamide to synthesize N-(4-halo-2-nitrophenyl)benzenesulfonamide derivatives has been developed. The method shows highly practical chemoselective and functional group compatibility. In addition, it employs insensitive and inexpensive Cu(NO3)2·3H2O, Fe(NO3)3·9H2O, and NH4NO3 as the nitration reagents, and it provides a direct

  开发了一种金属促进的N-苯基苯磺酰胺串联硝化和卤化合成N- (4-卤代-2-硝基苯基)苯磺酰胺衍生物的新路线。该方法显示出高度实用的化学选择性和官能团兼容性。此外，它采用不敏感且廉价的Cu(NO 3 ) 2 ·3H 2 O、Fe(NO 3 ) 3 ·9H 2 O和NH 4 NO 3作为硝化试剂，为制备硝化试剂提供了直接途径。 4-卤代-2-硝基苯胺，是合成苯并咪唑和喹喔啉衍生物的重要中间体。
• Synthesis of benzimidazole-fused 1,4-benzoxazepines and benzosultams spiro-connected to a 2-oxindole core <i>via</i> a tandem epoxide-opening/S_NAr approach
  作者：Abhijit Gogoi、Subhamoy Mukhopadhyay、Raju Chouhan、Sajal Kumar Das

  DOI：10.1039/d3ob01613g

  日期：——

  s toward the synthesis of two new classes of spirooxindole-based polycyclic systems. Mechanistically, this conceptually simple and high atom-economical reaction proceeds via an SN2-like intermolecular epoxide ring-opening, accompanied by a concomitant intramolecular SNAr reaction. From a synthetic aspect, the notable features of the process are its full regioselectivity, operational simplicity using

  虽然数百篇文献报道描述了基于螺吲哚的五元和六元杂环的制备，但螺连接至2-羟吲哚核心的七元杂环的构建迄今为止开发较少。在此，我们公开了螺环环氧吲哚和2-(2-氟芳基) -1H-苯并咪唑或2-氟-N-芳基苯磺酰胺的碱介导的(4+3)环化，以合成两类新的基于螺环吲哚的化合物多环系统。从机理上讲，这种概念上简单且高原子经济性的反应通过类似 S N 2 的分子间环氧化物开环进行，并伴有伴随的分子内 S N Ar 反应。从合成方面来看，该工艺的显着特点是其完全的区域选择性、在无过渡金属条件下使用现成底物的操作简单性、高产率和广泛的底物范围。
• Construction of Benzosultam‐Containing Fused‐ and Linked‐Biheterocycles by a Cascade Double Nucleophilic Cyclization
  作者：Jonali Das、Biraj Jyoti Borah、Sajal Kumar Das

  DOI：10.1002/ejoc.202101421

  日期：2022.3.15

  AbstractAlthough nucleophilic aromatic substitution (SNAr) and many nucleophilic epoxide ring‐opening reactions proceed under similar anionic conditions, the literature examples of using these reactions in tandem for the construction of heterocyclic compounds are scarce. In this article, we disclose a detailed account of the synthesis of benzothiaoxazepine‐1,1‐dioxide‐containing fused‐ and linked‐biheterocycles by a base‐mediated, exo‐selective intramolecular epoxide‐opening/intramolecular nucleophilic aromatic substitution cascade of epoxide‐tethered ortho‐fluorobenzenesulfonamides. A wide range of substrates exhibited high overall yields and complete regio‐ and diastereoselectivity