thiophen-2-yl-sulfonyl isocyanate | 64902-33-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: thiophen-2-yl-sulfonyl isocyanate
• 英文别名: thiophene-2-sulfonyl isocyanate；thiophenesulfonyl isocyanate；2-thiophenesulfonyl isocyanate；N-(oxomethylidene)thiophene-2-sulfonamide
• CAS: 64902-33-6
• 化学式: C₅H₃NO₃S₂
• mdl: MFCD00792665
• 分子量: 189.216
• InChiKey: JBPHCEHVHVSGEP-UHFFFAOYSA-N

物化性质

• 沸点：
  285.0±13.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  thiophen-2-yl-sulfonyl isocyanate 在 水 作用下， 生成 2-噻吩磺酰胺
  参考文献：
  名称：

  Tin for organic synthesis. 10. Unconventional regiospecific syntheses of aromatic carbonamides and thiocarbonamides by means of tin-mediated Friedel-Crafts reactions

  摘要：

  Friedel-Crafts reactions of stannylarenes 1 with tosyl isocyanate (TsNCO, 2) give N-tosylcarbonamides 3 via ipso substitution of the stannyl group. Thus, unconventionally substituted aromatic carbonamides can be obtained. The combination of the reaction of 1 and 2 with that of 1 and chlorosulfonyl isocyanate (14) allows one-pot syntheses of N-(arylsulfonyl)-substituted aromatic carbonamides with optional substitution patterns on both aromatic rings. The known ipso-specific substitutions of stannylarenes with 14 are extended to bi- and tricyclic arenes as well as to thiophenes 6 and 22. One stannyl group can serve as a leaving group for two aromatic systems, as shown with diaryldialkyltins 29. Also, stannylalkanes such as 27 react with 14 to afford alkylsulfonyl isocyanates and products of further reactions, such as 28. From the reactions of 1 with ethoxycarbonyl isothiocyanate (32), ortho- and meta-substituted aromatic thiocarbonamides 33 which are potential precursors for further syntheses, are accessible. The scope, limitations, and mechanism of these electrophilic substitutions are outlined.

  DOI：

  10.1021/jo00077a020
• 作为产物：
  描述：

  N-[(1-oxo-2-oxo-2-chloro)ethyl]-(2-thiophene)sulfonamide 、 邻二氯苯 以30%的产率得到thiophen-2-yl-sulfonyl isocyanate
  参考文献：
  名称：

  NMDA antagonists

  摘要：

  本发明涉及一类新的4-磺胺基喹啉衍生物，以及它们作为NMDA拮抗剂的用途。

  公开号：

  US05606063A1

文献信息

• Herbicidal sulfonamides
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US04190432A1

  公开（公告）日：1980-02-26

  N-(heterocyclicaminocarbonyl)arylsulfonamides, such as N-[(4-methoxy-6-methylamino-1,3,5-triazin-2-yl)-aminocarbonyl]benzenesulfo namide, are useful for the regulation of plant growth and as herbicides, particularly for controlling volunteer corn in soybeans.

  N-(杂环氨基甲酰基)芳基磺酰胺，例如N-[(4-甲氧基-6-甲氨基-1,3,5-三嗪-2-基)-氨基甲酰基]苯磺酰胺，对于植物生长的调节和作为除草剂是有用的，特别是用于控制大豆中的自愿玉米。
• Carboxylic acids and acylsulfonamides, compositions containing such compounds and methods of treatment
  申请人：Merck Frosst Canada & Co.

  公开号：US06242493B1

  公开（公告）日：2001-06-05

  Compounds of formula I: as well as pharmaceutically acceptable salts, hydrates and esters thereof, are disclosed. The compounds are useful for treating or preventing prostaglandin mediated diseases. Pharmaceutical compositions containing such compounds and methods of treatment are also included.

  公式I的化合物，以及其药学上可接受的盐、水合物和酯被揭示出来。这些化合物可用于治疗或预防前列腺素介导的疾病。还包括含有这些化合物的药物组合物和治疗方法。
• Herbicidal pyrimidine and triazine sulfonamides
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US04214890A1

  公开（公告）日：1980-07-29

  N-(heterocyclicaminocarbonyl)arylsulfonamides and thienylsulfonamides in which the heterocyclic radical is substituted in one position by a methyl or methoxy radical and in another by a substituted alkoxy or alkylthio radical; e.g., N-[[4-(2-methoxyethoxy)-6-methylpyrimidin-2-yl]aminocarbonyl]-2-nitrobenze nesulfonamide and N-[[4-(2,2,2-trifluoroethoxy)-6-methylpyrimidin-2-yl]aminocarbonyl]-2-nitr obenzenesulfonamide; are useful for the regulation of plant growth and as pre-emergence and post-emergence herbicides.

  N-(杂环氨基甲酰)芳基磺酰胺和噻吩磺酰胺，其中杂环基在一个位置被甲基或甲氧基基团取代，在另一个位置被取代的烷氧基或烷硫基基团取代；例如，N-[[4-(2-甲氧基乙氧基)-6-甲基嘧啶-2-基]氨基甲酰]-2-硝基苯磺酰胺和N-[[4-(2,2,2-三氟乙氧基)-6-甲基嘧啶-2-基]氨基甲酰]-2-硝基苯磺酰胺；可用于植物生长的调节以及作为除草剂的预发芽和后发芽。
• Herbicidal triazine sulfonamides
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US04501607A1

  公开（公告）日：1985-02-26

  N-(heterocyclicaminocarbonyl)arylsulfonamides and thienylsulfonamides in which the heterocyclic radical is disubstituted; e.g., N-[[4-(2-methoxyethoxy)-6-methylpyrimidin-2-yl]aminocarbonyl]-2-nitrobenze nesulfonamide and N-[[(4-(2,2,2-trifluoroethoxy)-6-methylpyrimidin-2-yl]aminocarbonyl]-2-nit robenzenesulfonamide; are useful for the regulation of plant growth and as pre-emergence and post-emergence herbicides.

  N-（杂环氨基甲酰基）芳基磺酰胺和噻吩磺酰胺，其中杂环基团是二取代的;例如，N-[[4-（2-甲氧基乙氧基）-6-甲基嘧啶-2-基]氨基甲酰基]-2-硝基苯磺酰胺和N-[[(4-（2,2,2-三氟乙氧基）-6-甲基嘧啶-2-基]氨基甲酰基]-2-硝基苯磺酰胺; 对于植物生长的调节以及作为预防出苗和后出苗除草剂是有用的。
• Agriculture sulfonamides
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US04684395A1

  公开（公告）日：1987-08-04

  N-(heterocyclicaminocarbonyl)arylsulfonamides and thienylsulfonamides in which the heterocyclic radical is disubstituted; e.g., N-[[4-(2-methoxyethyoxy)-6-methylpyrimidin-2-yl]aminocarbonyl]-2-nitrobenz enesulfonamide and N-[[4-(2,2,2-trifluoroethoxy)-6-methylpyrimidin-2-yl]aminocarbonyl]-2-nitr obenzenesulfonamide; are useful for the regulation of plant growth and as pre-emergence and post-emergence herbicides.

  N-（杂环氨基甲酰基）芳基磺酰胺和噻吩磺酰胺，其中杂环基团是二取代的；例如，N-[[4-（2-甲氧基乙氧基）-6-甲基嘧啶-2-基]氨基甲酰基]-2-硝基苯磺酰胺和N-[[4-（2,2,2-三氟乙氧基）-6-甲基嘧啶-2-基]氨基甲酰基]-2-硝基苯磺酰胺；可用于调节植物生长和作为除草剂的前期和后期应用。