1-butanesulfonyl isocyanate | 3670-24-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: 1-butanesulfonyl isocyanate
• 英文别名: butanesulfonyl isocyanate；1-Butansulfonylisocyanat；n-Butansulfonylisocyanat；n-butylsulphonyl isocyanate；n-butylsulfonyl isocyanate；butylsulfonyl isocyanate；N-(oxomethylidene)butane-1-sulfonamide
• CAS: 3670-24-4
• 化学式: C₅H₉NO₃S
• 分子量: 163.197
• InChiKey: WAVUSALOADVQTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  72
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-butanesulfonyl isocyanate 在 水 作用下， 生成 1-丁烷磺酰胺
  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：

  O-Ethyl-N-butansulfonylcarbamat 生成 1-butanesulfonyl isocyanate
  参考文献：
  名称：

  Synthesis of alkanesulfonyl isocyanates by thermolysis of trimethylsilyated sulfonyl carbamates

  摘要：

  DOI：

  10.1021/jo00924a039

文献信息

• Reactions of Benzocyclopropene with Sulfonyl Isocyanates and Nitrones: Cycloadditions through C–C σ-Bond Rupture of Three-Membered Ring
  作者：Shinzo Kagabu、Katsuhiro Saito、Hiroyuki Watanabe、Kensuke Takahashi、Katsuaki Wada

  DOI：10.1246/bcsj.64.106

  日期：1991.1

  Alkane- and arenesulfonyl isocyanates were added to benzocyclopropene across the C–C σ-bond of the three-membered ring, giving 2-sulfonyl-1-isoindolinones. The reaction with C,N-diphenylnitrone afforded a similar cyclization product, 3,4-dihydro-3,4-diphenyl-1H-2,3-benzoxazine. These reactions are considered to proceed through zwitterionic intermediates formed by the fission of the C–C σ-bond of the

  烷烃和芳烃磺酰基异氰酸酯通过三元环的 C-C σ 键添加到苯并环丙烯中，得到 2-磺酰基-1-异吲哚啉酮。与 C,N-二苯基硝酮反应得到类似的环化产物 3,4-二氢-3,4-二苯基-1H-2,3-苯并恶嗪。这些反应被认为是通过亲电子试剂裂变三元环的 C-C σ 键形成的两性离子中间体进行的。
• N-sulfonyl carboxylic amide derivative including an N-containing
  申请人：Kumiai Chemical Industry Co., Ltd.

  公开号：US05444060A1

  公开（公告）日：1995-08-22

  The present invention provides an N-sulfonyl carboxylic amide derivative including an N-containing 6-membered aromatic ring represented by formula [I]: ##STR1## wherein R.sup.1 represents an alkyl group, an alkenyl group, or the like, R.sup.2 represents a hydrogen atom, an alkyl group, or the like, R.sup.3 and R.sup.4 represent independently an alkyl group, alkoxy group, or the like, and X and Y represent independently a methyne group or a nitrogen atom; or the salt of the same, a method for producing the same, and a biocide containing the same as an active ingredient. The N-sulfonyl carboxylic amide derivative including an N-containing 6-membered aromatic ring according to the present invention exhibits superior effects against blight caused by plant pathogenic fungi belonging to Oomycetes such as downy mildew, late blight, or the like in a low concentration as well as controls weeds occurring in paddy fields and plowed fields.

  本发明提供了一种N-磺酰基羧酰胺衍生物，其中包括由公式[I]表示的含N的6元芳香环： ##STR1## 其中，R.sup.1表示烷基、烯基或类似物，R.sup.2表示氢原子、烷基或类似物，R.sup.3和R.sup.4独立地表示烷基、烷氧基或类似物，X和Y独立地表示亚甲基或氮原子；或其盐，以及制备该衍生物的方法和含有该衍生物作为活性成分的杀菌剂。本发明提供的包括N-磺酰基羧酰胺衍生物的含N的6元芳香环在低浓度下对属于Oomycetes的植物病原真菌引起的病害，如霜霉病、晚疫病等，表现出卓越的效果，并控制出现在稻田和犁地中的杂草。
• Kagabu, Shinzo; Inoue, Tatsuo, Chemistry Letters, 1989, p. 2181 - 2182
  作者：Kagabu, Shinzo、Inoue, Tatsuo

  DOI：——

  日期：——
• Synthesis and structure-activity relationship study of pyrrolidine-oxadiazoles as anthelmintics against Haemonchus contortus
  作者：Banfeng Ruan、Yuezhou Zhang、Solomon Tadesse、Sarah Preston、Aya C. Taki、Abdul Jabbar、Andreas Hofmann、Yaqing Jiao、Jose Garcia-Bustos、Jitendra Harjani、Thuy Giang Le、Swapna Varghese、Silvia Teguh、Yiyue Xie、Jephthah Odiba、Min Hu、Robin B. Gasser、Jonathan Baell

  DOI：10.1016/j.ejmech.2020.112100

  日期：2020.3

  Parasitic roundworms (nematodes) are significant pathogens of humans and animals and cause substantive socioeconomic losses due to the diseases that they cause. The control of nematodes in livestock animals relies heavily on the use of anthelmintic drugs. However, their extensive use has led to a widespread problem of drug resistance in these worms. Thus, the discovery and development of novel chemical entities for the treatment of parasitic worms of humans and animals is needed. Herein, we describe our medicinal chemistry optimization efforts of a phenotypic hit against Haemonchus contortus based on a pyrrolidine-oxadiazole scaffold. This led to the identification of compounds with potent inhibitory activities (IC50 = 0.78-22.4 mu M) on the motility and development of parasitic stages of H. contortus, and which were found to be highly selective in a mammalian cell counter-screen. These compounds could be used as suitable chemical tools for drug target identification or as lead compounds for further optimization. (C) 2020 Elsevier Masson SAS. All rights reserved.
• KAGABU, SHINZO;INOUE, TATSUO, CHEM. LETT.,(1989) N2, C. 2181-2182
  作者：KAGABU, SHINZO、INOUE, TATSUO

  DOI：——

  日期：——