Benzol-(N-carbethoxy)-imino-sulfonsaeurechlorid | 18506-87-1

• 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: Benzol-(N-carbethoxy)-imino-sulfonsaeurechlorid
• 英文别名: Benzol--imino-sulfonsaeurechlorid；Benzolsulfonsaeure-chlorid-aethoxycarbonylimid
• CAS: 18506-87-1
• 化学式: C₉H₁₀ClNO₃S
• 分子量: 247.702
• InChiKey: BTVRUVBXZJYGSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  55.73
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Benzol-(N-carbethoxy)-imino-sulfonsaeurechlorid 在 N-溴代丁二酰亚胺(NBS) 、 sodium ethanolate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 23.5h， 生成
  参考文献：
  名称：

  N-Trifluoromethylthiolated Sulfonimidamides and Sulfoximines: Anti-microbial, Anti-mycobacterial, and Cytotoxic Activity

  摘要：

  Herein we demonstrate the expanded utility of a recently described N-trifluoromethylthiolation protocol to sulfonimidamide containing substances. The novel N-trifluoromethylthio sulfonimidamide derivatives thus obtained were evaluated for antibacterial activity against Mycobacterium tuberculosis (M. tb.) and Mycobacterium abscessus and Gram + Ve (Streptococcus aureus, Bacillus subtilis), and Gram - Ve (Escherichia coli, Pseudomonas aeruginosa) bacteria. Two compounds, 13 and 15 showed high antimycobacterial activity with MIC value of 4-8 mu g/mL; i.e. comparable to WHO recommended first line antibiotic for TB infection ethambutol. The same compounds were also found to be cytotoxic in HepG2 cells (compound 13 IC50 = 15 mu g/mL; compound 15 IC50 = 65 mu g/mL). A structure activity relationship, using matched pair analysis, gave the unexpected conclusion that the trifluoromethylthio moiety was responsible for the cellular and bacterial toxicity. Given the increasing use of the trifluoromethylthio group in contemporary medicinal chemistry, this observation calls for considerations before implementation of the functionality in drug design.

  DOI：

  10.1021/acsmedchemlett.9b00285
• 作为产物：
  描述：

  苯亚磺酰氯 在 N-氯代丁二酰亚胺 、 正丁基锂 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 4.16h， 生成 Benzol-(N-carbethoxy)-imino-sulfonsaeurechlorid
  参考文献：
  名称：

  Synthesis and arylation of unprotected sulfonimidamides

  摘要：

  Herein we evaluate different methodologies for the synthesis of unprotected sulfonimidamides. Three different procedures that allow orthogonal deprotection of the imine nitrogen under acidic, nucleophilic, and basic conditions were established. Moreover, we present a highly efficient methodology for functionalization of the imine nitrogen through Pd-catalyzed C-N arylation. RuPhos ligand was shown to allow short reaction time, excellent yields, and allowed coupling of both aryl halides and heteroaryl bromides. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.072

文献信息

• Direct Synthesis of <i>N</i> -Acyl Sulfonimidamides and <i>N</i> -Sulfonimidoyl Amidines from Sulfonimidoyl Azides
  作者：Ganesh Chandra Nandi、Irfana Jesin

  DOI：10.1002/adsc.201800215

  日期：2018.7.4

  demonstrate their utility in the construction of N‐acyl sulfonimidamides and N‐sulfonimidoyl amidines. N‐Acyl sulfonimidamides were synthesized in good to very good yields via “on water” copper‐catalyzed three‐component coupling between sulfonimidoyl azide, alkynes and water. The use of amines as nucleophiles yielded a wide range of N‐sulfonimidoyl amidines. Both reactions were completed in very short

  在这里，我们描述了磺酰亚胺基叠氮化物的制备，并证明了它们在N酰基磺酰亚胺酰胺和N磺酰亚胺基am的构建中的效用。N-酰基磺酰亚胺酰胺是通过磺酰亚胺基叠氮化物，炔烃和水之间的“水上”铜催化的三组分偶联以良好至非常高的产率合成的。使用胺作为亲核试剂可产生各种N-磺酰亚胺基yl。两种反应均在室温下于很短的条件下在很短的时间内完成，因此确立了磺酰亚胺基叠氮化物（磺酰叠氮基的氮杂类似物）的潜力，它是一步合成官能化磺酰胺基酰胺的极好前体。
• Levchenko,E.S. et al., Journal of general chemistry of the USSR, 1961, vol. 31, p. 2218 - 2222
  作者：Levchenko,E.S. et al.

  DOI：——

  日期：——