4-methoxy-N-(oxiran-2-ylmethyl)benzenesulfonamide | 1144506-82-0

• 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: 4-methoxy-N-(oxiran-2-ylmethyl)benzenesulfonamide
• 英文别名: 4-Methoxy-N-oxiranylmethyl-benzenesulfonamide
• CAS: 1144506-82-0
• 化学式: C₁₀H₁₃NO₄S
• 分子量: 243.284
• InChiKey: PJSMWCYPHDVNPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  76.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-methoxy-N-(oxiran-2-ylmethyl)benzenesulfonamide 在 三氟化硼 、 potassium carbonate 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 9-((4-methoxyphenyl)sulfonyl)-3,4-diphenyl-2,6-dioxa-9-azabicyclo[3.2.2]non-3-ene
  参考文献：
  名称：

  环氧烯酰胺的扩环/开环反应：获得氮杂双环壬烯、四氢吡啶和四唑支架

  摘要：

  由环氧（末端和内部）苯磺酰胺和取代的氯丙烯醛获得的烯磺酰胺经过路易斯酸 (BF 3 ·OEt 2 ) 催化环化，根据底物提供氮杂双环酮、苯甲酸四氢吡啶酯或四氢吡啶甲醛支架。在Me 3 SiN 3存在下，很容易得到取代的四唑。主要产品已通过单晶 X 射线晶体学进行表征。

  DOI：

  10.1039/d3nj00529a
• 作为产物：
  描述：

  对甲氧基苯磺酰氯 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 4-methoxy-N-(oxiran-2-ylmethyl)benzenesulfonamide
  参考文献：
  名称：

  环氧酰胺和烯酰胺的扩环反应：功能化氮杂环丁烷、二氢呋喃、重氮烷或 Dioxa-3-azabicyclonon-4-enes？

  摘要：

  功能化的氮杂环丁烷、2,3-二氢呋喃或非正统的二氧杂环己烷-3-氮杂双环酮-4-烯基序是N-环氧乙烷基甲基苯磺酰胺和 β-氯-肉桂醛之间的无过渡金属反应的产物，具体取决于是否使用 NaI /K 2 CO 3或 LiBr/K 2 CO 3。这些扩环反应涉及衍生自N-环氧乙烷基甲基苯磺酰胺和 β-氯肉桂醛作为中间体的烯酰胺（X 射线证据） 。N-环氧乙烷基甲基苯磺酰胺本身在加热时产生易于分离的结晶异构重氮杂环烷，其可通过X-射线晶体学表征。

  DOI：

  10.1021/acs.joc.2c00268

文献信息

• Synthesis of thiazolidine-thiones, imino-thiazolidines and oxazolidines <i>via</i> the base promoted cyclisation of epoxy-sulfonamides and heterocumulenes
  作者：Mandala Anitha、K. C. Kumara Swamy

  DOI：10.1039/c7ob02915b

  日期：——

  Epoxy-sulfonamides react with heterocumulenes (carbon disulfide/isothiocyanates/isocyanates) in the presence of a base to afford ring expansion products in good to high yields with excellent regioselectivity. N-(2-Bromoethyl)-sulfonamides can also be employed as substrates. This reaction proceeds through a 5-exo-tet pathway without forming aziridine intermediates.

  环氧磺酰胺在碱的存在下与杂聚枯烯（二硫化碳/异硫氰酸酯/异氰酸酯）反应，以良好的收率和高收率提供极好的区域选择性的扩环产物。N-（2-溴乙基） -磺酰胺也可以用作底物。该反应通过5 -exo-tet途径进行，而没有形成氮丙啶中间体。
• Transition Metal-Free Cascade Cyclization of Epoxy-Ynamides: To Go for 1,3-Oxazines or 1,4-Oxazines?
  作者：A. Leela Siva Kumari、Alla Siva Reddy、K. C. Kumara Swamy

  DOI：10.1021/acs.orglett.6b03047

  日期：2016.11.4

  An approach to both 1,3- and 1,4-oxazines is developed by the cascade cyclization of epoxy ynamides under transition metal-free conditions. Thus, while 1,3-oxazines are obtained in a regio- and stereoselective manner by using base, cyclization of epoxy ynamides with sodium azide as a nucleophile results in 1,4-oxazines. Deuterium-labeling experiment demonstrates the role of water as a proton source in the formation of 1,4-oxazines. Epoxy tethered alkyne precursors provide 1,4-oxazines that undergo click reaction.
• Phosphorylated hydroxyethylamines as novel inhibitors of the bacterial cell wall biosynthesis enzymes MurC to MurF
  作者：Matej Sova、Andreja Kovač、Samo Turk、Martina Hrast、Didier Blanot、Stanislav Gobec

  DOI：10.1016/j.bioorg.2009.09.001

  日期：2009.12

  Enzymes involved in the biosynthesis of bacterial peptidoglycan represent important targets for development of new antibacterial drugs. Among them, Mur ligases (MurC to MurF) catalyze the formation of the final cytoplasmic precursor UDP-N-acetylmuramyl-pentapeptide from UDP-N-acetylmuramic acid. We present the design, synthesis and biological evaluation of a series of phosphorylated hydroxyethylamines as new type of small-molecule inhibitors of Mur ligases. We show that the phosphate group attached to the hydroxyl moiety of the hydroxyethylamine core is essential for good inhibitory activity. The IC50 values of these inhibitors were in the micromolar range, which makes them a promising starting point for the development of multiple inhibitors of Mur ligases as potential antibacterial agents. In addition, 1-(4-methoxyphenylsulfonamido)-3-morpholinopropan-2-yl dihydrogen phosphate 7a was discovered as one of the best inhibitors of MurE described so far. (C) 2009 Elsevier Inc. All rights reserved.
• Design and synthesis of new hydroxyethylamines as inhibitors of d-alanyl-d-lactate ligase (VanA) and d-alanyl-d-alanine ligase (DdlB)
  作者：Matej Sova、Gašper Čadež、Samo Turk、Vita Majce、Slovenko Polanc、Sarah Batson、Adrian J. Lloyd、David I. Roper、Colin W.G. Fishwick、Stanislav Gobec

  DOI：10.1016/j.bmcl.2009.01.034

  日期：2009.3

  The Van enzymes are ATP-dependant ligases responsible for resistance to vancomycin in Staphylococcus aureus and Enteroccoccus species. The de novo molecular design programme SPROUT was used in conjunction with the X-ray crystal structure of Enterococcus faecium D-alanyl-D-lactate ligase (VanA) to design new putative inhibitors based on a hydroxyethylamine template. The two best ranked structures were selected and efficient syntheses developed. The inhibitory activities of these molecules were determined on E. faecium VanA, and due to structural similarity and a common reaction mechanism, also on D-Ala-D-Ala ligase (DdlB) from Escherichia coli. The phosphate group attached to the hydroxyl moiety of the hydroxyethylamine isostere within these systems is essential for their inhibitory activity against both VanA and DdlB. (C) 2009 Elsevier Ltd. All rights reserved.