N-chloro-N-methylbenzenesulfonamide | 25997-37-9

• 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: N-chloro-N-methylbenzenesulfonamide
• 英文别名: N-chloro-N-methyl-benzenesulfonamide；N-Chlor-N-methyl-benzolsulfonamid；N-Chlor-N-methyl-benzolsulfonamid；N-Chlor-N-methylbenzolsulfonamid；N-chloro p-methyl benzenesulfonamide
• CAS: 25997-37-9
• 化学式: C₇H₈ClNO₂S
• 分子量: 205.665
• InChiKey: BRVFKIUBADNTRO-UHFFFAOYSA-N

物化性质

• 沸点：
  300.9±25.0 °C(Predicted)
• 密度：
  1.372±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-chloro-N-methylbenzenesulfonamide 、 tin(ll) chloride 以 further solvent(s) 为溶剂， 以87%的产率得到trichloro(N-methylbenzenesulfonamido)stannane
  参考文献：
  名称：

  Khmaruk, A. M.; Povolotskii, M. I.; Pinchuk, A. M., Journal of general chemistry of the USSR, 1980, vol. 50, p. 509 - 514

  摘要：

  DOI：
• 作为产物：
  描述：

  N-甲基苯磺酰胺 在 sodium hypochlorite 、 溶剂黄146 、 叔丁醇 作用下， 以 水 、 乙酸乙酯 为溶剂， 以90%的产率得到N-chloro-N-methylbenzenesulfonamide
  参考文献：
  名称：

  不使用外部催化剂的烯烃光化学氨氯化反应

  摘要：

  烯烃的光化学氨氯化：适当调整照射波长可实现烯烃氨氯化的温和光化学方案，无需外部光催化剂或使用更不稳定的 N−I 或 N−Br 起始材料进行 1, 2-氨基卤化反应。

  DOI：

  10.1002/chem.202301268

文献信息

• Visible-light-promoted chloramination of olefins with N-chlorosulfonamide as both nitrogen and chlorine sources
  作者：Qixue Qin、Daan Ren、Shouyun Yu

  DOI：10.1039/c5ob01725d

  日期：——

  A visible-light-promoted chloramination of olefins is reported.

  一种可见光促进的烯烃氯胺化反应被报道。
• Palau’chlor: A Practical and Reactive Chlorinating Reagent
  作者：Rodrigo A. Rodriguez、Chung-Mao Pan、Yuki Yabe、Yu Kawamata、Martin D. Eastgate、Phil S. Baran

  DOI：10.1021/ja5031744

  日期：2014.5.14

  Unlike its other halogen atom siblings, the utility of chlorinated arenes and (hetero)arenes are twofold: they are useful in tuning electronic structure as well as acting as points for diversification via cross-coupling. Herein we report the invention of a new guanidine-based chlorinating reagent, CBMG or "Palau'chlor", inspired by a key chlorospirocyclization en route to pyrrole imidazole alkaloids. This direct, mild, operationally simple, and safe chlorinating method is compatible with a range of nitrogen-containing heterocycles as well as select classes of arenes, conjugated pi-systems, sulfonamides, and silyl enol ethers. Comparisons with other known chlorinating reagents revealed CBMG to be the premier reagent.
• Chattaway, Journal of the Chemical Society, 1905, vol. 87, p. 159
  作者：Chattaway

  DOI：——

  日期：——
• Axinellamines as Broad-Spectrum Antibacterial Agents: Scalable Synthesis and Biology
  作者：Rodrigo A. Rodriguez、Danielle Barrios Steed、Yu Kawamata、Shun Su、Peter A. Smith、Tyler C. Steed、Floyd E. Romesberg、Phil S. Baran

  DOI：10.1021/ja508632y

  日期：2014.10.29

  Antibiotic-resistant bacteria present an ongoing challenge to both chemists and biologists as they seek novel compounds and modes of action to out-maneuver continually evolving resistance pathways, especially against Gram-negative strains. The dimeric pyrrole-imidazole alkaloids represent a unique marine natural product class with diverse primary biological activity and chemical architecture. This full account traces the strategy used to develop a second-generation route to key spirocycle 9, culminating in a practical synthesis of the axinellamines and enabling their discovery as broad-spectrum antibacterial agents, with promising activity against both Gram-positive and Gram-negative bacteria. While their detailed mode of antibacterial action remains unclear, the axinellamines appear to cause secondary membrane destabilization and impart an aberrant cellular morphology consistent with the inhibition of normal septum formation. This study serves as a rare example of a natural product initially reported to be devoid of biological activity surfacing as an active antibacterial agent with an intriguing mode of action.
• SELECTIVE CATALYTIC PROCESS FOR PREPARING N-HALOTHIOSULFONAMIDE MODIFIED TERPOLYMERS AND CATALYSTS THEREFOR
  申请人：EXXON CHEMICAL PATENTS INC.

  公开号：EP0403604A1

  公开（公告）日：1990-12-27