N-(4-bromophenyl)-N-methyl-benzenesulfonamide | 72385-31-0

• 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: N-(4-bromophenyl)-N-methyl-benzenesulfonamide
• 英文别名: N-(4-bromophenyl)-N-methylbenzenesulfonamide；N-(4-bromophenyl)-N-methylbenzenesulfonamide
• CAS: 72385-31-0
• 化学式: C₁₃H₁₂BrNO₂S
• 分子量: 326.214
• InChiKey: JKLMAGGEABBUOO-UHFFFAOYSA-N

物化性质

• 沸点：
  437.4±47.0 °C(Predicted)
• 密度：
  1.529±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  N-(4-bromophenyl)-N-methyl-benzenesulfonamide 在 manganese(IV) oxide 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.92h， 生成 N-methyl-N-[4-(pyridine-3-carbonyl)phenyl]benzenesulfonamide
  参考文献：
  名称：

  Stereoselectivity in the Wittig Reaction of Aromatic Ketones: Origin of Preference for the Olefin Geometry

  摘要：

  Investigation of the stereoselectivity observed in the Wittig reaction of aromatic ketones with ''nonstabilized'' phosphonium ylides revealed that the nature of the substituent on the phenyl ring of phenyl S-pyridyl ketone determined the stereoselectivity. Generally the Wittig reaction of such ketones with carboxy phosphonium ylides proceeded preferentially to yield (Z)-olefin, albeit with modest selectivity. However, the reaction with aryl sulfonamido-substituted aromatic ketones resulted in high (E)-stereoselectivity. In order to understand the origin of this high (E)-selectivity, a semiempirical conformational analysis of the four uncharged diastereomeric oxaphosphetane intermediates was performed with a cumulatively modified sampling procedure to generate initial conformations, followed by full energy optimization. Computational studies of the unsubstituted and 4-nitrophenyl-substituted oxaphosphetane intermediates were consistent with the low (Z)stereoselectivity observed. The results in the calculations of the aryl sulfonamido-substituted intermediate likewise were consistent with the high (E)-stereoselectivity observed. Calculations of the potassium-coordinated acid anion of the latter species were also performed. All calculations supported interaction of the sulfonamido and carboxylate groups by either hydrogen bonding or salt bridge formation which appears to effect the final stereochemical outcome. Furthermore, we investigated the stereoselectivity of Wittig reactions in which the sulfonamido NH or the carboxylate were removed. In both cases, the (Z)-olefin was formed preferentially, thereby supporting the existence of intramolecular hydrogen bonding or salt bridge formation.

  DOI：

  10.1021/jo00106a029
• 作为产物：
  描述：

  4-溴-N-甲基苯胺 在 苯磺酰氯 作用下， 以 吡啶 为溶剂， 生成 N-(4-bromophenyl)-N-methyl-benzenesulfonamide
  参考文献：
  名称：

  Heterocyclic arylsulfonamidobenzylic compounds

  摘要：

  提供了杂环芳基磺酰胺基苯基化合物，可用于治疗脂质紊乱、代谢紊乱和细胞增殖性疾病。

  公开号：

  US20030220339A1

文献信息

• Nanosized CdS as a Reusable Photocatalyst: The Study of Different Reaction Pathways between Tertiary Amines and Aryl Sulfonyl Chlorides through Visible-Light-Induced N-Dealkylation and C–H Activation Processes
  作者：Somayeh Firoozi、Mona Hosseini-Sarvari

  DOI：10.1021/acs.joc.0c02263

  日期：2021.2.5

  It has been found that the final products of the reaction of sulfonyl chlorides and tertiary amines in the presence of cadmium sulfide nanoparticles under visible light irradiation are highly dependent on the applied reaction conditions. Interestingly, with the change of a reaction condition, different pathways were conducted (visible-light-induced N-dealkylation or sp3 and sp2 C–H activation) that

  已经发现，在可见光辐射下，在硫化镉纳米颗粒存在下，磺酰氯和叔胺反应的最终产物高度依赖于所应用的反应条件。有趣的是，随着反应条件的改变，进行了不同的途径（可见光诱导的N-脱烷基或sp 3和sp 2C–H活化）导致产生不同的产物，例如仲胺和各种磺酰基化合物。值得注意的是，所有这些反应都是在可见光辐射下和在没有良性溶剂的情况下在无溶剂或无溶剂条件下的空气气氛下进行的。在这项研究过程中，CdS纳米颗粒作为可负担的，多相的和可回收的光催化剂被设计，成功合成并充分表征并应用于这些方案。在这些研究中，由叔胺氧化产生的中间体在光致电子转移（PET）过程中被捕获。使用可见光辐照作为可再生能源的同时，反应可在各种底物上有效地进行，从而在相对短的时间内以良好至极好的收率得到相应的产物。这些过程中的大多数都是新颖​​的，或者在成本效益，安全性和简化性方面优于已发布的报告。
• Arylsulfonamidobenzylic compounds
  申请人：Tularik Inc.

  公开号：US20030229093A1

  公开（公告）日：2003-12-11

  Arylsulfonamidobenzyl alcohols, amines and sulfonamides are provided which are useful in treating lipid disorders, metabolic diseases and cell-proliferative diseases.

  提供了对芳基磺胺基苄醇、胺和磺胺类化合物，这些化合物在治疗脂质紊乱、代谢性疾病和细胞增殖性疾病方面具有用处。
• Development of novel silanol-based human pregnane X receptor (PXR) agonists with improved receptor selectivity
  作者：Hirozumi Toyama、Hitoshi Shirakawa、Michio Komai、Yuichi Hashimoto、Shinya Fujii

  DOI：10.1016/j.bmc.2018.07.038

  日期：2018.8

  Pregnane X receptor (PXR) is a ligand-dependent transcription factor that is considered to be a potential therapeutic target for multiple diseases. Herein, we report the development and structure-activity relationship studies of a new series of hPXR agonists. Focusing on our recently developed silanol-sulfonamide scaffold, we developed the potent hPXR agonist 28, which shows good selectivity over hLXR alpha and beta, hFXR, and hROR alpha and gamma. Examination of the structure-activity relationship suggested a possible strategy to manipulate the selectivity. Docking simulation indicated the presence of an additional binding cavity and polar contacts in the ligand-binding pocket of hPXR. This information should be helpful for the future development of more potent and selective hPXR ligands.
• Discovery of a new binding mode for a series of liver X receptor agonists
  作者：David J. Kopecky、Xian Yun Jiao、Ben Fisher、Sharon McKendry、Marc Labelle、Derek E. Piper、Peter Coward、Andrew K. Shiau、Patrick Escaron、Jean Danao、Anne Chai、Juan Jaen、Frank Kayser

  DOI：10.1016/j.bmcl.2012.02.028

  日期：2012.4

  Structural modification of a series of dual LXR alpha/beta agonists led to the identification of a new class of LXR beta partial agonists. An X-ray co-crystal structure shows that a representative member of this series, pyrrole 5, binds to LXR beta with a reversed orientation compared to 1. (C) 2012 Elsevier Ltd. All rights reserved.
• HETEROCYCLIC ARYLSULFONAMIDOBENZYLIC COMPOUNDS
  申请人：Tularik Inc.

  公开号：EP1476425A2

  公开（公告）日：2004-11-17