4-bromo-N-methyl-N-phenylbenzenesulfonamide | 64999-91-3

• 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-bromo-N-methyl-N-phenylbenzenesulfonamide
• CAS: 64999-91-3
• 化学式: C₁₃H₁₂BrNO₂S
• 分子量: 326.214
• InChiKey: VAKOAGKCNQSYBA-UHFFFAOYSA-N

物化性质

• 沸点：
  419.1±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

• 储存条件：
  2-8℃

反应信息

• 作为反应物：
  描述：

  4-bromo-N-methyl-N-phenylbenzenesulfonamide 在 palladium diacetate 、 sodium hydride 、 sodium carbonate 、 三苯基膦 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 生成 methyl 3-(4'-(N-methyl-N-phenylsulfamoyl)-3-nitro-[1,1'-biphenyl]-4-yl)-2-oxopropanoate
  参考文献：
  名称：

  Synthesis of sulfonamide-containing N-hydroxyindole-2-carboxylates as inhibitors of human lactate dehydrogenase-isoform 5

  摘要：

  N-Hydroxyindole-2-carboxylates possessing sulfonamide-substituents at either position 5 or 6 were designed and synthesized. The inhibitory activities of these compounds against isoforms 1 and 5 of human lactate dehydrogenase were analysed, and K-i values of the most efficient inhibitors were determined by standard enzyme kinetic studies. Some of these compounds displayed state-of-the-art inhibitory potencies against isoform 5 (K-i values as low as 5.6 mu M) and behaved as competitive inhibitors versus both the substrate and the cofactor. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.031
• 作为产物：
  描述：

  N-甲基苯胺 、 4-溴苯磺酰氯 在 四丁基硫酸氢铵 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.0h， 以98%的产率得到4-bromo-N-methyl-N-phenylbenzenesulfonamide
  参考文献：
  名称：

  Novel N-methylsulfonamide and retro-N-methylsulfonamide derivatives as 17β-hydroxysteroid dehydrogenase type 2 (17β-HSD2) inhibitors with good ADME-related physicochemical parameters

  摘要：

  Under physiological conditions healthy bones are maintained by a well tightened balance between osteoclast (OCs) and osteoblast (OBs) activity. Disruption of this balance leads to osteoporosis characterized by decline in bone function and skeletal rigidity. Inhibition of 17 beta-hydroxysteroid dehydrogenase type 2 (17 beta-HSD2) could help maintaining the appropriate bone mass density by increasing the level of estradiol and testosterone in bone. Herein, we described the synthesis, the physicochemical properties and the biological evaluation of novel N-methylsulfonamide and retro-N-methylsulfonamide derivatives as 17 beta-HSD2 inhibitors showing high potency (compound 10f, IC50 = 23 n M), with a good selectivity toward 17 beta-HSD1 (the isoenzyme responsible of the reverse reaction), and a likely good in vitro ADME profile. It was also shown that the acidity of the phenolic hydroxy correlates with the inhibitory potency, suggesting pKa as a predictive parameter for the activity of this class of inhibitors. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.026

文献信息

• Aromatization as an Impetus to Harness Ketones for Metallaphotoredox-Catalyzed Benzoylation/Benzylation of (Hetero)arenes
  作者：Shao-Chi Lee、Li-Yun Li、Zong-Nan Tsai、Yi-Hsin Lee、Yong-Ting Tsao、Pin-Gong Huang、Cheng-Ku Cheng、Heng-Bo Lin、Ting-Wei Chen、Chung-Hsin Yang、Cheng-Chau Chiu、Hsuan-Hung Liao

  DOI：10.1021/acs.orglett.1c03672

  日期：2022.1.14

  simple condensation first converts ketones into prearomatic intermediates that then act as activated radical sources for cross-coupling with aryl halides. Our strategy enables the direct benzylation/benzoylation of (hetero)arenes under mild reaction conditions with high functional group tolerance.

  在此，我们报道了在 Ni/光氧化还原双重催化下，酮作为自由基交叉偶联反应的原料。在这种方法中，简单的缩合首先将酮转化为前芳香族中间体，然后作为活化自由基源与芳基卤化物进行交叉偶联。我们的策略能够在具有高官能团耐受性的温和反应条件下实现（杂）芳烃的直接苄基化/苯甲酰化。
• NaI-Catalyzed Oxidative Amination of Aromatic Sodium Sulfinates: Synergetic Effect of Ethylene Dibromide and Air as Oxidants
  作者：Ying Fu、Quan-Zhou Li、Qin-Shan Xu、Helmut Hügel、Ming-Peng Li、Zhengyin Du

  DOI：10.1002/ejoc.201801386

  日期：2018.12.31

  A novel NaI-catalyzed oxidative amination of sodium sulfinates, employing both ethylene dibromide (EDB) and air as the oxidants, is described. EDB was first demonstrated to be a promising mild organic oxidant that in air, converted NaI into molecular iodine to promote the cross-coupling reactions of aromatic sodium sulfinates with amines to produce arylsulfonamides. Mechanistic studies indicated that

  描述了一种使用二溴化乙烯 (EDB) 和空气作为氧化剂的新型 NaI 催化亚磺酸钠氧化胺化。EDB 首次被证明是一种有前途的温和有机氧化剂，它在空气中将 NaI 转化为分子碘，以促进芳族亚磺酸钠与胺的交叉偶联反应，生成芳基磺酰胺。机理研究表明，反应过程中可能涉及自由基途径。
• Desulfurative Ni-Catalyzed Reductive Cross-Coupling of Benzyl Mercaptans/Mercaptoacetates with Aryl Halides
  作者：Che-Ming Hsu、Shao-Chi Lee、Hao-En Tsai、Yong-Ting Tsao、Cheng-Lin Chan、Shinje Miñoza、Zong-Nan Tsai、Li-Yun Li、Hsuan-Hung Liao

  DOI：10.1021/acs.joc.1c02897

  日期：2022.3.4

  scaffold, into sp3-hybridized thiols to activate the C–S bond. Using a Ni catalyst with MgBr2 as an additive, the S group can be removed to yield an aliphatic radical that can react with an aryl halide in a reductive cross-coupling.

  从天然硫醇中进行 C-S 活化和脱硫具有挑战性，这限制了它们在有机合成中作为原料的应用，尽管它们天然丰富。在此，我们将用作氧化还原活性支架的全氟/多氟芳基部分引入 sp 3杂化硫醇中以激活 C-S 键。使用具有 MgBr 2作为添加剂的 Ni 催化剂，可以去除 S 基团以产生可以与芳基卤化物在还原交叉偶联中反应的脂肪族自由基。
• US4111834A
  申请人：——

  公开号：US4111834A

  公开（公告）日：1978-09-05
• US4161461A
  申请人：——

  公开号：US4161461A

  公开（公告）日：1979-07-17

表征谱图