N-(4-aminophenethyl)-4-methylbenzenesulfonamide | 111437-08-2

• 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-aminophenethyl)-4-methylbenzenesulfonamide
• 英文别名: N-[2-(4-Amino-phenyl)-ethyl]-4-methyl-benzenesulfonamide；N-[2-(4-aminophenyl)ethyl]-4-methylbenzenesulfonamide
• CAS: 111437-08-2
• 化学式: C₁₅H₁₈N₂O₂S
• 分子量: 290.386
• InChiKey: DURXTCJGPQFVPS-UHFFFAOYSA-N

物化性质

• 沸点：
  489.6±55.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-aminophenethyl)-4-methylbenzenesulfonamide 在 盐酸 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 N-[2-[4-[[(2R)-2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]amino]phenyl]ethyl]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Synthesis and Evaluation of Potent and Selective β₃ Adrenergic Receptor Agonists Containing Acylsulfonamide, Sulfonylsulfonamide, and Sulfonylurea Carboxylic Acid Isosteres

  摘要：

  Starting from phenethanolamine aniline leads 3a and 3b, we have identified a series of functionally potent and selective beta(3) adrenergic receptor (AR) agonists containing acylsulfonamide, sulfonylsulfonamide, or sulfonylurea groups within the aniline phenethanolamine series. In beta(3) beta(2), and beta(1) AR cAMP functional assays, 3a and other right-hand side (RHS) carboxylate analogues were found to be full agonists that were modestly selective against beta(1) or beta(2) ARs, while analogues lacking RHS acid functionality were active at beta(3) AR but not selective. Replacement of the carboxylate with acylthiazole and acylmethylsulfone gave potent, but only modestly selective, compounds. Increasing the size of the RHS sulfonamide substituent with phenyl or p-toluene afforded compounds with good potency and functional selectivity (beta(3) AR pEC(50) greater than 8; beta(1) and beta(2) AR selectivity greater than 40- and 500-fold, respectively). Our SAR studies suggest that the potency and selectivity profile of the best analogues reported here is a result of both the steric bulk and acidity of the RHS sulfonamide NH group. Although all of the analogues had a pharmacokinetic half-life of less than 2 h, acylsulfonamides 43 and 44 did show moderately low clearance in dogs. These two compounds were further evaluated by thermographic imaging in mice and were found to produce a robust thermogenic response via oral administration.

  DOI：

  10.1021/jm0101500
• 作为产物：
  描述：

  对硝基苯乙腈 在 platinum(IV) oxide sodium tetrahydroborate 、 三氟化硼 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 N-(4-aminophenethyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Chemistry of synthetic receptors and functional group arrays. 7. Molecular armatures. Synthesis and structure of Troeger's base analogs derived from 4-, 2,4-, 3,4-, and 2,4,5-substituted aniline derivatives

  摘要：

  DOI：

  10.1021/jo00236a020

文献信息

• Phenethylamino sulfamic acids
  申请人：The Procter & Gamble Company

  公开号：US20040167183A1

  公开（公告）日：2004-08-26

  Compounds of formula (I): 1 are effective in the treatment of protein tyrosine phosphatase (PTPase) mediated disorders such as diabetes.

  公式（I）的化合物在治疗蛋白酪氨酸磷酸酶（PTPase）介导的疾病，如糖尿病方面具有有效性。
• Aggregates of the pentacenequinone derivative as reactors for the preparation of Ag@Cu₂O core–shell NPs: an active photocatalyst for Suzuki and Suzuki type coupling reactions
  作者：Kamaldeep Sharma、Manoj Kumar、Vandana Bhalla

  DOI：10.1039/c5cc03907j

  日期：——

  Aggregates of the pentacenequinone derivative stabilized Ag@Cu₂O core–shell nanoparticles (NPs) enabled efficient visible light harvesting to catalyse the palladium free Suzuki–Miyaura and Suzuki type cross coupling reactions at room temperature.

  五氯酮衍生物稳定的Ag@Cu₂O核壳纳米颗粒的聚集体，能够有效地利用可见光来催化室温下无钯的Suzuki–Miyaura和Suzuki型交叉偶联反应。
• A supramolecular ensemble of a PBI derivative and Cu₂O NPs: potential photocatalysts for the Suzuki and Suzuki type coupling reactions
  作者：Gurpreet Singh、Manoj Kumar、Kamaldeep Sharma、Vandana Bhalla

  DOI：10.1039/c5gc03012a

  日期：——

  The in situ generated supramolecular ensemble (2:Cu₂O) of Cu₂O NPs and aggregates of PBI derivative 2 exhibited excellent photocatalytic efficiency in the Suzuki–Miyaura and Suzuki type cross-coupling reactions under mild and eco-friendly conditions.

  在温和且环保的条件下，由Cu₂O NPs和PBI衍生物2的聚集体（2：Cu₂O）所生成的原位超分子集合体，在Suzuki-Miyaura和Suzuki类型的交叉偶联反应中表现出优秀的光催化效率。
• An Acid‐Controlled Method for the Regioselective Functionalization of Anilines over Aliphatic Amines
  作者：Bowen Li、Yulun Hu、Gregory P. Tochtrop

  DOI：10.1002/chem.202301336

  日期：2023.10.23

  Regioselective functionalization of anilines in the presence of aliphatic amines is illustrated utilizing classic conditions for the Baeyer-Mills reaction. Further, the defined principles of reactivity are shown to be broadly extended to other electrophiles.

  利用 Baeyer-Mills 反应的经典条件说明了在脂肪胺存在下苯胺的区域选择性官能化。此外，所定义的反应性原理被证明可以广泛扩展到其他亲电子试剂。
• [EN] PHENETHYLAMINO SULFAMIC ACIDS<br/>[FR] ACIDES SULFAMIQUES DE PHENETHYLAMINO
  申请人：PROCTER & GAMBLE

  公开号：WO2004074238A1

  公开（公告）日：2004-09-02

  Compounds of formula (I): (I)are effective in the treatment of protein tyrosine phosphatase (PTPase) mediated disorders such as diabetes.