N-(4-羟基-苯基)-4,n-二甲基苯磺酰胺 | 124772-05-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(4-羟基-苯基)-4,n-二甲基苯磺酰胺
• 英文名称: N-(4-hydroxyphenyl)-N,4-dimethylbenzenesulfonamide
• CAS: 124772-05-0
• 化学式: C₁₄H₁₅NO₃S
• mdl: MFCD00593667
• 分子量: 277.344
• InChiKey: PWCDUUXCNJSZRC-UHFFFAOYSA-N

物化性质

• 熔点：
  138 °C
• 沸点：
  462.2±55.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  N-(4-羟基-苯基)-4,n-二甲基苯磺酰胺 在 盐酸 、 sodium ethanolate 作用下， 生成 N,N'-dimethyl-4,4'-pentanediyldioxy-di-aniline
  参考文献：
  名称：

  Yang et al., Huaxue Xuebao/Acta Chimica Sinica, 1956, vol. 22, p. 472,474

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(4-羟基苯基)-4-甲基苯磺酰胺 在 sodium hydroxide 、 sodium methylate 作用下， 生成 N-(4-羟基-苯基)-4,n-二甲基苯磺酰胺
  参考文献：
  名称：

  THE S_N MECHANISM IN AROMATIC COMPOUNDS, PART XI. SOME REACTIONS OF AMINODINITRODIARYL ETHERS

  摘要：

  DOI：

  10.1021/jo01375a023

文献信息

• Brønsted Acid-Catalyzed Intramolecular α-Arylation of Ketones with Phenolic Nucleophiles via Oxy-Allyl Cation Intermediates
  作者：Yusuke Aota、Yuki Doko、Taichi Kano、Keiji Maruoka

  DOI：10.1002/ejoc.202000169

  日期：2020.3.31

  Catalytic α‐arylation of ketones in an umpolung fashion was demonstrated through nucleophilic addition of phenol derivatives to the electrophilic oxy‐allyl cation intermediates, allowing the formation of ketones bearing an all carbon quaternary center at the α‐position.

  通过将苯酚衍生物亲核加成到亲电子性氧基烯丙基阳离子中间体上，证明了酮的催化α-芳基化反应成为可能，从而形成了在α-位带有全碳四元中心的酮。
• O- and N-Substituted Derivatives of Planetol as Valuable Bioactive Compounds
  作者：Misbah Irshad、Muhammad Athar Abbasi、Aziz-Ur-Rehman、Shahid Rasool、Sabahat Zahra Siddiqui、Irshad Ahmad、Muhammad Ashraf、Muhammad Arif Lodhi、Syed Babar Jamal

  DOI：10.14233/ajchem.2014.16109

  日期：——

  The compounds bearing sulfamoyl and acetamoyl groups have been found to show various biological activities. In the present research work, a series of O- and N-substituted derivatives were synthesized, starting with planetol (1). First N-methyl-4-hydroxyanilinium sulfate (1; planetol or metol) was treated with different aryl sulfonyl chlorides (2a-i) using aq. sodium carbonate solution as reaction medium to yield N-substituted derivatives 3a-i. The electrophile, N-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-bromoacetamide (5) was prepared by the reaction of 2,3-dihydro-1,4-benzodioxin-6-amine (4) and 2-bromoacetylbromide in a weak basic aqueous medium. The target O-substituted molecules 6a-i, were synthesized by gearing up the electrophile 5, with the molecules 3a-i, in a polar aprotic solvent using LiH as an activator. The proposed structures of all the synthesized molecules were corroborated by IR, 1H NMR and EIMS spectral data. The in vitro enzyme inhibition and antibacterial studies rendered the synthesized molecules as better cholinesterase inhibitors and moderately better antibacterial agents. To explore the binding modes of the synthesized compounds, all of them were computationally docked against the active sites of acetyl cholinesterase (AChE), butyryl cholinesterase (BChE) and lipoxygenase (LOX). The compounds showed significant interactions and good correlation with the experimental data.

  具有磺酰胺基和乙酰胺基的化合物已被发现具有多种生物活性。在本研究工作中，以普兰诺尔（1）为起始物，合成了一系列O-和N-取代衍生物。首先，N-甲基-4-羟基苯胺硫酸盐（1；普兰诺尔或甲硫醇）在碳酸钠水溶液中与不同的芳基磺酰氯（2a-i）反应，生成N-取代衍生物3a-i。通过2,3-二氢-1,4-苯并二噁英-6-胺（4）与2-溴乙酰溴在弱碱性水溶液中的反应，合成了亲电试剂N-(2,3-二氢-1,4-苯并二噁英-6-基)-2-溴乙酰胺（5）。通过亲电试剂5与分子3a-i在极性非质子溶剂中以LiH为活化剂反应合成了目标O-取代分子6a-i。所有合成化合物的结构均通过IR、1H NMR和EIMS光谱数据得到验证。体外酶抑制和抗菌研究表明，合成化合物具有较好的胆碱酯酶抑制作用和中等抗菌活性。为了探索合成化合物的结合模式，所有化合物均在计算上与乙酰胆碱酯酶（AChE）、丁酰胆碱酯酶（BChE）和脂氧合酶（LOX）的活性位点对接。化合物显示出显著的相互作用，并与实验数据呈现良好相关性。
• Transition-Metal-Free and Visible-Light-Mediated Desulfonylation and Dehalogenation Reactions: Hantzsch Ester Anion as Electron and Hydrogen Atom Donor
  作者：Micaela D. Heredia、Walter D. Guerra、Silvia M. Barolo、Santiago J. Fornasier、Roberto A. Rossi、María E. Budén

  DOI：10.1021/acs.joc.0c01523

  日期：2020.11.6

  at rt. Alternately, a visible light method has been used for deprotection of N-methyl-N-arylsulfonamides with Hantzsch ester (HE) anion serving as the visible-light-absorbing reagent and electron and hydrogen atom donor to promote the desulfonylation reaction. The HE anion can be easily prepared in situ by reaction of the corresponding HE with KOtBu in DMSO at rt. Both protocols were further explored

  已开发出在室温（rt）和无过渡金属条件下进行N-和O-磺酰化的新方法。第一种方法涉及在室温下仅使用二甲基亚砜（DMSO）中的KO t Bu将各种N-磺酰基杂环和苯基苯磺酸盐以良好或优异的收率转化为相应的脱磺酰化产物。或者，已经使用可见光方法用作为可见光吸收剂的Hantzsch酯（HE）阴离子和电子和氢原子供体来促进N-甲基-N-芳基磺酰胺的脱保护，以促进脱磺酰化反应。HE阴离子可轻松就地制备通过在室温下将相应的HE与DMSO中的KO t Bu反应。进一步研究了两种方案的合成范围和机制方面，以合理化脱磺酰化工艺的关键特征。此外，HE阴离子在可见光照射下诱导芳基卤化物的还原脱卤反应。
• A Mild Heteroatom (O-, N-, and S-) Methylation Protocol Using Trimethyl Phosphate (TMP)–Ca(OH)2Combination
  作者：Yu Tang、Biao Yu

  DOI：10.1055/a-1731-3852

  日期：2022.5

  A mild heteroatom methylation protocol using trimethyl phosphate (TMP)–Ca(OH)2 combination has been developed, which proceeds in DMF, or water, or under neat conditions, at 80 °C or at room temperature. A series of O-, N-, and S-nucleophiles, including phenols, sulfonamides, N-heterocycles, such as 9H-carbazole, indole derivatives, and 1,8-naphthalimide, and aryl/alkyl thiols, are suitable substrates

  已开发出使用磷酸三甲酯 (TMP)-Ca(OH) 2组合的温和杂原子甲基化方案，该方案在 DMF 或水中，或在纯净条件下，在 80 °C 或室温下进行。一系列O-、N-和S-亲核试剂，包括苯酚、磺酰胺、N-杂环，例如 9 H-咔唑、吲哚衍生物和 1,8-萘酰亚胺，以及芳基/烷基硫醇，是这个协议。该协议的高效、操作简单、可扩展性、成本效益和环保性质使其成为传统碱基促进杂原子甲基化程序的有吸引力的替代方案。
• Catalytic hydroxylation of arylthianthrenium salts with nitrous oxide
  作者：Shengyang Ni、Josep Cornella

  DOI：10.1016/j.tet.2023.133602

  日期：2023.9

  protocol for the conversion of aryl thianthrenium salts to the corresponding phenols, by means of a nickel catalyst and N2O. The method tolerates various functional groups and permits the hydroxylaiton of functionalized molecules. Capitalizing on the high selectivity in the introduction of the thianthrene unit in aryl groups, the method represents a formal hydroxylation of aromatic C–H bonds.

  我们提出了一种催化方案，通过镍催化剂和 N 2 O 将芳基噻烯鎓盐转化为相应的酚类。该方法可耐受各种官能团并允许官能化分子的羟基化。利用在芳基中引入噻蒽单元的高选择性，该方法代表了芳香族 C-H 键的正式羟基化。