N-(苯磺酰基)-4-甲氧基苯甲酰胺 | 22017-48-7

• 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-(苯磺酰基)-4-甲氧基苯甲酰胺
• 英文名称: 4-methoxy-N-(phenylsulfonyl)benzamide
• 英文别名: N-(4-methoxybenzoyl)benzenesulfonamide；N-(Benzenesulfonyl)-4-methoxybenzamide
• CAS: 22017-48-7
• 化学式: C₁₄H₁₃NO₄S
• 分子量: 291.328
• InChiKey: NKOOPWUVVICBSK-UHFFFAOYSA-N

物化性质

• 熔点：
  145 °C
• 密度：
  1.303±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：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-溴丙烯 、 N-(苯磺酰基)-4-甲氧基苯甲酰胺 生成 N-(benzenesulfonyl)-4-methoxy-N-prop-2-enylbenzamide
  参考文献：
  名称：

  DE2744137

  摘要：

  公开号：
• 作为产物：
  描述：

  4-甲氧基苯甲酸叔丁酯 在 三氯化磷 作用下， 以 乙腈 为溶剂， 反应 14.0h， 生成 N-(苯磺酰基)-4-甲氧基苯甲酰胺
  参考文献：
  名称：

  PCl 3介导的酰氯形成对叔丁基酯进行酯交换和氨解

  摘要：

  在空气中一锅中开发了PCl 3介导的叔丁基酯向酯和酰胺的转化。生物活性分子骨架的合成和克级反应突显了这种新颖的方案。机理研究表明，这种转化涉及原位形成酰氯，然后与醇或胺反应以提供所需的产物。

  DOI：

  10.1177/1747519820987530

文献信息

• Highly Efficient One-Pot Synthesis of N-Acylsulfonamides Using Cyanuric Chloride at Room Temperature
  作者：Mohammad Soltani Rad、Ali Khalafi-Nezhad、Zeinab Asrari、Somayeh Behrouz

  DOI：10.1055/s-0029-1218819

  日期：2010.8

  A highly efficient and very mild one-pot synthesis of N-acylsulfonamides is described using cyanuric chloride. In this synthesis, structurally diverse carboxylic acids and sulfonamides are reacted in the presence of cyanuric chloride, triethylamine, and alumina in anhydrous acetonitrile at room temperature to afford various N-acylsulfonamides in excellent yields.

  本文描述了一种使用氰尿酰氯的高效且温和的一锅法合成N-酰基磺酰胺的方法。在这种合成方法中，结构多样的羧酸和磺胺在氰尿酰氯、三乙胺和氧化铝的存在下，于室温下在无水乙腈中反应，得到了产率极高的各种N-酰基磺酰胺。
• A Study of Transmission Effects of Sulfonyl and Carbonyl Groups
  作者：Miroslav Ludwig、Patrik Pařík、Jiří Kulhánek

  DOI：10.1135/cccc19950841

  日期：——

  Seventeen p-substituted N-phenylsulfonylbenzamides of general formulas XC₆H₄SO₂NHCOC₆H₅ and C₆H₅SO₂NHCOC₆H₄X have been synthesized and their structure has been confirmed by elemental analysis and ¹H NMR spectra. The dissociation constants of all the compounds have been measured by potentiometric titration in methanol, acetonitrile, dimethylformamide, dimethyl sulfoxide, and pyridine. The obtained pK_HA values have been correlated with three sets of Hammett substituent constants using simple or double linear regression. The solvent and substituent effects are discussed on the basis of experimental results, and the difference between the substituent effects from sulfonamide and benzamide sections is evaluated. It has been found that due to the extensive delocalization of negative charge in the conjugated base the transmission effects of carbonyl and sulfonyl groups on the transmission of substituent effect are roughly the same. The experimental data have been interpreted by the methods with latent variables: the principal component analysis (PCA), the conjugated deviation analysis (CDA), and the method of projection to latent structures (PLS). The results obtained by these procedures were similar.

  通用公式为XC6H4SO2NHCOC6H5和C6H5SO2NHCOC6H4X的十七个p-取代N-苯磺酰基苯甲酰胺已经合成，并通过元素分析和1H NMR光谱确认了它们的结构。所有化合物的解离常数已通过在甲醇、乙腈、二甲基甲酰胺、二甲基亚砜和吡啶中的电位滴定测定。通过简单或双线性回归，已将获得的pKHA值与三组Hammett取代基常数相关联。根据实验结果讨论了溶剂和取代基效应，并评估了磺酰胺和苯甲酰胺部分的取代基效应之间的差异。发现由于在共轭碱中负电荷的广泛共轭作用，羰基和磺酰基对取代基效应传递的传输效应大致相同。实验数据已通过具有潜在变量的方法进行解释：主成分分析（PCA）、共轭偏差分析（CDA）和潜在结构投影方法（PLS）。这些程序得到的结果是相似的。
• Development of an Acyl Sulfonamide Anti-Proliferative Agent, LY573636·Na
  作者：Matthew H. Yates、Neil J. Kallman、Christopher P. Ley、Jeffrey N. Wei

  DOI：10.1021/op800210x

  日期：2009.3.20

  The synthesis of 5-bromo-thiophene-2-sulfonic acid 2,4-dichlorobenzoylamide sodium salt on multikilogram scale is described. The initial clinical supplies were made using carbonyl diimidazole to converge the two fragments. A more efficient acid chloride process has been developed, which also provides better control of impurities and color throughout the synthesis.
• DOLYUK V. G.; KREMLEV M. M.; ROVINSKIJ M. S., VOPR. XIMII I XIM. TEXNOL., RESP. MEZHVED. TEMAT. NAUCH.-TEXN. SB., 1975,+
  作者：DOLYUK V. G.、 KREMLEV M. M.、 ROVINSKIJ M. S.

  DOI：——

  日期：——
• PCl₃-mediated transesterification and aminolysis of <i>tert</i>-butyl esters via acid chloride formation
  作者：Xiaofang Wu、Lei Zhou、Fangshao Li、Jing Xiao

  DOI：10.1177/1747519820987530

  日期：2021.5

  A PCl3-mediated conversion of tert-butyl esters into esters and amides in one-pot under air is developed. This novel protocol is highlighted by the synthesis of skeletons of bioactive molecules and gram-scale reactions. Mechanistic studies revealed that this transformation involves the formation of an acid chloride in situ, which is followed by reactions with alcohols or amines to afford the desired

  在空气中一锅中开发了PCl 3介导的叔丁基酯向酯和酰胺的转化。生物活性分子骨架的合成和克级反应突显了这种新颖的方案。机理研究表明，这种转化涉及原位形成酰氯，然后与醇或胺反应以提供所需的产物。