N-(4-methoxy-phenethyl)-benzenesulfonamide | 175287-92-0

• 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-methoxy-phenethyl)-benzenesulfonamide
• 英文别名: N-Benzolsulfonyl-4-methoxy-β-phenaethylamin；N-(4-Methoxy-phenaethyl)-benzolsulfonamid；Cambridge id 6121447；N-[2-(4-methoxyphenyl)ethyl]benzenesulfonamide
• CAS: 175287-92-0
• 化学式: C₁₅H₁₇NO₃S
• 分子量: 291.371
• InChiKey: UAFNTUPLYICDLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-methoxy-phenethyl)-benzenesulfonamide 在 氢化钾 、 xylene 作用下， 生成 4,4'-(3,7-diaza-nonanediyl)-di-phenol
  参考文献：
  名称：

  Synthetical experiments in the group of sympathomimetics, part IV

  摘要：

  DOI：

  10.1007/bf03048965
• 作为产物：
  描述：

  3-(4-甲氧基苯基)-丙酰胺 在 氢氧化钾 、 次溴酸钾 、 苯 作用下， 生成 N-(4-methoxy-phenethyl)-benzenesulfonamide
  参考文献：
  名称：

  Interactive Effect of Support From Family and Friends in Visually Impaired Elders

  摘要：

  The interactive relationship of high and low friend and family support for adaptation to chronic vision impairment was examined in 241 men and women. Two 2 (High/Low Family Support) X 2 (High/Low Friend Support) X 2 (Gender) multivariate analyses of covariance tested for psychological well-being, one with qualitative support measures, the other with quantitative support measures. Two analyses of covariance models tested for adaptation to vision loss. A significant multivariate 3-way interaction effect for qualitative support was found. Women with high support from both friends and family had better psychological well-being, whereas men with high support from both friends and family or just from family had better psychological well-being. Two univariate main effects showed that participants with high qualitative friend support and high quantitative family support had better adaptation to vision loss. Findings demonstrate the complexity of measuring and understanding relationships among social support, well-being, and domain-specific adaptation to chronic impairment.

  DOI：

  10.1093/geronb/56.6.p374

文献信息

• Ionic Liquid in Organic Synthesis: The Pictet-Spengler Reaction
  作者：Ling-Ching Chen、Huey-Min Wang、Rei-Sheu Hou、Hsin-Yu Huang

  DOI：10.3987/com-06-10778

  日期：——

  have demonstrated the use of the room temperature ionic liquid, 1-butyl-3-methylimidazoliumhexafluorophosphate ([bmim]PF 6 ), as an environmentally benign solvent for the preparation of 2-benzenesulfonyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid ethyl ester derivatives through Pictet-Spengler reaction using phenyliodine(III) bis(trifluoroacetate) (PIFA) under mild conditions.

  我们已经证明了使用室温离子液体 1-丁基-3-甲基咪唑鎓六氟磷酸盐 ([bmim]PF 6 ) 作为制备 2-苯磺酰基-1,2,3,4-四氢异喹啉的环境友好溶剂- 1-羧酸乙酯衍生物通过 PIctet-Spengler 反应，在温和条件下使用苯碘 (III) 双（三氟乙酸） (PIFA)。
• A Novel Synthesis of Isoquinolines Containing an Electron Withdrawing Substituent
  作者：Koichiro Yamada、Harumichi Kohno

  DOI：10.3987/com-98-8362

  日期：——
• A Novel Cyclization of Electron Deficient N-Benzenesulfonyl-b-phenethylamines Using Ethyl Chloro(methylthio)acetate. Synthesis of Ethyl 1,2,3,4-Tetrahydroisoquinoline-1-carboxylates
  作者：Yasuo Sekine、Harumichi Kohno

  DOI：10.3987/com-95-s47

  日期：——
• Organo‐Photocatalytic Anti‐Markovnikov Hydroamidation of Alkenes with Sulfonyl Azides: A Combined Experimental and Computational Study
  作者：Rui Fu、Mengyu Xu、Yujing Wang、Xinxin Wu、Xiaoguang Bao

  DOI：10.1002/anie.202406069

  日期：2024.6.21

  The construction of C(sp3)−N bonds via direct N‐centered radical addition with olefins under benign conditions is a desirable but challenging strategy. Herein, we describe an organo‐photocatalytic approach to achieve anti‐Markovnikov alkene hydroamidation with sulfonyl azides in a highly efficient manner under transition‐metal‐free and mild conditions. A broad range of substrates, including both activated and unactivated alkenes, are suitable for this protocol, providing a convenient and practical method to construct sulfonylamide derivatives. A synergistic experimental and computational mechanistic study suggests that the additive, Hantzsch ester (HE), might undergo a triplet‐triplet energy transfer manner to achieve photosensitization by the organo‐photocatalyst under visible light irradiation. Next, the resulted triplet excited state 3HE* could lead to a homolytic cleavage of C4−H bond, which triggers a straightforward H‐atom transfer (HAT) style in converting sulfonyl azide to the corresponding key amidyl radical. Subsequently, radical addition of the amidyl radical to alkenes followed by HAT from p‐toluenethiol could proceed to afford the desired anti‐Markovnikov hydroamidation product. It is worth noting that mechanistic pathway bifurcation could be possible for this reaction. A feasible radical chain propagation mechanistic pathway is also proposed to rationalize the high efficiency of this reaction.