N-(2-chlorophenethyl)-4-methylbenzenesulfonamide | 430432-26-1

• 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-(2-chlorophenethyl)-4-methylbenzenesulfonamide
• 英文别名: N-[2-(2-chlorophenyl)ethyl]-4-methylbenzenesulfonamide
• CAS: 430432-26-1
• 化学式: C₁₅H₁₆ClNO₂S
• 分子量: 309.817
• InChiKey: YLPGHYKMGMZGGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 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：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (甲硫基)乙酸乙酯 、 N-(2-chlorophenethyl)-4-methylbenzenesulfonamide 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 1,2-二氯乙烷 为溶剂， 以61%的产率得到1-carbethoxy-5-chloro-2-p-tosyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Kang, Iou-Jiun; Wang, Huey-Min; Su, Chien-Hsing, Heterocycles, 2002, vol. 57, # 1, p. 1 - 4

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(2-氯苯基)丙酰氯 在 sodium azide 、 丙酮 作用下， 生成 N-(2-chlorophenethyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  148.对异喹啉化学的贡献。第一部分。二氨基-1-苯基异喹啉甲硫醇的合成，以寻找新的锥虫病，以及关于1-苯基异喹啉硝化的一些观察结果

  摘要：

  DOI：

  10.1039/jr9490000696

文献信息

• Electrochemical C−H Amidation of Heteroarenes with<i>N</i>‐Alkyl Sulfonamides in Aqueous Medium
  作者：Yan Zhang、Zhipeng Lin、Lutz Ackermann

  DOI：10.1002/chem.202004229

  日期：2021.1.4

  The construction of C−N bonds by free radical reactions represents a powerful synthetic approach for direct C−H amidations of arenes or heteroarenes. Developing efficient and more environmentally friendly synthetic methods for C−H amidation reactions remains highly desirable. Herein, metal‐free electrochemical oxidative dehydrogenative C−H amidations of heteroarenes with N‐alkylsulfonamides have been

  通过自由基反应构建C-N键代表了对芳烃或杂芳烃直接C-H酰胺化的强大合成方法。为CH酰胺化反应开发高效且对环境友好的合成方法仍然是非常可取的。在此，杂芳烃与N-烷基磺酰胺的无金属电化学氧化脱氢CHH酰胺化反应已经完成。不含催化剂和化学氧化剂的CHH酰胺化反应范围广，并使用电作为绿色和唯一的氧化剂。各种杂芳烃，包括吲哚，吡咯，苯并呋喃和苯并噻吩，都经过了这种C（sp 2）-H氮化。循环伏安法研究和控制实验为无金属电催化直接生成以氮为中心的自由基提供了证据。
• New Syntheses of 1-Benzoyltetrahydroisoquinoline Derivatives Using Polymer-supported Bis(trifluoroacetoxyiodo)benzene
  作者：Ling-Ching Chen、Hsin-Yu Huang、Rei-Sheu Hou、Huey-Min Wang

  DOI：10.3987/com-05-10433

  日期：——

  The reaction of N-benzenesulfonyl-β-phenethylamines with α-benzoyl sulfides using polymer-supported bis(trifluoroacetoxyiodo)benzene (PSBTI) gives moderate to good yields of the corresponding 1-benzoyltetrahydroisoquinoline derivatives.

  使用聚合物负载的双（三氟乙酰氧基碘）苯 (PSBTI) 使 N-苯磺酰基-β-苯乙胺与 α-苯甲酰硫化物反应，得到相应的 1-苯甲酰基四氢异喹啉衍生物的产率适中至良好。
• Development of Photoredox Cross-Electrophile Coupling of Strained Heterocycles with Aryl Bromides Using High-Throughput Experimentation for Library Construction
  作者：Yukiko Mori、Mutsuyo Hayashi、Ryuma Sato、Kuninori Tai、Tsuyoshi Nagase

  DOI：10.1021/acs.orglett.3c01821

  日期：2023.8.4

  cross-coupling reaction of aryl halides with strained aliphatic heterocycles facilitated via a ring-opening reaction. This methodology was found to be applicable to medicinally relevant substrates including Boc-protected strained aliphatic heterocycles and (hetero)aryl bromides and was used for compound library construction via parallel medicinal chemistry. Furthermore, the coupling reactions were shown

  采用微型高通量实验开发了芳基卤化物与张力脂肪族杂环通过开环反应促进的光氧化还原辅助还原交叉偶联反应。该方法被发现适用于医学相关底物，包括 Boc 保护的应变脂肪族杂环和（杂）芳基溴，并用于通过平行药物化学构建化合物库。此外，通过连续流动反应，偶联反应可扩展到克级。还讨论了可能的反应机理。
• Ytterbium Triflate-catalysed Synthesis of Ethyl 1,2,3,4-Tetrahydroisoquinoline-1-carboxylates Using Ethyl Chloro(phenylselanyl)acetate
  作者：Ling-Ching Chen、Huey-Min Wang、Iou-Jiun Kang

  DOI：10.3987/com-03-9799

  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.