4-chloro-N-[2-(4-methoxyphenyl)ethyl]benzenesulfonamide

• 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: 4-chloro-N-[2-(4-methoxyphenyl)ethyl]benzenesulfonamide
• 化学式: C₁₅H₁₆ClNO₃S
• mdl: MFCD01185522
• 分子量: 325.8
• InChiKey: UYTAJIZGUZFXNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 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

• 作为产物：
  描述：

  4-氯苯磺酰氯 在 sodium azide 、 二氢吡啶 、 1,3-dicyano-5-fluoro-2,4,6-tris(diphenylamino)benzene 、 4-甲苯硫酚 作用下， 以 水 、 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 10.0h， 生成 4-chloro-N-[2-(4-methoxyphenyl)ethyl]benzenesulfonamide
  参考文献：
  名称：

  Organo‐Photocatalytic Anti‐Markovnikov Hydroamidation of Alkenes with Sulfonyl Azides: A Combined Experimental and Computational Study

  摘要：

  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.

  DOI：

  10.1002/anie.202406069

文献信息

• Phenoxyacetic acid derivatives, preparation thereof, pharmaceutical compositions comprising them and use
  申请人：TANABE SEIYAKU CO., LTD.

  公开号：EP0325245A1

  公开（公告）日：1989-07-26

  Novel phenoxyacetic acid derivative of the formula: wherein R is a substituted or unsubstituted phenyl group, naphthyl group or a sulfur-containing 5-membered hetero-monocyclic group, R¹, R², R³ and R⁴ are hydrogen atom, a lower alkyl group, a phenyl-­lower alkyl group or phenyl group, R⁵ is hydrogen atom or a lower alkyl group, R⁶ is carboxyl group, a protected carboxyl group, hydroxy group or a di(lower alkyl)-amino group, Ring A is a substituted or unsubstituted phenylene group, m is 0 or 1 and n is an integer of 0 to 5, provided that, when m is 0, (1) at least either one of R¹ to R⁴ is or/are a phenyl-lower alkyl group or phenyl group, (2) at least either one of R¹to R⁴ is or/are a lower alkyl group, and R⁶ is hydroxy group, or (3) all of R¹ to R⁴ are hydrogen atom, and Ring A is a substituted phenylene group, or a pharmaceutically acceptable salt thereof are disclosed. Said derivative (I) and a pharmaceutically aceptable salt thereof have a potent platelet aggregation-inhibiting activity. The derivative (I) is used for the prophylaxis or treatment of thrombotic diseases in warm-blooded animals. The invention includes a variety of prepara­tion methods for the above derivative (I) and pharma­ceutical compositions comprising said derivative (I) in therapeutically effective amounts.

  式中的新型苯氧乙酸衍生物： 其中 R 是取代或未取代的苯基、萘基或含硫五元杂单环基团，R¹、R²、R³ 和 R⁴ 是氢原子、低级烷基、苯基-低级烷基或苯基、R⁵ 是氢原子或低级烷基，R⁶ 是羧基、受保护的羧基、羟基或二(低级烷基)氨基，环 A 是取代或未取代的亚苯基，m 是 0 或 1，n 是 0 至 5 的整数、 条件是，当 m 为 0 时 (1) R¹ 至 R⁴ 中至少有一个是或/是苯基低级烷基或苯基、 (2) R¹ 至 R⁴ 中至少有一个是或/是低级烷基，且 R⁶ 是羟基，或 (3) 所有 R¹ 至 R⁴ 均为氢原子，且环 A 为取代的亚苯基、 或其药学上可接受的盐。所述衍生物（I）及其药学上可接受的盐具有强效的血小板聚集抑制活性。衍生物（I）可用于预防或治疗温血动物的血栓性疾病。本发明包括上述衍生物（I）的各种制备方法和包含治疗有效量的上述衍生物（I）的药物组合物。
• 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：——

  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.