N-(4-Chloro-phenyl)-3-methylsulfanyl-propionamide | 73595-48-9

• 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-Chloro-phenyl)-3-methylsulfanyl-propionamide
• 英文别名: Cambridge id 5560931；N-(4-chlorophenyl)-3-methylsulfanylpropanamide
• CAS: 73595-48-9
• 化学式: C₁₀H₁₂ClNOS
• 分子量: 229.73
• InChiKey: IBASQHXFWMGXFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-Chloro-phenyl)-3-methylsulfanyl-propionamide 生成 p-chloro-N-(3-methylthio)propylaniline
  参考文献：
  名称：

  SATO, YASUNOBU;TOMITA, KUNIYUKI;KOBAYASHI, SHINSAKU

  摘要：

  DOI：
• 作为产物：
  描述：

  3-甲硫基丙酰氯 、 对氯苯胺 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 N-(4-Chloro-phenyl)-3-methylsulfanyl-propionamide
  参考文献：
  名称：

  Synthesis and Antiallergic Activity of Dimethyl-2-(phenylcarbamoyl)ethylsulfonium p-Toluenesulfonate Derivatives

  摘要：

  The derivatives of dimethyl-2-(phenylcarbamoyl)ethylsulfonium p-toluenesulfonates were synthesized and evaluated for antiallergic activity. The 2,3-dihydroxyethoxy group was introduced to the phenyl ring from the standpoint of lipophilicity and electronic effects of substituent. The IgE-induced rat passive cutaneous anaphylaxis (PCA) was inhibited by oral administration of several substituted 2-[(4-propoxyphenyl)carbamoyl]ethyldimethylsulfonium p-toluenesulfonate derivatives. Among them (+/-)-2-[4-(3-ethoxy-2-hydroxypropoxy)phenyl]-carbamoyl]ethyldimethylsulfonium p-toluenesulfonate (1a, IPD-1151T) was found to possess considerable activity in the PCA test, and it was launched as Suplatast tosilate in Japan.

  DOI：

  10.1021/jm970285z

文献信息

• Selective C(sp³)–S Bond Cleavage of Thioethers to Build Up Unsymmetrical Disulfides
  作者：Ke Yang、Yanqi Luo、Qingyue Hu、Mengjie Song、Junxiang Liu、Zhengyi Li、Bijin Li、Xiaoqiang Sun

  DOI：10.1021/acs.joc.3c01355

  日期：2023.10.6

  The selective C(sp3)–S bond cleavage of thioethers was first developed to prepare unsymmetrical disulfides by using electrophilic halogenation reagents. In this strategy, NBS (N-bromosuccinimide) achieves selective furfuryl C(sp3)–S bond cleavage of furfuryl alkylthioethers at room temperature. Meanwhile, NFSI (N-fluorobenzenesulfonimide) enables selective methyl C(sp3)–S bond cleavage of aryl and

  硫醚的选择性C(sp 3 )–S键断裂首先是通过使用亲电卤化试剂制备不对称二硫化物而开发的。在该策略中，NBS（N-溴代琥珀酰亚胺）在室温下实现了糠基烷基硫醚的选择性糠基C(sp 3 )-S键断裂。同时，NFSI（N-氟苯磺酰亚胺）能够在高温下选择性地裂解芳基和烷基甲基硫醚的甲基 C(sp 3 )-S 键。值得注意的是，底物范围研究表明，C-S键断裂的选择性顺序为糠基 C(sp 3 )–S > 苄基 C(sp 3 )–S > 烷基 C(sp 3 )–S > C(sp 2 )–S键。此外，这种实用且操作简单的策略还提供了一种重要的补充途径来获得具有优异官能团耐受性和中等至良好产率的各种不对称二硫化物。
• SATO, YASUNOBU;TOMITA, KUNIYUKI;KOBAYASHI, SHINSAKU
  作者：SATO, YASUNOBU、TOMITA, KUNIYUKI、KOBAYASHI, SHINSAKU

  DOI：——

  日期：——
• Synthesis and Antiallergic Activity of Dimethyl-2-(phenylcarbamoyl)ethylsulfonium <i>p</i>-Toluenesulfonate Derivatives
  作者：Yukio Tada、Ichiro Yamawaki、Shuichi Ueda、Hiroshi Matsumoto、Naosuke Matsuura、Mitsugi Yasumoto、Akihide Koda、Mikio Hori

  DOI：10.1021/jm970285z

  日期：1998.8.1

  The derivatives of dimethyl-2-(phenylcarbamoyl)ethylsulfonium p-toluenesulfonates were synthesized and evaluated for antiallergic activity. The 2,3-dihydroxyethoxy group was introduced to the phenyl ring from the standpoint of lipophilicity and electronic effects of substituent. The IgE-induced rat passive cutaneous anaphylaxis (PCA) was inhibited by oral administration of several substituted 2-[(4-propoxyphenyl)carbamoyl]ethyldimethylsulfonium p-toluenesulfonate derivatives. Among them (+/-)-2-[4-(3-ethoxy-2-hydroxypropoxy)phenyl]-carbamoyl]ethyldimethylsulfonium p-toluenesulfonate (1a, IPD-1151T) was found to possess considerable activity in the PCA test, and it was launched as Suplatast tosilate in Japan.