3-Methylsulfanyl-N-(4-trifluoromethyl-phenyl)-propionamide | 25617-47-4

• 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: 3-Methylsulfanyl-N-(4-trifluoromethyl-phenyl)-propionamide
• 英文别名: 3-methylsulfanyl-N-[4-(trifluoromethyl)phenyl]propanamide
• CAS: 25617-47-4
• 化学式: C₁₁H₁₂F₃NOS
• 分子量: 263.284
• InChiKey: SAVXLINKDFESKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-Methylsulfanyl-N-(4-trifluoromethyl-phenyl)-propionamide 在 Selectfluor 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以70%的产率得到N-(4-(trifluoromethyl)phenyl)acrylamide
  参考文献：
  名称：

  无金属的C–S键裂解可得到N-取代的丙烯酰胺和β-氨基丙酰胺

  摘要：

  已经建立了无金属的C-S键裂解过程，可在Selectfluor存在下构建N取代的丙烯酰胺和β-氨基丙酰胺衍生物。

  DOI：

  10.1002/ejoc.201900960
• 作为产物：
  描述：

  对三氟甲基苯胺 、 3-甲硫基丙酰氯 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 3-Methylsulfanyl-N-(4-trifluoromethyl-phenyl)-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

• 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.
• Metal-Free C-S Bond Cleavage to Access <i>N</i> -Substituted Acrylamide and β-Aminopropanamide
  作者：Ke Yang、Yi Li、Zhiyan Ma、Long Tang、Yue Yin、Hao Zhang、Zhengyi Li、Xiaoqiang Sun

  DOI：10.1002/ejoc.201900960

  日期：2019.9.8

  The metal‐free C–S bond cleavage process has been established to construct N‐substituted acrylamide and β‐aminopropanamide derivatives in the presence of Selectfluor.

  已经建立了无金属的C-S键裂解过程，可在Selectfluor存在下构建N取代的丙烯酰胺和β-氨基丙酰胺衍生物。