2-phenylthiomethylacrylamide | 135056-66-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-phenylthiomethylacrylamide
• 英文别名: 2-Propenamide, 2-[(phenylthio)methyl]-；2-(phenylsulfanylmethyl)prop-2-enamide
• CAS: 135056-66-5
• 化学式: C₁₀H₁₁NOS
• 分子量: 193.269
• InChiKey: ZOMMWPLFZRGADQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-((苄氧基)羰基)-3-碘-L-丙氨酸甲酯 、 2-phenylthiomethylacrylamide 在 铜 、 锌 作用下， 以 乙醇 为溶剂， 反应 7.0h， 以50%的产率得到(+)-methyl 2-N-benzyloxycarbonylamino-5-carboxamidohex-5-enate
  参考文献：
  名称：

  A Synthetic Approach to Carbocyclic Sinefungin

  摘要：

  An approach to an asymmetric synthesis of carbocyclic sinefungin (cSF) 2 is proposed. The sequence, which uses an original radical based chemistry for C-C bond formation, led to the immediate precursor 18 of the protected desired compound. While the overall yield is modest, it is noticeable that only a limited number of steps are needed to obtain the target compound.

  DOI：

  10.1080/07328319808004308
• 作为产物：
  描述：

  ethyl 2-phenylthiomethylacrylate 在 三甲基铝 、 氯化铵 作用下， 生成 2-phenylthiomethylacrylamide
  参考文献：
  名称：

  Barton, Derek H. R.; Gero, Stephane D.; Quiclet-Sire, Beatrice, Journal of the Chemical Society. Perkin transactions I, 1991, # 5, p. 981 - 985

  摘要：

  DOI：

文献信息

• The invention of radical reactions. Part XXV. A convenient method for the synthesis of the acyl derivatives of N-hydroxypyridine-2-thione
  作者：Derek H.R. Barton、Mohammad Samadi

  DOI：10.1016/s0040-4020(01)88249-1

  日期：1992.1

  Treatment of the readily available di-N-oxide- of 2-thiopyridine disulfide 6 with tributylphosphine in the presence of a carboxylic acid provides a convenient and high yielding synthesis of the acyl derivatives 2 of N-hydroxy-2-thio-pyridone. Application of this procedure to the acids 17 and 18 gave, after irradiation in the presence of t-butylthiol, the desired decarboxylated derivatives in high (>90%)

  容易获得的2-硫代吡啶二硫化物的二-N-氧化物的治疗6与三丁基膦在羧酸的存在提供的酰基衍生物的方便和高产合成2 N-羟基-2-硫代吡啶酮。在叔丁基硫醇存在下进行辐射后，将该方法应用于酸17和18，以高产率（＞ 90％）得到所需的脱羧衍生物。
• Total Synthesis of the Thymidine Analogue of Sinefungin
  作者：Derek H. R. Barton、Stephan D. Gero、Guillerm Negron、Béatrice Quiclet-Sire、Mohammad Samadi、Claire Vincent

  DOI：10.1080/15257779508009744

  日期：1995.10

  The carbon skeleton of ''Sinethymidin'' 4 was constructed by two radical coupling reaction. The first step was a coupling of the radical derived from 2 and the unsaturated amide 5. The olefin 6 thus obtained was added to the radical derived from the known N-hydroxy-2-thiopyridinone aspartic ester. ''Sinethymidin'', tested for its antileismanial effect, was devoid of activity.
• BARTON, DEREK H. R.;GERO, STEPHANE D.;QUICLET-SIRE, BEATRICE;SAMADI, MOHA+, J. CHEM. SOC. PERKIN TRANS. 1,(1991) N, C. 981-985
  作者：BARTON, DEREK H. R.、GERO, STEPHANE D.、QUICLET-SIRE, BEATRICE、SAMADI, MOHA+

  DOI：——

  日期：——