(E)-N,N-dimethyl-3-phenylprop-2-enethioamide | 96025-24-0

• 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: (E)-N,N-dimethyl-3-phenylprop-2-enethioamide
• 英文别名: (E)-N,N-dimethyl-3-phenylthioacrylamide；Thiozimtsaeurediethylamid
• CAS: 96025-24-0
• 化学式: C₁₁H₁₃NS
• 分子量: 191.297
• InChiKey: MHTMLEPNGADBPC-CMDGGOBGSA-N

物化性质

• 熔点：
  80-81 °C
• 沸点：
  283.4±33.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-N,N-dimethyl-3-phenylprop-2-enethioamide 950.0~1000.0 ℃ 、0.2 Pa 条件下， 以50%的产率得到1-methyl-4-phenyl-pyrrolidine-2-thione
  参考文献：
  名称：

  Cyclisation at very high temperature. Thermal transformations of N-alkyl and N, N-dialkyl amides of α,β-unsaturated acids into mono- and bicyclic heterocycles under FVT conditions

  摘要：

  Cyclisations of N-alkyl and N,N-dialkyl cinnamic amides to the corresponding pyrrolidin-2-ones under the conditions of flash vacuum thermolysis (FVT), are described. It was found that these reactions proceed at 950-1000 degrees C affording in various yields the mixtures of isomeric mono and bicyclic gamma-lactams, which were separated chromatographically and analysed by means of NMR spectroscopy. Two alternative mechanisms for the title process are proposed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.011
• 作为产物：
  描述：

  苯甲醛 、 Dimethylthiocarbamoylmethyl-phosphonic acid diethyl ester 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以62%的产率得到(E)-N,N-dimethyl-3-phenylprop-2-enethioamide
  参考文献：
  名称：

  Roy-Gourvennec, Sylvie Le; Masson, Serge, Synthesis, 1995, p. 1393 - 1396

  摘要：

  DOI：

文献信息

• Direct Catalytic Asymmetric Conjugate Addition of Terminal Alkynes to α,β-Unsaturated Thioamides
  作者：Ryo Yazaki、Naoya Kumagai、Masakatsu Shibasaki

  DOI：10.1021/ja105141x

  日期：2010.8.4

  Direct catalytic asymmetric conjugate addition of terminal alkynes to alpha,beta-unsaturated thioamides under proton transfer conditions is described. Soft Lewis acid/hard Brønsted base cooperative catalysis is crucial for simultaneous activation of terminal alkynes and thioamides, affording the beta-alkynylthioamides in a highly enantioselective manner. Control experiments suggested that the intermediate

  描述了在质子转移条件下将末端炔烃直接催化不对称共轭加成到 α、β-不饱和硫代酰胺。软路易斯酸/硬布朗斯台德碱协同催化对于同时活化末端炔烃和硫代酰胺至关重要，以高度对映选择性的方式提供 β-炔基硫代酰胺。对照实验表明中间体硫代酰胺铜烯醇化物可以作为布朗斯台德碱通过质子转移驱动催化循环。硫代酰胺官能团的发散转化突出了炔基化产物的合成效用。
• Threo selective cross aldol condensation with thioamide enolates generated by a michael addition of organometallics to unsaturated thioamides
  作者：Y. Tamaru、T. Hioki、Z. Yoshida

  DOI：10.1016/s0040-4039(01)81688-9

  日期：——

  Crotonothioamide, sorbothioamide, and cinnamothioamide undergo a threo selective aldol condensation via their enolates generated by a Michael addition of organometallics.

  巴豆硫代酰胺，山梨硫代酰胺和肉桂硫代酰胺通过迈克尔加成有机金属化合物生成的烯醇化物进行苏式选择性羟醛缩合。
• TAMARU YOSHINAO; HARADA TOSHIRO; YOSHIDA ZEN-ICHI, J. AMER. CHEM. SOC., 1979, 101, NO 5, 1316-1318
  作者：TAMARU YOSHINAO、 HARADA TOSHIRO、 YOSHIDA ZEN-ICHI

  DOI：——

  日期：——
• TAMARU, Y.;HIOKI, T.;YOSHIDA, Z., TETRAHEDERON LETT., 1984, 25, N 50, 5793-5796
  作者：TAMARU, Y.、HIOKI, T.、YOSHIDA, Z.

  DOI：——

  日期：——
• Cyclisation at very high temperature. Thermal transformations of N-alkyl and N, N-dialkyl amides of α,β-unsaturated acids into mono- and bicyclic heterocycles under FVT conditions
  作者：Stanisław Leśniak、Ryszard B. Nazarski、Beata Pasternak

  DOI：10.1016/j.tet.2009.06.011

  日期：2009.8

  Cyclisations of N-alkyl and N,N-dialkyl cinnamic amides to the corresponding pyrrolidin-2-ones under the conditions of flash vacuum thermolysis (FVT), are described. It was found that these reactions proceed at 950-1000 degrees C affording in various yields the mixtures of isomeric mono and bicyclic gamma-lactams, which were separated chromatographically and analysed by means of NMR spectroscopy. Two alternative mechanisms for the title process are proposed. (C) 2009 Elsevier Ltd. All rights reserved.