乙酰胺,2-(丁基氨基)-N-苯基-2-硫代- | 180423-93-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 乙酰胺,2-(丁基氨基)-N-苯基-2-硫代-
• 英文名称: N^S-butyl-N^O-phenyl(thiooxamide)
• 英文别名: N(S)-butyl-N(O)-phenylthiooxamide；N-butylcarboanilidethioformamide；2-(butylamino)-N-phenyl-2-sulfanylideneacetamide
• CAS: 180423-93-2
• 化学式: C₁₂H₁₆N₂OS
• 分子量: 236.338
• InChiKey: NJATWDDKDAWSQT-UHFFFAOYSA-N

物化性质

• 熔点：
  58-60 °C(Solv: ethanol, 95% (64-17-5))
• 密度：
  1.167±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  环己胺 、 乙酰胺,2-(丁基氨基)-N-苯基-2-硫代- 反应 3.0h， 以57%的产率得到N(S)-cyclohexyl-N(O)-phenylthiooxamide
  参考文献：
  名称：

  Reactions of monothiooxamides with N-nucleophiles. Synthesis of 4,5-dihydroimidazole-2-carboxanilides

  摘要：

  A convenient procedure was developed for the preparation of 4,5-dihydroimidazole-2-carboxanilides by the reaction of monothiooxamides with ethylenediamine.

  DOI：

  10.1007/bf02496262
• 作为产物：
  描述：

  异氰酸苯酯 、 异氰酸正丁酯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 乙醚 为溶剂， 反应 0.5h， 以85%的产率得到乙酰胺,2-(丁基氨基)-N-苯基-2-硫代-
  参考文献：
  名称：

  Generation of Carbamoyl- and Thiocarbamoyllithium Synthons Having a Hydrogen(s) or an Aryl Group on the Nitrogen and Their Trapping with Carbonyl Electrophiles

  摘要：

  Dimetalated amides 1 (Y = O) were generated as the synthons of carbamoyllithiums 2 (Y = O) by the reaction of isocyanates with iBu2AlTenBu and a subsequent tellurium-lithium exchange reaction. A series of amide derivatives 3 (Y = O) were obtained by the trapping of dianion 1 with electrophiles. This transformation can be successfully applied to the generation and trapping of thiocarbamoyllithium synthons 1 (Y = S) as well as to the nucleophilic introduction of the parent carbamoyl moiety H2NC(O).

  DOI：

  10.1021/ja065078f

文献信息

• Synthesis of monothiooxamides
  作者：I. V. Zavarzin、V. N. Yarovenko、E. I. Chernoburova、M. M. Krayushkin

  DOI：10.1023/b:rucb.0000030819.80699.6e

  日期：2004.2

  A convenient method for the synthesis of monothiooxamides by the reaction of chloroacetamides with a solution of elemental sulfur in amines was developed.
• Structure ofN S-butyl-N O-phenyl(thiooxamide)
  作者：M. M. Krayushkin、L. G. Vorontsova、M. G. Kurella、I. V. Zavarzin、V. N. Yarovenko

  DOI：10.1007/bf01433998

  日期：1996.2

  The molecular and crystal structure of NS-butyl-NO-phenyl(thiooxamide) (1) has been established by X-ray structural analysis. The thiooxamide fragment and the phenyl ring are coplanar. The conformation of 1 is stabilized by NH...O and NH...S hydrogen bonds. No conjugation between the thioamide and the oxamide fragments of the molecule occurs. In the crystal, the centrosymmetrically related molecules 1 are linked in dimers through NH...O' intermolecular hydrogen bonds.
• Generation of Carbamoyl- and Thiocarbamoyllithium Synthons Having a Hydrogen(s) or an Aryl Group on the Nitrogen and Their Trapping with Carbonyl Electrophiles
  作者：Nobuaki Kambe、Toru Inoue、Takanobu Takeda、Shin-ichi Fujiwara、Noboru Sonoda

  DOI：10.1021/ja065078f

  日期：2006.10.1

  Dimetalated amides 1 (Y = O) were generated as the synthons of carbamoyllithiums 2 (Y = O) by the reaction of isocyanates with iBu2AlTenBu and a subsequent tellurium-lithium exchange reaction. A series of amide derivatives 3 (Y = O) were obtained by the trapping of dianion 1 with electrophiles. This transformation can be successfully applied to the generation and trapping of thiocarbamoyllithium synthons 1 (Y = S) as well as to the nucleophilic introduction of the parent carbamoyl moiety H2NC(O).
• Reactions of monothiooxamides with N-nucleophiles. Synthesis of 4,5-dihydroimidazole-2-carboxanilides
  作者：V. N. Yarovenko、S. A. Kosarev、I. V. Zavarzin、M. M. Krayushkin

  DOI：10.1007/bf02496262

  日期：1999.4

  A convenient procedure was developed for the preparation of 4,5-dihydroimidazole-2-carboxanilides by the reaction of monothiooxamides with ethylenediamine.