N-phenethyl-2-thiocarbamoylethanamide

• 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
• 英文名称: N-phenethyl-2-thiocarbamoylethanamide
• 英文别名: 3-amino-N-(2-phenylethyl)-3-sulfanylidenepropanamide
• 化学式: C₁₁H₁₄N₂OS
• 分子量: 222.311
• InChiKey: YLLOFAADHIGPAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  87.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-巯基丙酸乙酯 、 2-氰基苯乙基乙酰胺 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 11.0h， 以50%的产率得到N-phenethyl-2-thiocarbamoylethanamide
  参考文献：
  名称：

  High regioselectivity in the heterocyclization of β-oxonitriles to 4-oxothiazolidines: X-ray structure proof

  摘要：

  Base-catalyzed reactions of beta-oxonitriles 1 with diethyl mercaptosuccinate favour heterocyclization to afford 2-alkylidene-4-oxothiazolidines 3, rather than 2-alkylidene-4-oxo-1,3-thiazinanes 4. The observed regioselectivity is based on spectroscopic and experimental evidence, including a single-crystal X-ray structure determination. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)01146-3

文献信息

• Regioselective Synthesis and Spectral Characterization of Ethyl (Z)- and (E)-2-Alkylidene-4-oxothiazolidine-5-acetate Derivatives. Solvent Effects on the Z-E Isomerization
  作者：Rade Markovic、Marija Baranac

  DOI：10.3987/com-97-8094

  日期：——

  The title compounds containing an exocyclic double bond of exclusively the Z-configuration were prepared in anhydrous ethanol by the regioselective base catalyzed reaction of diethyl 2-mercaptobutanedioate with nitrile precursors possessing an acidic a-hydrogen. The H-1 NMR data indicating the presence of both geometrical isomers in primarily nonpolar media favoring the form are presented in terms of the solvent influence on intra- and intermolecular H-bonding and stereochemical outcome of the reaction.
• High regioselectivity in the heterocyclization of β-oxonitriles to 4-oxothiazolidines: X-ray structure proof
  作者：Rade Marković、Marija Baranac、Zdravko Džambaski、Milovan Stojanović、Peter J Steel

  DOI：10.1016/s0040-4020(03)01146-3

  日期：2003.9

  Base-catalyzed reactions of beta-oxonitriles 1 with diethyl mercaptosuccinate favour heterocyclization to afford 2-alkylidene-4-oxothiazolidines 3, rather than 2-alkylidene-4-oxo-1,3-thiazinanes 4. The observed regioselectivity is based on spectroscopic and experimental evidence, including a single-crystal X-ray structure determination. (C) 2003 Elsevier Ltd. All rights reserved.