3-Benzyl-5-phenyl-2-thioxoimidazolidin-4-one | 256377-15-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 3-Benzyl-5-phenyl-2-thioxoimidazolidin-4-one
• 英文别名: 3-benzyl-5-phenyl-2-sulfanylideneimidazolidin-4-one
• CAS: 256377-15-8
• 化学式: C₁₆H₁₄N₂OS
• mdl: MFCD01817172
• 分子量: 282.366
• InChiKey: LVARGUTUGFHONI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Benzyl-5-phenyl-2-thioxoimidazolidin-4-one 、 2-(1-环己烯基)乙胺 在 三乙胺 、 mercury dichloride 作用下， 反应 2.0h， 生成 3-benzyl-5-((2-(cyclohex-1-en-yl)ethyl)amino)-5-phenyl-2-thioxioimidazolidin-4-one
  参考文献：
  名称：

  Unprecedented One-Pot Chemocontrolled Entry to Thioxoimidazolidinones and Aminoimidazolones: Synthesis of Kinase Inhibitor Leucettamine B

  摘要：

  A novel and highly chemoselective protocol for the construction of thioxoimidazolidinone and aminoimidazolone frameworks was explored, and the influence of the reaction conditions on product formation was studied to establish two distinct approaches for their selective formation. In this one-pot reaction, ambient temperature generally resulted in the formation of thioxoimidazolidinones, whereas microwave irradiation provided aminoimidazolones exclusively. An attempt to elucidate the observed chemoselectivity is described, and the products were confirmed by X-ray studies. One-pot synthesis toward Leucettamine B, a marine alkaloid, was achieved on the basis of this protocol.

  DOI：

  10.1021/co500152s
• 作为产物：
  描述：

  N-[2-(benzylamino)-4-phenyl-1,3-thiazol-5-yl]acetamide 在 盐酸 、 水 、 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以78%的产率得到3-Benzyl-5-phenyl-2-thioxoimidazolidin-4-one
  参考文献：
  名称：

  Synthesis of new 2,5-diamino-1,3-thiazole and 2-thiohydantoin derivatives by condensation of N-(2-Aryl-1-chloro-2-oxoethyl) carboxamides with thioureas

  摘要：

  N-(2-Aryl-1-chloro-2-oxoethyl) carboxamides react under mild conditions with thiourea, N-alkyl-and N-arylthioureas, and various N,N'-disubstituted thioureas, following the Hantzsch reaction scheme. The reactions are selective, and the resulting 2,5-diamino-1,3-thiazole derivatives undergo recyclization acid followed by hydrolysis to give substituted 2-thiohydantoins on heating with hydrochloric acid in ethanol.

  DOI：

  10.1134/s1070363208070268