5-benzyl-3-butyl-2-thioxoimidazolidin-4-one

• 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: 5-benzyl-3-butyl-2-thioxoimidazolidin-4-one
• 英文别名: 5-Benzyl-3-butyl-2-sulfanylideneimidazolidin-4-one；5-benzyl-3-butyl-2-sulfanylideneimidazolidin-4-one
• 化学式: C₁₄H₁₈N₂OS
• 分子量: 262.376
• InChiKey: MKPVDRUBTPUYQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  5-benzyl-3-butyl-2-thioxoimidazolidin-4-one 、 2-(1-环己烯基)乙胺 在 三乙胺 、 mercury dichloride 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 (Z)-4-bezylidene-1-butyl-2-((2-(cyclohex-1-en-yl)ethyl)amino)-1H-imidazol-5(4H)-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-甲基-N-叔丁氧羰基-D-苯丙氨酸 在 4-二甲氨基吡啶 、 二乙胺 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 27.25h， 生成 5-benzyl-3-butyl-2-thioxoimidazolidin-4-one
  参考文献：
  名称：

  Microwave-Assisted Synthesis of 3,5-Disubstituted Thiohydantoins Using Functional Ionic Liquid as Soluble Support

  摘要：

  A new approach for the syntheses of 3,5-disubstituted thiohydantoins was described using functionalized ionic liquid as soluble support. The products were obtained in good yields and purities after cyclization-cleavage from the ionic-liquid-supported under microwave irradiation, the ionic-liquid-supported species can there be purified from the reaction mixture by simple washing, and no chromatographic purification were needed during the synthesis.

  DOI：

  10.3987/com-10-12086

文献信息

• Unprecedented One-Pot Chemocontrolled Entry to Thioxoimidazolidinones and Aminoimidazolones: Synthesis of Kinase Inhibitor Leucettamine B
  作者：Manikandan Selvaraju、Chung-Ming Sun

  DOI：10.1021/co500152s

  日期：2015.3.9

  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.
• Microwave-Assisted Synthesis of 3,5-Disubstituted Thiohydantoins Using Functional Ionic Liquid as Soluble Support
  作者：Chen Zhuo、Dong Xian、Xie Hui、Li Mei

  DOI：10.3987/com-10-12086

  日期：——

  A new approach for the syntheses of 3,5-disubstituted thiohydantoins was described using functionalized ionic liquid as soluble support. The products were obtained in good yields and purities after cyclization-cleavage from the ionic-liquid-supported under microwave irradiation, the ionic-liquid-supported species can there be purified from the reaction mixture by simple washing, and no chromatographic purification were needed during the synthesis.