5-Isobutyl-3-isopropyl-2-thioxo-imidazolidin-4-one | 86413-58-3

• 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-Isobutyl-3-isopropyl-2-thioxo-imidazolidin-4-one
• 英文别名: 5-(2-Methylpropyl)-3-propan-2-yl-2-sulfanylideneimidazolidin-4-one
• CAS: 86413-58-3
• 化学式: C₁₀H₁₈N₂OS
• mdl: MFCD24391245
• 分子量: 214.332
• InChiKey: UXTVQDWJYFTKRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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-Isobutyl-3-isopropyl-2-thioxo-imidazolidin-4-one 、 4-甲氧基苄胺 在 三乙胺 、 mercury dichloride 作用下， 反应 2.0h， 生成 5-isobutyl-3-isopropyl-5-((4-methoxybenzyl)amino)-2-thioxoimidazolidin-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：

  Isopropyldithiocarbamidsaeure-methylester 、 DL-亮氨酸 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以91%的产率得到5-Isobutyl-3-isopropyl-2-thioxo-imidazolidin-4-one
  参考文献：
  名称：

  Reactivity of Dithiocarbamic Esters: Methods for the Preparation of 3,5-Substituted 2-Thiohydantoins

  摘要：

  DOI：

  10.1055/s-1983-30349

文献信息

• BLOTNY, G., SYNTHESIS, BRD, 1983, N 5, 39
  作者：BLOTNY, G.

  DOI：——

  日期：——
• Reactivity of Dithiocarbamic Esters: Methods for the Preparation of 3,5-Substituted 2-Thiohydantoins
  作者：Grzegorz Błotny

  DOI：10.1055/s-1983-30349

  日期：——
• 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.