3-Benzyl-5-isopropyl-2-thioxo-imidazolidin-4-one | 471271-03-1

• 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: 3-Benzyl-5-isopropyl-2-thioxo-imidazolidin-4-one
• 英文别名: 3-benzyl-5-propan-2-yl-2-sulfanylideneimidazolidin-4-one
• CAS: 471271-03-1
• 化学式: C₁₃H₁₆N₂OS
• mdl: MFCD01817171
• 分子量: 248.349
• InChiKey: MQHSXBDUDDFZEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.384
• 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-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 3-benzyl-5-isopropyl-5-(4-(methoxybenzyl)amino)-5-methyl-2-thioxoimidazolin-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：

  D,L-Val-OMe 、 异硫氰酸苯甲酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 3-Benzyl-5-isopropyl-2-thioxo-imidazolidin-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

文献信息

• Hydrogen bonded dimers vs. one-dimensional chains in 2-thiooxoimidazolidin-4-one (thiohydantoin) drug derivatives
  作者：Sushil Jha、Jon D. Silversides、Ross W. Boyle、Stephen J. Archibald

  DOI：10.1039/b924683e

  日期：——

  Hydantoins have been known as medicinally active compounds since the 1940s and thiohydantoin derivatives are currently undergoing clinical trials as potent androgen receptor antagonist drugs. Control of solid state properties including the formation of drug polymorphs is important to the pharmaceutical industry, and frequently results from different H-bonded motifs. N–H thiohydantoins show formation of H-bonded arrays in the solid state. Two novel and five known thiohydantoin derivatives were synthesised via reaction of alkyl isothiocyanates with amino acid methyl esters. X-Ray crystallographic data were obtained for all seven compounds showing that four of the structures contain hydrogen bonded dimeric units linked via N–H⋯S interactions and three of the structures have N–H⋯O linked H-bonded chains.

  自20世纪40年代以来，海因妥因（hydantoins）一直被认为具有药物活性，而硫代海因妥因衍生物目前正处于临床试验阶段，作为强效的雄激素受体拮抗剂药物。控制固态性质，包括药物多晶型的形成，对制药行业至关重要，并且通常源于不同的氢键模式。N-H硫代海因妥因在固态中显示出氢键阵列的形成。通过异硫氰酸烷基酯与氨基酸甲酯的反应合成了两种新型及五种已知的硫代海因妥因衍生物。对所有七种化合物获得了X射线晶体学数据，显示其中四种结构含有通过N-H⋯S相互作用链接的氢键二聚体单元，而另外三种结构则具有通过N-H⋯O链接的氢键链。