(5Z)-2-thioxo-3-allyl-2-[(5'-bromopyridine-2-yl)methylene]-imidazole-4(4H)-one | 1610846-81-5

• 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: (5Z)-2-thioxo-3-allyl-2-[(5'-bromopyridine-2-yl)methylene]-imidazole-4(4H)-one
• CAS: 1610846-81-5
• 化学式: C₁₂H₁₀BrN₃OS
• 分子量: 324.201
• InChiKey: YDVQCMHAHHVBRL-POHAHGRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  45.23
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (5Z)-2-thioxo-3-allyl-2-[(5'-bromopyridine-2-yl)methylene]-imidazole-4(4H)-one 、 1,2-二溴乙烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以62%的产率得到(5Z,5'Z)-2,2'-(ethane-1,2-diylsulfanyldiyl)bis[5-(5'-bromo-pyridine-2-ylmethylene)-3-allyl-3,5-dihydro-4Н-imidazole-4-one]
  参考文献：
  名称：

  Conversion of 2-thiohydantoins and their derivatives to the corresponding hydantoins in the processes of complexation reactions with copper(II) chloride dihydrate

  摘要：

  The treatment of 5-pyridylmethylene-substituted 2-thiohydantoins or 2-alkylthio-3,5-dihydro-4H-imidazole-4-ones with CuCl(2)2H(2)O affords the mononuclear or polymeric copper(II) complexes of the corresponding hydantoins. A presumable mechanism of hydantoin moiety formation involves Lewis acid catalyzed nucleophilic substitution of a sulfur-containing leaving group in the organic ligand by a water molecule from CuCl2H2O. The copper complexes Cu(L-1-H)Cl(H2O) (7; L-1 = (Z)-3-allyl-5-(pyridine-2-ylmethylene)imidazole-2,4(4H)-dione) and Cu(L-2-H)(2) (9; L-2 = Z)-3-allyl-5-(5'-bromo-pyridine-2-ylmethylene)imidazole-2,4(4H)-dione) were characterized by X-ray diffraction. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2014.03.045
• 作为产物：
  描述：

  3-丙-2-烯基-2-巯基咪唑烷-4-酮 、 5-溴-2-吡啶甲醛 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以78%的产率得到(5Z)-2-thioxo-3-allyl-2-[(5'-bromopyridine-2-yl)methylene]-imidazole-4(4H)-one
  参考文献：
  名称：

  Conversion of 2-thiohydantoins and their derivatives to the corresponding hydantoins in the processes of complexation reactions with copper(II) chloride dihydrate

  摘要：

  The treatment of 5-pyridylmethylene-substituted 2-thiohydantoins or 2-alkylthio-3,5-dihydro-4H-imidazole-4-ones with CuCl(2)2H(2)O affords the mononuclear or polymeric copper(II) complexes of the corresponding hydantoins. A presumable mechanism of hydantoin moiety formation involves Lewis acid catalyzed nucleophilic substitution of a sulfur-containing leaving group in the organic ligand by a water molecule from CuCl2H2O. The copper complexes Cu(L-1-H)Cl(H2O) (7; L-1 = (Z)-3-allyl-5-(pyridine-2-ylmethylene)imidazole-2,4(4H)-dione) and Cu(L-2-H)(2) (9; L-2 = Z)-3-allyl-5-(5'-bromo-pyridine-2-ylmethylene)imidazole-2,4(4H)-dione) were characterized by X-ray diffraction. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2014.03.045