(Z)-5-(2-bromobenzylidene)hydantoin

• 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: (Z)-5-(2-bromobenzylidene)hydantoin
• 英文别名: (Z)-5-(2-bromobenzylidene)imidazolidine-2,4-dione；(5Z)-5-(2-bromobenzylidene)imidazolidine-2,4-dione；(5Z)-5-[(2-bromophenyl)methylidene]imidazolidine-2,4-dione
• 化学式: C₁₀H₇BrN₂O₂
• 分子量: 267.082
• InChiKey: IXOQHQRBVUQOTH-YVMONPNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  反式-BETA-苯乙烯硼酸 、 (Z)-5-(2-bromobenzylidene)hydantoin 在 吡啶 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以84%的产率得到(Z)-(5-(2-bromobenzylidene))-(E)-3-styrylhydantoin
  参考文献：
  名称：

  Cu-catalyzed C(sp²)–N-bond coupling of boronic acids and cyclic imides

  摘要：

  切割Ru。描述了一种通用的Cu催化方法，用于(E)-enimide形成。该过程温和实用，将环状酰胺和烯基硼酸偶联。该方法也可用于制备N-芳基酰胺。

  DOI：

  10.1039/d1cc04356k
• 作为产物：
  描述：

  5-[(2-Bromophenyl)methylidene]-2-sulfanylideneimidazolidin-4-one 在 tin(II) chloride dihdyrate 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以91%的产率得到(Z)-5-(2-bromobenzylidene)hydantoin
  参考文献：
  名称：

  SnCl₂·2H₂O: An Efficient Reagent for Selective and Direct Oxidative Desulfurization of Phenylmethylene-2-thiohydantoins to Corresponding Hydantoins

  摘要：

  DOI：

  10.1080/10426507.2010.525765

文献信息

• Anticonvulsant Activity of Phenylmethylenehydantoins:  A Structure−Activity Relationship Study
  作者：Jeyanthi Chinnappa Thenmozhiyal、Peter Tsun-Hon Wong、Wai-Keung Chui

  DOI：10.1021/jm030450c

  日期：2004.3.1

  Phenylmethylenehydantoins (PMHs) and their des-phenyl analogues were synthesized and evaluated for anticonvulsant activity using the maximal electroshock seizure (MES) assay. The phenyl rings of PMHs were substituted with a wide spectrum of groups, and the selection of substituents was guided by Craig's plot. Phenylmethylenehydantoins substituted with alkyl (2, 3, 5, 6, 12, 14), halogeno (35, 38, 41), trifluoromethyl (11), and alkoxyl (23) groups at the phenyl ring were found to exhibit good anticonvulsant activity with EDMES(2.5) ranging from 28 to 90 mg/kg. Substitution of polar groups such as -NO2, -CN, and -OH was found to be less active or inactive on PMHs. Replacement of the phenyl ring with heteroaromatic rings reduced or caused the loss of anticonvulsant activity. The study identified two PMHs, 14 (EDMES(2.5) = 28 +/- 2 mg/kg) and 12 (EDMES(2.5) = 39 4 mg/kg), to be the most active candidates of the series, which are comparable to phenytoin (55, EDMES(2.5) = 30 +/- 2 mg/kg) in their protection against seizure. Multivariate analysis performed on the whole series of 54 PMHs further supported the finding that the alkylated phenylmethylenehydantoins are the best acting compounds. The SAR model derived on the basis of 12 of the most active phenylmethylenehydantoins demonstrated good predicting ability (root-mean-square error of prediction (RMSEP) = 0.134; RMSEE = 0.057) and identified LUMO energy and the log P as critical parameters for their anticonvulsant activity.
• Cu-catalyzed C(sp²)–N-bond coupling of boronic acids and cyclic imides
  作者：Linn Neerbye Berntsen、Thomas Nordbø Solvi、Kristian Sørnes、David S. Wragg、Alexander H. Sandtorv

  DOI：10.1039/d1cc04356k

  日期：——

  Cu-t the Ru. A general Cu-catalyzed method for (E)-enimide-formation is described. The process is mild and practical, and couples cyclic imides and alkenylboronic acids. The method can also be used to prepare N-arylimides.

  切割Ru。描述了一种通用的Cu催化方法，用于(E)-enimide形成。该过程温和实用，将环状酰胺和烯基硼酸偶联。该方法也可用于制备N-芳基酰胺。
• SnCl₂·2H₂O: An Efficient Reagent for Selective and Direct Oxidative Desulfurization of Phenylmethylene-2-thiohydantoins to Corresponding Hydantoins
  作者：Ravi Kumar、Shashi Pandey、Shahnawaz Khan、Prem M. S. Chauhan

  DOI：10.1080/10426507.2010.525765

  日期：2011.7.1