(Z)-4-(4-fluorobenzylidene)-2-phenyl-1H-imidazol-5(4H)-one | 1391817-68-7

• 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: (Z)-4-(4-fluorobenzylidene)-2-phenyl-1H-imidazol-5(4H)-one
• 英文别名: (5Z)-2-phenyl-5-[(4-fluorophenyl)methylidene]-3,5-dihydro-4H-imidazol-4-one；2-phenyl-5-[1-(4-fluorophenyl)-meth-(Z)-ylidene]-3,5-dihydro-imidazol-4-one；(5z)-2-Phenyl-5-[(4-fluorophenyl)methylidene]-3,5-dihydro-4h-imidazol-4-one；(4Z)-4-[(4-fluorophenyl)methylidene]-2-phenyl-1H-imidazol-5-one
• CAS: 1391817-68-7
• 化学式: C₁₆H₁₁FN₂O
• 分子量: 266.275
• InChiKey: NDYLXWCAIVXJCQ-UVTDQMKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-[(1Z)-3-amino-1-(4-fluorophenyl)-3-oxoprop-1-en-2-yl]benzamide 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 (Z)-4-(4-fluorobenzylidene)-2-phenyl-1H-imidazol-5(4H)-one
  参考文献：
  名称：

  A Practical and Efficient Synthesis of 2,5-Disubstituted-3,5-dihydro-imidazol-4-ones from Oxazolones

  摘要：

  An alternative procedure for the synthesis of 2,5-disubstituted-3,5-dihydro-imidazol-4-ones from substituted oxazolones was evaluated. The initial oxazolone ring-opening reaction was examined with a variety of ammonia source compounds followed by the subsequent 3,5-dihydro-imidazol-4-one cyclization reaction, which was carried out with either an organic or inorganic base in aprotic solvents. In this article, we report the results of an efficient and straightforward procedure for the synthesis of 2,5-disubstituted-3,5-dihydro-imidazol-4-ones that gives satisfactory yield and quality.

  DOI：

  10.1080/00397911.2011.581406

文献信息

• Synthesis and biological testing of (5Z)-2-aryl-5-arylmethylidene-3,5-dihydro-4H-imidazol-4-ones as antimitotic agents
  作者：Anastasia A. Beloglazkina、Birgit Wobith、Elena S. Barskaia、Nikolay A. Zefirov、Alexander G. Majouga、Elena K. Beloglazkina、Nikolay V. Zyk、Sergei A. Kuznetsov、Olga N. Zefirova

  DOI：10.1007/s00044-016-1566-2

  日期：2016.6

  5-arylmethylidene fragment than on the 2-aryl ring in general. The cytotoxicities of the synthesized compounds were lower than those of the previously reported isomeric 2-aryl-4-benzoyl-imidazoles, and the basic structure–activity relationships in the isomeric pairs were different. Synthesized (5Z)-5-[(4-bromophenyl)methylidene]-2-(4-methylphenyl)-3,5-dihydro-4H-imidazol-4-one, which had the highest cytotoxicity

  与细胞蛋白微管蛋白和微管相互作用的化合物是抗有丝分裂剂的一种重要类型。据报道，一系列针对微管蛋白的2-芳基-4-苯甲酰基-咪唑具有很高的细胞毒性，因此，我们制备了一系列结构异构体，以作为抗有丝分裂剂进行评估。新型（Z）-2-芳基-5-芳基亚甲基-3,5-二氢-4 H的合成-咪唑-4-酮涉及取代的马尿酸与芳族醛的偶联。随后在尿素和乙酸铵存在下在微波辐射下将所得的恶唑酮转化为相应的咪唑酮。大多数化合物对人上皮癌细胞系A549的细胞毒性在亚微摩尔范围内，并且发现其对5-芳基亚甲基片段上的取代基的敏感性比通常对2-芳基环上的更为敏感。合成的化合物的细胞毒性低于以前报道的异构体2-芳基-4-苯甲酰基-咪唑，并且这些异构体对中的基本结构-活性关系不同。合成（5 Z）-5 - [（4-溴苯基）亚甲基] -2-（4-甲基苯基）-3,5-二氢-4- ħ -咪唑-4-酮，它具有最高的细胞毒性（IC 50  〜
• A Phosphine-Catalyzed Preparation of 4-Arylidene-5-imidazolones
  作者：Sandra Gabillet、Olivier Loreau、Simon Specklin、Evelia Rasalofonjatovo、Frédéric Taran

  DOI：10.1021/jo501922j

  日期：2014.10.17

  A simple and efficient method for constructing 4-arylidene-S-imidazolones was developed using a phosphine-catalyzed tandem umpolung addition and intramolecular cyclization of amidine pronucleophiles on arylpropiolates. The reaction offers a robust route to heterocycle analogues of the fluorescent protein chromophores.
• A Practical and Efficient Synthesis of 2,5-Disubstituted-3,5-dihydro-imidazol-4-ones from Oxazolones
  作者：Flavio Chavez、Caslin Pavy、Thomas Williamson、Thomas Cleary

  DOI：10.1080/00397911.2011.581406

  日期：2012.11.15

  An alternative procedure for the synthesis of 2,5-disubstituted-3,5-dihydro-imidazol-4-ones from substituted oxazolones was evaluated. The initial oxazolone ring-opening reaction was examined with a variety of ammonia source compounds followed by the subsequent 3,5-dihydro-imidazol-4-one cyclization reaction, which was carried out with either an organic or inorganic base in aprotic solvents. In this article, we report the results of an efficient and straightforward procedure for the synthesis of 2,5-disubstituted-3,5-dihydro-imidazol-4-ones that gives satisfactory yield and quality.