(2Z)-1-phenyl-2-[(2-thioxoimidazolidin-1-yl)methylene]butane-1,3-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2Z)-1-phenyl-2-[(2-thioxoimidazolidin-1-yl)methylene]butane-1,3-dione
• 英文别名: (2Z)-1-phenyl-2-[(2-sulfanylideneimidazolidin-1-yl)methylidene]butane-1,3-dione
• 化学式: C₁₄H₁₄N₂O₂S
• 分子量: 274.343
• InChiKey: RBLYLODBYCQTAO-XFXZXTDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  81.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  呋喃甲酰氯 、 (2Z)-1-phenyl-2-[(2-thioxoimidazolidin-1-yl)methylene]butane-1,3-dione 在 吡啶 、 四甲基乙二胺 作用下， 以71%的产率得到(2Z)-1-phenyl-2-{[3-(2-furoyl)-2-thioxoimidazolidin-1-yl]methylene}butane-1,3-dione
  参考文献：
  名称：

  N-Acylated and N,N′-diacylated imidazolidine-2-thione derivatives and N,N′-diacylated tetrahydropyrimidine-2(1H)-thione analogues: Synthesis and antiproliferative activity

  摘要：

  Fifty-one acylthioureas (ATUs) incorporating imidazolidine-2-thione or its upper cyclohomologue were prepared by parallel synthesis and evaluated against a high number of human cancer cell lines for antiproliferative activity. ATUs 1o (3,5-dichlorobenzoyl), 1s (2-furoyl), 3s (2-furoyl) and 1t (2-thenoyl) displayed activity against leukemia, melanoma LOX IMVI, non-small cell lung NCI-H522, renal 786-0, CAKI-1, SN12C, UO-31 and breast MCF7, MDA-MB-435, T-47D cancer cell lines in the 0.3-9.7 mu M concentration range. Compound 14s exhibited selectivity for melanoma SK-MEL-5 (GI(50) < 5 nM); 1s for leukemia MOLT-4 (GI(50): 300 nM); 1q, 3b and 3q for renal cancer UO-31 (GI(50): 70200 nM); 8s, 9s for non-small cell lung cancer EKVX (GI(50): 300, 10 nM) and 3j for HOP-92 (GI(50): 700 nM) cell line. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.06.010
• 作为产物：
  描述：

  N-methyl-N-[(2-thioxoimidazolidin-1-yl)methylene]methanaminium chloride 、 1-苯基-1,3-丁二酮 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (2Z)-1-phenyl-2-[(2-thioxoimidazolidin-1-yl)methylene]butane-1,3-dione
  参考文献：
  名称：

  N-Acylated and N,N′-diacylated imidazolidine-2-thione derivatives and N,N′-diacylated tetrahydropyrimidine-2(1H)-thione analogues: Synthesis and antiproliferative activity

  摘要：

  Fifty-one acylthioureas (ATUs) incorporating imidazolidine-2-thione or its upper cyclohomologue were prepared by parallel synthesis and evaluated against a high number of human cancer cell lines for antiproliferative activity. ATUs 1o (3,5-dichlorobenzoyl), 1s (2-furoyl), 3s (2-furoyl) and 1t (2-thenoyl) displayed activity against leukemia, melanoma LOX IMVI, non-small cell lung NCI-H522, renal 786-0, CAKI-1, SN12C, UO-31 and breast MCF7, MDA-MB-435, T-47D cancer cell lines in the 0.3-9.7 mu M concentration range. Compound 14s exhibited selectivity for melanoma SK-MEL-5 (GI(50) < 5 nM); 1s for leukemia MOLT-4 (GI(50): 300 nM); 1q, 3b and 3q for renal cancer UO-31 (GI(50): 70200 nM); 8s, 9s for non-small cell lung cancer EKVX (GI(50): 300, 10 nM) and 3j for HOP-92 (GI(50): 700 nM) cell line. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.06.010

文献信息

• Unprecedented One-Pot Stereoselective Synthesis of Knoevenagel-Type Derivatives­ via in situ Condensation of <i>N</i>-Methyleniminium Salts of Ethylenethiourea­ and Ethyleneurea with Active Methylene Reagents
  作者：Angelo Ranise、Sara Cesarini、Andrea Spallarossa、Fernando Sancassan、Francesco Bondavalli、Olga Bruno、Silvia Schenone、Giulia Menozzi、Paola Fossa、Luisa Mosti

  DOI：10.1055/s-2007-983811

  日期：2007.8

  A facile stereoselective synthesis of Knoevenagel-type compounds 8 and 9 was accomplished through a one-pot two-step procedure. The reaction of ethylenethiourea ( 1) and ethyleneurea ( 2) with benzoyl chloride- N, N-dimethylformamide complex in N, N-dimethylformamide gave the corresponding isolable ternary N-methyleniminium chlorides 3 and 4, along with benzoic acid ( 5) as a byproduct. Hydrolysis

  Knoevenagel 型化合物 8 和 9 的简单立体选择性合成是通过一锅两步法完成的。亚乙基硫脲(1)和亚乙基脲(2)与苯甲酰氯-N,N-二甲基甲酰胺络合物在N,N-二甲基甲酰胺中的反应得到相应的可分离的三元N-亚甲基亚胺氯化物3和4，以及苯甲酸(5)作为副产品。盐 3 和 4 的水解产生 N-甲酰基衍生物 6 和 7，从而证实了 N-亚甲基亚胺结构。盐 3 和 4 在 5（程序 A）或 5 和三乙胺（1.5 equiv ) (程序 B)，得到 α,β-不饱和化合物 8 和 9。总产率从差到好。