(Z)-5-(4-methylbenzylidene)-2-(piperidin-1-yl)thiazol-4(5H)-one | 1347744-95-9

• 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: (Z)-5-(4-methylbenzylidene)-2-(piperidin-1-yl)thiazol-4(5H)-one
• 英文别名: (Z)-5-(4-methyl-benzylidene)-2-piperidin-1-yl-thiazol-4-one；5-(4-Methyl-benzylidene)-2-piperidin-1-yl-thiazol-4-one；(5Z)-5-[(4-methylphenyl)methylidene]-2-piperidin-1-yl-1,3-thiazol-4-one
• CAS: 1347744-95-9
• 化学式: C₁₆H₁₈N₂OS
• 分子量: 286.398
• InChiKey: XCHNLICRAHQEIE-KAMYIIQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  58
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  哌啶 、 罗丹宁 、 对甲基苯甲醛 在 silica-based substituted pyridine catalyst 7 作用下， 以 乙醇 、 水 为溶剂， 反应 2.02h， 以90%的产率得到(Z)-5-(4-methylbenzylidene)-2-(piperidin-1-yl)thiazol-4(5H)-one
  参考文献：
  名称：

  Rapid and straightforward one-pot expeditious synthesis of 2-amino-5-alkylidene-thiazol-4-ones at room temperature

  摘要：

  A new methodology has been developed towards the room temperature synthesis of novel 2-amino-5-alkylidenethiazol-4-ones from aldehydes, amines and rhodanine in one-pot. A heterogeneous dipolar catalyst has been utilized for this reaction. The unique properties of this catalyst effectively synthesize such compounds at room temperature in contrast to all earlier reports. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.09.090

文献信息

• Synthesis of novel 5-arylidenethiazolidinones with apoptotic properties via a three component reaction using piperidine as a bifunctional reagent
  作者：Chandramohan Bathula、Sayantan Tripathi、Ramprasad Srinivasan、Kunal Kumar Jha、Arnab Ganguli、G. Chakrabarti、Shailja Singh、Parthapratim Munshi、Subhabrata Sen

  DOI：10.1039/c6ob01257d

  日期：——

  The synthesis of a new library of 5-arylidenethiazolidinone compounds using an efficient three component reaction with thiazolidine-2,4-dione, piperidine and appropriate aldehydes is reported. This reaction is excellently high yielding, tolerant towards a variety of aldehydes and provides access to these compounds in a single step (in comparison to low yielding multistep syntheses reported in the literature)

  据报道，通过与噻唑烷-2,4-二酮，哌啶和适当的醛类进行有效的三组分反应，合成了一个新的5-芳基吡啶并恶唑烷酮化合物库。该反应具有极高的产率，对多种醛具有耐受性，并且一步即可获得这些化合物（与文献中报道的低产率的多步合成相比）。反应完成后，所需产物从反应混合物中沉淀出来，通过过滤分离，并通过洗涤和重结晶纯化。这些化合物显示出对人乳腺癌细胞（MCF7和MDA）的抗增殖活性。表型分析建立了活性最高的化合物17i（EC 50= 4.52μM）作为凋亡因子。一种新颖的化学蛋白质组学方法鉴定β肌动蛋白样蛋白2，γ-烯醇化酶和推定的细胞结合配偶体巨噬细胞迁移抑制因子（MMIF）17I。
• Rapid and straightforward one-pot expeditious synthesis of 2-amino-5-alkylidene-thiazol-4-ones at room temperature
  作者：Chhanda Mukhopadhyay、Suman Ray

  DOI：10.1016/j.tetlet.2011.09.090

  日期：2011.11

  A new methodology has been developed towards the room temperature synthesis of novel 2-amino-5-alkylidenethiazol-4-ones from aldehydes, amines and rhodanine in one-pot. A heterogeneous dipolar catalyst has been utilized for this reaction. The unique properties of this catalyst effectively synthesize such compounds at room temperature in contrast to all earlier reports. (C) 2011 Elsevier Ltd. All rights reserved.