2-{(E)-[(Z)-3,4-dihydronaphthalen-1(2H)-ylidene]-hydrazono}-thiazolidin-4-one | 1321762-52-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-{(E)-[(Z)-3,4-dihydronaphthalen-1(2H)-ylidene]-hydrazono}-thiazolidin-4-one
• 英文别名: (Z)-2-((E)-(3,4-dihydronaphthalen-1(2H)ylidene)hydrazono)thiazolidin-4-one；2-[(E)-3,4-dihydro-2H-naphthalen-1-ylidenehydrazinylidene]-1,3-thiazolidin-4-one
• CAS: 1321762-52-0
• 化学式: C₁₃H₁₃N₃OS
• 分子量: 259.332
• InChiKey: OCPUHAUPNYETAY-RVDMUPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  79.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,4-二氢-1(2H)-萘酮 在 盐酸 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 2-{(E)-[(Z)-3,4-dihydronaphthalen-1(2H)-ylidene]-hydrazono}-thiazolidin-4-one
  参考文献：
  名称：

  Efficient synthesis, X-ray diffraction study and antimicrobial activity of some novel thiazolidin-4-ones and perhydro-1,3-thiazin-4-ones

  摘要：

  摘要：从1-四氢萘衍生的硫脲酮1与氯乙酸和溴丙酸在N-甲基吡啶盐酸对甲苯磺酸盐（一种离子液体）存在下缩合，得到相应的2-取代的4-噻唑烷酮2。硫脲酮1与3-氯丙酸反应，产率优异地生成过氢-1,3-噻唑烷-4-酮3。化合物2和3的结构基于元素分析、红外、核磁共振和质谱数据得到确认。报道了化合物2a的X射线晶体学研究。对化合物1-3进行了抗菌活性研究，针对革兰氏阳性细菌枯草芽孢杆菌、金黄色葡萄球菌，以及革兰氏阴性细菌铜绿假单胞菌、大肠杆菌，以及真菌黑曲霉、白念珠菌和烟曲霉。发现噻唑烷酮比过氢噻唑烷酮更活跃。

  DOI：

  10.1515/hc-2012-0180

文献信息

• Efficient synthesis of 2,4-disubstituted thiazoles and 2-substituted 4-thiazolidinones under solvent free conditions
  作者：Deepika Gautam、Poonam Gautam、Ram P. Chaudhary

  DOI：10.1515/hc.2011.027

  日期：2011.1.1

  Condensation of thiosemicarbazones 2 derived from 1-tetralones (1) with chloroacetic acid in presence of N-methylpyridinium tosylate (an ionic liquid) yields 2-substituted-4-thiazolidinones 3. The reaction of 2 with alpha-halo carbonyl compounds at room temperature under grinding conditions yields 2,4-disubstituted thiazoles 4 in excellent yields. The structures of compounds 2-4 have been established on the basis of elemental analysis, IR, NMR and mass spectral data.
• Efficient synthesis, X-ray diffraction study and antimicrobial activity of some novel thiazolidin-4-ones and perhydro-1,3-thiazin-4-ones
  作者：Deepika Gautam、Poonam Gautam、Ram P. Chaudhary

  DOI：10.1515/hc-2012-0180

  日期：2013.3.1

  Condensations of thiosemicarbazones 1 derived from 1-tetralones with chloroacetic acid and 2-bromopropionic acid in the presence of N-methylpyridinium p-toluenesulfonate (an ionic liquid) yield the corresponding 2-substituted 4-thiazolidinones 2. The reactions of 1 with 3-chloropropionic acid afford perhydro-1,3-thiazinan-4-ones 3 in excellent yields. The structures of compounds 2 and 3 were established on the basis of elemental analysis, IR, NMR and mass spectral data. X-Ray crystallographic studies of compound 2a are reported. Compounds 1–3 were investigated for antimicrobial activities against Bacillus subtilis, Staphylococcus aureus (Gram-positive bacteria) and Pseudomonas aeruginosa, Escherichia coli (Gram-negative bacteria) and the fungi Aspergillus niger, Candida albicans and Aspergillus fumigatus. Thiazolidin-4-ones were found to be more active than perhydrothiazin-4-ones.

  摘要：从1-四氢萘衍生的硫脲酮1与氯乙酸和溴丙酸在N-甲基吡啶盐酸对甲苯磺酸盐（一种离子液体）存在下缩合，得到相应的2-取代的4-噻唑烷酮2。硫脲酮1与3-氯丙酸反应，产率优异地生成过氢-1,3-噻唑烷-4-酮3。化合物2和3的结构基于元素分析、红外、核磁共振和质谱数据得到确认。报道了化合物2a的X射线晶体学研究。对化合物1-3进行了抗菌活性研究，针对革兰氏阳性细菌枯草芽孢杆菌、金黄色葡萄球菌，以及革兰氏阴性细菌铜绿假单胞菌、大肠杆菌，以及真菌黑曲霉、白念珠菌和烟曲霉。发现噻唑烷酮比过氢噻唑烷酮更活跃。