dehydroacetic acid thiosemicarbazone | 75843-20-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: dehydroacetic acid thiosemicarbazone
• 英文别名: [1-(4-Hydroxy-6-methyl-2-oxo-pyran-3-yl)ethylideneamino]thiourea；[1-(4-hydroxy-6-methyl-2-oxopyran-3-yl)ethylideneamino]thiourea
• CAS: 75843-20-8
• 化学式: C₉H₁₁N₃O₃S
• mdl: MFCD00141229
• 分子量: 241.271
• InChiKey: SHANQDPCTIFJEZ-UHFFFAOYSA-N

物化性质

• 沸点：
  378.4±52.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dehydroacetic acid thiosemicarbazone 在 羟基甲苯磺酰碘苯 作用下， 以 二氯甲烷 为溶剂， 以67%的产率得到去氢乙酸
  参考文献：
  名称：

  Pundeer, Rashmi; Chaudhri, Vishwas; Kinger, Mayank, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2007, vol. 46, # 5, p. 834 - 837

  摘要：

  DOI：
• 作为产物：
  描述：

  去氢乙酸 、 氨基硫脲 以 乙醇 为溶剂， 生成 dehydroacetic acid thiosemicarbazone
  参考文献：
  名称：

  某些1-（4-芳基噻唑-2-基）-1'-（芳基/杂芳基）-3,3'-二甲基-[4,5'-bi-1H-吡唑] -5-醇的合成及抗菌性能

  摘要：

  一系列十六个1-（4-芳基噻唑-2-基）-1'-（芳基/杂芳基）-3,3'-二甲基-[4,5'-bi-1 H-吡唑] -5-醇（由脱氢乙酸（DHA，1）起始，通过逐步形成硫代半脲（2），3-（1-（2-（4-芳基噻唑-2-基）肼基）乙基）-4-羟基合成7a – p） -6-甲基-2 H-吡喃-2-酮（4a – d）和1-（1-（4-芳基噻唑-2-基）-5-羟基-3-甲基-1 H-吡唑-4-基）1,3-丁烷（5a – d）的高收率。研究了合成的联吡唑7a – p对两种革兰氏阳性细菌菌株的体外抗菌和抗真菌活性。枯草芽孢杆菌（MTCC 441）和金黄色葡萄球菌（MTCC 7443），一种革兰氏阴性细菌菌株，即。大肠杆菌（MTCC 42）和两种真菌菌株，即。白色念珠菌（MTCC 183）和黑曲霉（MTCC 282）。发现化合物7a和7e比参考氟康唑表现出更好的针对黑曲霉的抑制活性。此外，标题化合物

  DOI：

  10.2298/jsc160310002m

文献信息

• Mononuclear ruthenium(III) complexes containing chelating thiosemicarbazones: Synthesis, characterization and catalytic property
  作者：N. Raja、R. Ramesh

  DOI：10.1016/j.saa.2009.11.044

  日期：2010.2

  Mononuclear ruthenium(III) complexes of the type [RuX(EPh3)2(L)] (E = P or As; X = Cl or Br; L = dibasic terdentate dehydroacetic acid thiosemicarbazones) have been synthesized from the reaction of thiosemicarbazone ligands with ruthenium(III) precursors, [RuX3(EPh3)3] (where E = P, X = Cl; E = As, X = Cl or Br) and [RuBr3(PPh3)2(CH3OH)] in benzene. The compositions of the complexes have been established

  [RuX（EPh 3）2（L）]型的单核钌（III）配合物（E = P或As； X = Cl或Br； L =二元叔齿脱氢乙酸硫代半氨基咔唑酮）已从硫代半碳鎓配体的反应中合成含钌（III）前体，[RuX 3（EPh 3）3 ]（其中E = P，X = Cl； E = As，X = Cl或Br）和[RuBr 3（PPh 3）2（CH 3OH）]在苯中。通过元素分析，磁化率测量，FT-IR，UV-vis和EPR光谱数据确定了复合物的组成。这些络合物是顺磁性的，在二氯甲烷中表现出强烈的d-d和电荷转移跃迁。配合物在LNT处显示出菱形的EPR光谱，这是低旋转扭曲的八面体钌（III）物种的典型特征。所有的配合物均具有氧化还原活性，并显示出不可逆的以金属为中心的氧化还原过程。络合物[RuCl（PPh 3）2（DHA-PTSC）]（5）在异丙醇/ KOH存在下用作酮转移氢化的催化剂，被发现是活性物质。
• Ruthenium(II) carbonyl complexes of dehydroacetic acid thiosemicarbazone: Synthesis, structure, light emission and biological activity
  作者：Sethuraman Kannan、M. Sivagamasundari、R. Ramesh、Yu Liu

  DOI：10.1016/j.jorganchem.2008.03.023

  日期：2008.6

  [RuHCl(CO)(B)(EPh3)2] (where E = As, B = AsPh3; E = P, B = PPh3, py, pip, or mor) and dehydroacetic acid thiosemicarbazone (abbreviated as H2dhatsc where H2 stands for the two dissociable protons) in benzene under reflux afford a series of new ruthenium(II) carbonyl complexes containing dehydroacetic acid thiosemicarbazone of general formula [Ru(dhatsc)(CO)(B)(EPh3)] (where E = As, B = AsPh3; E = P, B = PPh3, py,

  [RuHCl（CO）（B）（EPh 3）2 ]（其中E = As，B = AsPh 3； E = P，B = PPh 3，py，pip或mor）与脱氢乙酸硫代半碳zone的反应（缩写为如H 2 dhatsc（其中H 2代表苯中的两个可解离的质子），在回流下得到一系列含有通式[Ru（dhatsc）（CO）（B）（EPh 3）的脱氢乙酸硫代半脲的新钌（II）羰基配合物）]（其中E = As，B = AsPh 3； E = P，B = PPh 3，py，pip或mor； dhatsc =二元三齿三氢脱氢乙酸硫代半碳酰胺）。所有复合物均已通过元素分析，FT-IR，UV-Vis和1表征。1 H NMR光谱法。脱氢乙酸的硫代半碳酸盐表现为三齿双齿O，N，S供体，并通过脱氢乙酸的酚氧，硫代半碳胺的亚胺氮和硫醇硫与钌配位。在氯仿溶液中，所有络合物均表现出金属到配体的电荷转移跃迁（MLCT）。配合物之一[Ru（dhatsc）（CO）（PPh
• Synthesis and Antimicrobial Activity Evaluation of Novel 4-Thiazolidinones Containing a Pyrone Moiety
  作者：Rosa Nechak、Samia Aichouche Bouzroura、Yamina Benmalek、Lydia Salhi、Sophie P. Martini、Vincent Morizur、Elisabet Dunach、Bellara Nedjar Kolli

  DOI：10.1080/00397911.2014.970278

  日期：2015.1.17

  A series of thiosemicarbazones 3a-d and 4-thiazolidinones 5a-d, 7a-d, and 9a-h were synthesized and evaluated for their in vitro antimicrobial activity. Condensation of 3-acetyl-4-hydroxy-6-methyl-2H pyran-2-one1 (dehydroacetic acid) with thiosemicarbazide 2a-d in ethanol at room temperature yielded the thiosemicarbazones 3a-d. These compounds were exploited to synthesize the 4-thiazolidinones 5a-d via their reactions with ethyl 2-bromo propionate4. Derivatives 7a-d were prepared by reaction of the thiosemicarbazones 3a-d with phenyl bromoacetate 6. The 4-thiazolidinones 9a-h were obtained by treatment of compound 3a or 3c with maleimide derivatives 8a-d in refluxing ethanol, under sulfuric acid catalysis. All compounds were screened in vitro for their antibacterial and antifungal activities against five human pathogens microorganisms: Escherichia coli ATCC 25992, Pseudomonas aeruginosa ATCC 27852, Staphylococcus aureus ATCC 43300, Staphylococcus aureus ATCC 25923, and Candida albicans.
• Somogyi, Laszlo, Liebigs Annalen, 1995, # 4, p. 721 - 724
  作者：Somogyi, Laszlo

  DOI：——

  日期：——
• Synthesis and antimicrobial activities of some isoxazolyl thiazolyl pyrazoles
  作者：Satbir Mor、Rajni Mohil、Devinder Kumar、Munish Ahuja

  DOI：10.1007/s00044-011-9859-y

  日期：2012.11

  A series of isoxazolyl thiazolyl pyrazoles 5a-d was synthesized by multi-step process, starting from 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one (dehydroacetic acid, DHAA) 1. DHAA 1 was easily converted to thiosemicarbazone 2 which on reaction with alpha-bromoketones yielded thiazolyl hydrazones 3. Refluxing 3 in ethanol-acetic acid furnished 1-(5-hydroxy-3-methyl-1-substituted pyrazol-4-yl)-1,3-butanediones 4. Finally, the title compounds 5a-d were synthesized from 4 on treatment with hydroxylamine. The in vitro antimicrobial activity of compounds 3a-d, 4a-d and 5a-d were tested. Most of the synthesized compounds exhibited significant antibacterial and antifungal activities.