methyl acetoacetate thiosemicarbazone | 26697-97-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl acetoacetate thiosemicarbazone
• 英文别名: methylacetoacetate thiosemicarbazone；Acetessigsaeuremethylesterthiosemicarbazon；Methyl 3-(carbamothioylhydrazinylidene)butanoate
• CAS: 26697-97-2
• 化学式: C₆H₁₁N₃O₂S
• 分子量: 189.238
• InChiKey: NPVMLXOOFRGSML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trichlorotris(triphenylarsine)ruthenium(III) 、 methyl acetoacetate thiosemicarbazone 以 苯 为溶剂， 以85%的产率得到
  参考文献：
  名称：

  SYNTHESIS, CHARACTERISATION, CATALYTIC, AND BIOCIDAL STUDIES OF RUTHENIUM(III) COMPLEXES WITH THIOSEMICARBAZONES OF β-DIKETOESTERS

  摘要：

  Ruthenium(III) complexes, [RuX(EPh3)(2)(L)] (X=Cl, Br; E=P, As; L=tridentate Schiff base dianion), have been synthesised by reacting [RuCl3(PPh3)(3)], [RuCl3(AsPh3)(3)] or [RuBr3(AsPh3)(3)] with thiosemicarbazones of methyl- and ethyl acetoacetates. All of the new complexes have been characterised by elemental analyses, IR, electronic, EPR and cyclic voltammetric data and an octahedral structure has been tentatively proposed. The ruthenium(III) complexes were found to be effective catalysts for the oxidation of alcohols to the corresponding carbonyl compounds in the presence of N-methylmorpholine-N-oxide (NMO) as a co-oxidant. The Schiff bases and the new complexes have been tested for the in vitro growth inhibitory activity against the bacteria E. Coli, Bacillus sp. and Pseudomonas sp.

  DOI：

  10.1081/sim-120013023

文献信息

• Rhenium(I)-Induced Cyclization of Thiosemicarbazones Derived from β-Keto Esters
  作者：Rosa Carballo、José S. Casas、Emilia García-Martínez、Gumersindo Pereiras-Gabián、Agustín Sánchez、José Sordo、Ezequiel M. Vázquez-López

  DOI：10.1021/ic030154q

  日期：2003.10.1

  the tetrameric complexes fac-[Re(pyz(A))(CO)(3)](4) and fac-[Re(pyz(B))(CO)(3)](4), and fac-[Re(pyz(B))(CO)(3)(H(2)O)] (where Hpyz(A) and Hpyz(B) are pyrazolones derived by cyclization of H(2)L(A) and H(2)L(B), respectively). The cyclization reactions were monitored by (1)H NMR spectroscopy and the complexes isolated were identified by elemental analysis, mass spectrometry, IR and (1)H NMR spectroscopy

  乙酰乙酸甲酯和2-甲基乙酰乙酸乙酯的硫代半咔唑酮（分别为H（2）L（A）和H（2）L（B））与[ReX（CO）（5）]和[ReX（CO）（3） （CH（3）CN）（2）]（X = Cl，Br）在各种实验条件下进行了探索。除了加合物fac- [ReX（CO）（3）（H（2）L）]（其中is与三个羰基，X阴离子和N，S-双齿硫代半碳酰胺配体配位）外，还存在以下配合物还分离了：fac- [ReBr（CO）（3）（Hpyz（B））]，四聚体复合物fac- [Re（pyz（A））（CO）（3）]（4）和fac- [Re （pyz（B））（CO）（3）]（4）和fac- [Re（pyz（B））（CO）（3）（H（2）O）]（其中Hpyz（A）和Hpyz （B）是分别通过H（2）L（A）和H（2）L（B）的环化衍生的吡唑啉酮。通过（1）H NMR光谱监测环化反应，并通过元素分析，质谱，IR和（1）H N
• Casas, Jose S.; Castanno, Maria V.; Castellano, Eduardo E., European Journal of Inorganic Chemistry
  作者：Casas, Jose S.、Castanno, Maria V.、Castellano, Eduardo E.、Garcia-Tasende, Maria S.、Sanchez, Agustin、et al.

  DOI：——

  日期：——
• Structural and antitumour studies of metal complexes with thiosemicarbazones of β-diketoesters
  作者：S. Jayasree、K.K. Aravindakshan

  DOI：10.1016/s0277-5387(00)88210-8

  日期：1993.5

  The reactions of thiosemicarbazones of methyl- and ethylacetoacetates (MatH-2 and EatH-2, respectively) with the acetates of manganese(II), cobalt(II), nickel(II), copper(II), zinc(II) and cadmium(II) gave solid complexes, which were characterized by various physicochemical methods such as microanalyses, magnetic measurements and ESR, UV-vis, IR and NMR spectral studies. They were found to be of the following general formulae: [M(LH)2], where M = Mn(II), Co(II), Ni(II) or Cd(II) and LH = monoanions, MatH or EatH; [Cu(L)] and [Zn(L)(H2O)], where L = dianions, Mat or Eat. The thiosemicarbazones and their cobalt(II) and copper(II) compLexes were screened for their possibLe antitumour activity.
• Metal-Induced Cyclization of Thiosemicarbazones Derived from β-Keto Amides and β-Keto Esters:  Open-Chain and Cyclized Ligands in Zinc(II) Complexes
  作者：José S. Casas、María V. Castaño、Eduardo E. Castellano、Javier Ellena、María S. García-Tasende、Ángeles Gato、Agustín Sánchez、Luisa M. Sanjuán、José Sordo

  DOI：10.1021/ic0111942

  日期：2002.3.1

  The reactions of Zn(OAc)(2) with acetoacetanilide, methyl acetoacetate, o-acetoacetanisidide, and ethyl 2-methylacetoacetate thiosemicarbazones (HTSC1, HTSC2, HTSC3, and HTSC4, respectively) were explored in methanol. With HTSC1, HTSC2, and HTSC3, following isolation of the corresponding zinc(II) thiosemicarbazonates [Zn(TSCx)(2)] (x = 1, 2, 3), the mother liquors afforded pyrazolonate complexes [ZnL21(H2O)] (HL1 = 2,5-dihydro-3-methyl-5-oxo-1H-pyrazole-1-carbothioamide) that had been formed by cyclization of the corresponding TSC-. The reaction of HTSC4 with zinc(II) acetate gave only the pyrazolonate complex [ZnL22(H2O)] (HL2 = 2,5-dihydro-3,4-dimethyl5-oxo-1H-pyrazole-1-carbothioamide). All compounds were studied by IR and NMR spectroscopy, and HTSC3, [Zn(TSC3)(2)]-DMSO, [ZnL21(H2O)](.)2DMSO, and [ZnL22(H2O)](.)2DMSO were also studied by X-ray diffractometry, giving a thorough picture of the cyclization process. In preliminary tests of the effects of HL1 and [ZnL21(H2O)] on rat paw inflammatory edema induced by carrageenan, HL1 showed antiinflammatory activity.
• New lead(II) complexes with N,S-ligands, including a lead pyrazolonate with unusual packing flexibility
  作者：José S. Casas、Eduardo E. Castellano、Javier Ellena、María S. García-Tasende、Agustín Sánchez、José Sordo、Ángeles Touceda、Saulo Vázquez Rodríguez

  DOI：10.1016/j.poly.2007.05.016

  日期：2007.9

  The reaction of lead(II) acetate in methanol with thiosemicarbazones derived from beta-keto esters and beta-keto amides (HTSCs) afforded two lead(II) thiosernicarbazonates and numerous homoleptic ([PbL2]) and/or heteroleptic ([Pb(OAc)L]) complexes containing deprotonated pyrazolones L- formed by metal-induced cyclization of the starting HTSC ligands. All the complexes isolated were characterized by IR spectroscopy in the solid state and by H-1 and 13 C NMR spectroscopy in DMSO solution; in addition, crystals containing [Pb(L 6)21 and [Pb(L-7)(2)] were examined by X-ray crystallography. [Pb(L-6)(2)] center dot 0.5H(2)O center dot 0.3MeOH (HL6 = 4-ethyl-2,5-dihydro-3-methyl-5-oxo-1Hpyrazole- I-carbothiamide) showed three types of molecule with significant structural differences that appear to be determined by packing interactions. In all three molecules the Pb...Ph distances are very short [3.6096(8)-3.7562(8) angstrom], but den sity-functional-theoretic calculations at the B3LYP level do not support the existence of Pb-Pb bonds. In [Pb(L-7)(2)] (HL7 = N-ethyl-2,5-dihydro-3-methyl-5-oxo-1Hpyrazole-1-carbothiamide) all the molecules are of a single type, and they are linked in a three-dimensional network by weak intermolecular Ph...O bonds. (c) 2007 Elsevier Ltd. All rights reserved.