Acetessigsaeure-o-anisidid-thiosemicarbazon | 329070-55-5

• 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: Acetessigsaeure-o-anisidid-thiosemicarbazon
• 英文别名: o-acetoacetanisidide thiosemicarbazone；3-(carbamothioylhydrazinylidene)-N-(2-methoxyphenyl)butanamide
• CAS: 329070-55-5
• 化学式: C₁₂H₁₆N₄O₂S
• 分子量: 280.351
• InChiKey: OYSAWVVYYFTVDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Acetessigsaeure-o-anisidid-thiosemicarbazon 以 甲醇 、 二甲基亚砜 为溶剂， 生成 (Zn(0-acetoacetanisidide thiosemicarbazonate)2)*DMSO
  参考文献：
  名称：

  Metal-Induced Cyclization of Thiosemicarbazones Derived from β-Keto Amides and β-Keto Esters:  Open-Chain and Cyclized Ligands in Zinc(II) Complexes

  摘要：

  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.

  DOI：

  10.1021/ic0111942
• 作为产物：
  描述：

  邻甲氧基-N-乙酰乙酰苯胺 、 氨基硫脲 以 甲醇 为溶剂， 反应 1.0h， 以80%的产率得到Acetessigsaeure-o-anisidid-thiosemicarbazon
  参考文献：
  名称：

  Syamal, A.; Ahmed, S.; Niazi, M. A. Bari, Journal of the Indian Chemical Society, 1983, vol. 60, p. 493 - 495

  摘要：

  DOI：

文献信息

• Diphenyllead(IV) thiosemicarbazonates and pyrazolonates: Synthesis and characterization
  作者：José S. Casas、Eduardo E. Castellano、Javier Ellena、María S. García-Tasende、Agustín Sánchez、José Sordo、Ángeles Touceda

  DOI：10.1016/j.poly.2009.01.004

  日期：2009.4

  Cyclization of thiosemicarbazones derived from beta-keto esters and beta-keto amides (HTSC) in the presence of diphenyllead(IV) acetate was explored in methanol solution at room temperature and under reflux. All beta-keto ester TSCs underwent cyclization to give the corresponding pyrazolone (HL), which, except in one case, deprotonated and coordinated the PbPh22+ moiety to form homoleptic [PbPh2(L)(2)] or heteroleptic [PbPh2(OAc)(L)] derivatives. Cyclization did not occur with beta-keto amide TSCs and only [Pbph(2)(TSC)(2)] or [PbPh2(OAc)(TSC)] thiosernicarbazonates were isolated. The complexes were characterized by IR spectroscopy in the solid state and by H-1, C-13 and Pb-207 NMR spectroscopy in DMSO-d(G) solution, in which they evolve and decompose with time. Additionally, crystals of p-acetoacetanisidide thiosemicarbazone (HTSC10), [PbPh2(OAc)(L-5)] center dot MeOH (HL5 = 2,5-dihydro-3,4-dimethyl-5-oxo-1H-pyrazolone-1-carbothioamide), [PbPh2Cl(L-2)] (HL2 = 2,5-dihydro-5-oxo-3-phenyl-1H-pyrazolone-1-carbothioamide), [PbPh2(OAc)(TSC8)]center dot 2MeOH (HTSC8 = acetoacetanilide thiosemicarbazone), [PbPh2(OAc)(TSC10)]center dot H2O and [PbPh2(OAc)(TSC11)] center dot 0.75MeOH (HTSO11 = o-acetoacetotoluidide) were studied by X-ray crystallography. The complexes, monomers or dimers with almost linear C-Pb-C moieties, are compared with the corresponding derivatives of Pb(II). (C) 2009 Elsevier Ltd. All rights reserved.
• 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.
• Syamal, A.; Ahmad, S.; Gupta, B. K., Revue de Chimie Minerale, <hi>1983</hi>, vol. 20, p. 181 - 185
  作者：Syamal, A.、Ahmad, S.、Gupta, B. K.

  DOI：——

  日期：——
• Syamal, A.; Ahmed, S.; Niazi, M. A. Bari, Journal of the Indian Chemical Society, 1983, vol. 60, p. 493 - 495
  作者：Syamal, A.、Ahmed, S.、Niazi, M. A. Bari

  DOI：——

  日期：——
• 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.