ferrocenecarbothioamide | 582296-40-0

• 英文名称: ferrocenecarbothioamide
• CAS: 582296-40-0
• 化学式: C₁₁H₁₁FeNS
• 分子量: 245.128
• InChiKey: KBUKCJJXWUFICW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  ferrocenecarbothioamide 在 K₂CO₃ 、 p-NO₂C₆H₄CH₂Br or C₆H₅CH₂Cl or p-CNC₆H₄CH₂Br 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以96%的产率得到1-cyanoferrocene
  参考文献：
  名称：

  Reaction of ferrocenecarbothioamide and N-(ethoxycarbonyl)ferrocenecarbothioamide with alkyl halides

  摘要：

  Reaction of ferrocenecarbothioamide and N-(ethoxycarbonyl)ferrocenecarbothioamide with alkyl (mainly benzyl) halides in the presence of K2CO3 has been studied. The former compound yielded cyanoferrocene in high yield whereas the latter was transformed into the corresponding thioimidates as a result of S-alkylation and deprotonation. The molecular structure of S-p-nitrobenzyl-N-(ethoxycarbonyl)-ferrocenethioimidate was determined by single-crystal X-ray analysis and revealed the E configuration. The plausible reaction mechanism is discussed. (C) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2007.10.049
• 作为产物：
  描述：

  N-(ethoxycarbonyl)ferrocenecarbothioamide 在 AlCl₃ 作用下， 以 苯 为溶剂， 以70%的产率得到ferrocenecarbothioamide
  参考文献：
  名称：

  Ferrocenecarbothioamide and N-ethoxycarbonylferrocenecarbothioamide: Synthesis, structure and application in synthesis of 2,4-diferrocenylthiazole

  摘要：

  Ferrocenecarbothioamide (1) and its N-ethoxycarbonyl derivative (2) were synthesised by a Friedel-Crafts type reaction of ferrocene with potassium thiocyanate and ethoxycarbonyl isothiocyanate, respectively, in a strongly acidic medium. The X-ray structure of I was determined and shows conjugation between the ferrocene moiety and the thioamido group. Compound I reacts with chloroacetylferrocene affording 2,4-diferrocenylthiazole, whose structure was determined by X-ray diffraction and electronic properties studied by cyclic voltammetry. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.06.037

文献信息

• Design, Synthesis and Biological Evaluation of Ferrocenyl Thiazole and Thiazolo[5,4-<i>d</i>]thiazole Catechols as Inhibitors of 5-hLOX and as Antibacterials against <i>Staphylococcus aureus</i>. Structural Relationship and Computational Studies
  作者：Erick Flores、Michelle Muñoz-Osses、Claudia Torrent、Yesseny Vásquez-Martínez、Alejandra Gómez、Marcelo Cortez-San Martin、Andrés Vega、Angel A. Martí、Fernando Godoy、Carolina Mascayano

  DOI：10.1021/acs.organomet.0c00284

  日期：2020.7.27

  fragment is oriented to the active iron(III) site present in 5-hLOX; kinetics and FRAP assays together with electrochemical analysis suggest a redox mechanism mediated by water (Fe(III) from enzyme/Fe(II) from complex) accompanied by the blocking of the substrate approach, being consistent with competitive inhibition. The ferrocenyl, together with the thiazole and catechol fragments, drastically improves

  在寻找可用于治疗多种炎症相关疾病的新型人5-脂氧合酶（5-hLOX）抑制剂时，衍生了3种新的由2,4-噻唑和噻唑[5,4- d ]噻唑（（η 5 -C 5 H ^ 4 -2,4-噻唑3,4-二羟基苯基）铁（η 5 -C 5 H ^ 5）（3），（η 5 -C 5 H ^ 4 -2,4 -噻唑基-苯基）的Fe（η 5 -C 5 H ^ 5）（4），和（η 5 -C 5 H ^ 4 -噻唑并[5,4- d]噻唑-3,4-二羟基苯）的Fe（η 5 -C 5 H ^ 5）（5））的合成和评价。二茂铁基，噻唑和邻苯二酚片段之间的协同作用已得到证实，并在评估二茂铁基（1）和邻苯二酚（2）前体以及有机衍生物6的活性方面得到了证实，类似于NDGA结构。噻唑衍生物3是最好的5-hLOX抑制剂（抑制率为85.8％，5-hLOX的IC 50 = 0.9±0.7μM，人细胞中为22±1.1μM），其次是复合物4（抑制率为74
• An expedient approach to ferrocenyl thioamides via Fischer carbenes
  作者：César Sandoval-Chávez、José G. López-Cortés、Alejandro I. Gutiérrez-Hernández、María C. Ortega-Alfaro、Alfredo Toscano、Cecilio Alvarez-Toledano

  DOI：10.1016/j.jorganchem.2009.07.044

  日期：2009.11

  Oxidative demetalation of Fischer ferrocenyl ethoxy carbene complexes (1a–c, M = Cr, Mo, W) and new Fischer ferrocenyl R-amino carbene complexes [2–5 (a–c), 11–15 (a–c), and 21–22 (a–c); M = Cr, Mo, W; R = H, CH3, C2H5, C3H7, (CH2)2OH, (CH2)3OH, (CH2)2(OMe)2, (CH2)3N(Me)2, CH2CHCH2, (CH2)2OSi(CH3)3, (CH2)3OSi(CH3)3] with elemental sulfur–NaBH4 were carried out under mild conditions, obtaining O-ethyl

  Fischer二茂铁基乙氧基卡宾配合物（1a – c，M = Cr，Mo，W）和新的Fischer二茂铁基R-氨基卡宾配合物[ 2 – 5（a – c），11 – 15（a – c）和21 – 22（a – c）；M = Cr，Mo，W；R = H，CH 3，C 2 H 5，C 3 H 7，（CH 2）2 OH，（CH 2）3 OH，（CH2）2（OMe）2，（CH 2）3 N（Me）2，CH 2 CH CH 2，（CH 2）2 OSi（CH 3）3，（CH 2）3 OSi（CH 3）3 ]元素硫–NaBH 4在温和的条件下进行，获得了O-乙基二茂铁硫代碳酸盐（6）和新型二茂铁硫代酰胺（7 – 10和16 – 20））的良率。