trifluoromethylthioferrocene | 1189176-83-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: trifluoromethylthioferrocene
• 英文别名: Cyclopenta-1,3-diene;iron(2+);1-(trifluoromethylsulfanyl)cyclopenta-1,3-diene；cyclopenta-1,3-diene;iron(2+);2-(trifluoromethylsulfanyl)cyclopenta-1,3-diene
• CAS: 1189176-83-7
• 化学式: C₁₁H₉F₃FeS
• 分子量: 286.101
• InChiKey: CLDWBPOKEXHMSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-(三氟甲硫基)邻苯二甲酰亚胺 、 ferrocene boronic acid 在 2,2'-联吡啶 、 potassium carbonate 、 copper(l) chloride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 18.0h， 以54%的产率得到trifluoromethylthioferrocene
  参考文献：
  名称：

  亲电子稳定的N-（三氟甲硫基）邻苯二甲酰亚胺对硼酸和炔烃的直接催化三氟甲硫基化

  摘要：

  已开发出一种新的安全的合成N-（三氟甲基硫代）邻苯二甲酰亚胺的方法，N-（三氟甲基硫代）邻苯二甲酰亚胺是一种方便且稳定的直接三氟甲基硫代化试剂。N-（三氟甲硫基）邻苯二甲酰亚胺可用作F 3 CS +的亲电子源，并在铜催化下易于与硼酸和炔烃反应。含有CF 3 S的分子作为生物活性剂的实用性，所采用的反应条件温和以及对官能团的高度耐受性证明了这种新方法在有机合成以及工业制药和农用化学研究以及发展。

  DOI：

  10.1002/anie.201307484

文献信息

• [EN] ORGANOMETALLIC COMPOUNDS FOR USE AS ANTHELMINTICS<br/>[FR] COMPOSÉS ORGANOMÉTALLIQUES À UTILISER COMME ANTHELMINTIQUES
  申请人：UNIV ZUERICH

  公开号：WO2015044397A1

  公开（公告）日：2015-04-02

  The invention comprises a compound characterized by a general formula (1), wherein OM is an organometallic compound independently selected from the group of an unsubstituted or substituted metal sandwich compound, an unsubstituted or substituted half metal sandwich compound or a metal carbonyl compound, and wherein at least one of RL and RR is selected from formula (A), formula (B), formula (C), or formula (D) and their use for in a method of treatment of disease, in particular their use against helminths.

  该发明包括一种化合物，其具有一般式（1），其中OM是独立选择自未取代或取代的金属夹心化合物、未取代或取代的半金属夹心化合物或金属羰基化合物的有机金属化合物，并且RL和RR中至少有一个选择自式（A）、式（B）、式（C）或式（D），以及它们用于治疗疾病的方法，特别是它们用于对抗蠕虫。
• Novel, Mercury-Free Synthetic Pathway for Trifluoromethylthio-Substituted Metallocenes
  作者：Jeannine Hess、Sandro Konatschnig、Sandra Morard、Vanessa Pierroz、Stefano Ferrari、Bernhard Spingler、Gilles Gasser

  DOI：10.1021/ic403169z

  日期：2014.4.7

  A novel synthetic pathway for trifluoromethylthioferrocene (3), which does not involve the use of toxic mercury(II)-based reagents, is described. The novel approach involves first the treatment of the commercially available bromoferrocene (la) with NaSCN in the presence of copper(+I) to yield thiocyanatoferrocene (1), and then the reaction of 1 with the Rupper-Prakash reagent and tetrabutylammonium fluoride (TBAF) to give 3 in an overall yield of 60%. This approach could be extended for the preparation of thiocyanato-(4) and trifluoromethylthio-ruthenocene (7), which are herein both reported for the first time. Interestingly, diferrocenyl disulfide (2a) and diruthenocenyl disulfide (5) could be isolated as side-products during the synthesis of 3 and 7, respectively. All new compounds were unambiguously characterized by H-1, C-13, and F-19 NMR spectroscopy, mass spectrometry, cyclic voltammetry, elemental analysis, as well by X-ray crystallography for 1, 4, 4b, 5, 6, and 7.1-7 were further tested for their toxic activity on cervical cancer (HeLa) and noncancerous (MRC-5) cell lines. All organometallic compounds were found either to be nontoxic or to have a moderate toxicity toward the cell lines used in this study.