N-(ethoxycarbonyl)ferrocenecarbothioamide | 867197-86-2

• 英文名称: N-(ethoxycarbonyl)ferrocenecarbothioamide
• 英文别名: ferrocenyl thioamide
• CAS: 867197-86-2
• 化学式: C₁₄H₁₅FeNO₂S
• 分子量: 317.192
• InChiKey: RVTJYAHYXXIHCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  二茂铁 、 异硫氰酰甲酸乙酯 在 甲烷磺酸 作用下， 以48%的产率得到N-(ethoxycarbonyl)ferrocenecarbothioamide
  参考文献：
  名称：

  Ferrocenyl and pyrenyl thioimidates bearing terminal acetylenic groups. Synthesis and “click” reaction with 3'-azido-3'-deoxythymidine affording novel redox-active and fluorescent thymidine conjugates

  摘要：

  Thioamides Ar(C=S) NHCOOEt (Ar = ferrocenyl and 1-pyrenyl) obtained from ferrocene and pyrene and ethoxycarbonyl isothiocyanate react under Mitsunobu conditions with propargyl and homopropargyl alcohols, yielding the corresponding N-(ethoxycarbonyl)thioimidates containing a terminal acetylene functionality. These compounds undergo Cu(I)-catalyzed "click reaction" with 3'-azido-3'-deoxythymidine (AZT) affording novel redox-active ferrocenyl and fluorescent, environmentally sensitive pyrenyl thymidine conjugates.

  DOI：

  10.3998/ark.5550190.0013.636

文献信息

• Reaction of ferrocenecarbothioamide and N-(ethoxycarbonyl)ferrocenecarbothioamide with alkyl halides
  作者：Anna Wrona、Marcin Palusiak、Janusz Zakrzewski

  DOI：10.1016/j.jorganchem.2007.10.049

  日期：2008.1

  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.