Perfluoro-1-(butylimino)butyl isothiocyanate | 857879-73-3

• 分子结构分类: 有机化合物
• 英文名称: Perfluoro-1-(butylimino)butyl isothiocyanate
• 英文别名: 2,2,3,3,4,4,4-heptafluoro-N-(1,1,2,2,3,3,4,4,4-nonafluorobutyl)butanimidoyl isothiocyanate
• CAS: 857879-73-3
• 化学式: C₉F₁₆N₂S
• 分子量: 472.153
• InChiKey: KVDCDQFLIWUIPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  56.8
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  Perfluoro-1-(butylimino)butyl isothiocyanate 、 3,3,3,-三氟-2-(三氟甲基)-1,2-氧化丙烯 以 四氢呋喃 为溶剂， 以46%的产率得到N-(5,5-bis(trifluoromethyl)-1,3-oxathiolan-2-ylidene)-2,2,3,3,4,4,4-heptafluoro-N'-(perfluorobutyl)butanimidamide
  参考文献：
  名称：

  Synthesis of trifluoromethylated heterocycles using partially fluorinated epoxides

  摘要：

  Reaction of 2-trifluoromethyl- (1) and 2,2-bis(trifluoromethyl)- (2) oxiranes with a variety of sulfur nucleophiles proceeds rapidly and under mild conditions. For example, epoxide 2 reacts with aqueous solution of Na(2)S, producing S[CH(2)C(CF(3))(2)OH](2). Reaction of 2 with Na(2)S(2)O(3) leads to the formation of the corresponding Bunte salt. Interaction of 2 with NaSCN in water proceeds exothermically and results in high-yield formation of cyclic imine 5. Although this material can be isolated, it has limited stability and undergoes cyclotrimerization at ambient temperature, giving the corresponding 1,3,5-triazine. A number of heterocyclic compounds containing pendant -CH(2)C(CF(3))(2)OH group were prepared by the reaction of the corresponding thio-derivatives, such as pyridine-2-thiole with epoxide 2. It was found that fluoride anion catalyzes the reaction of epoxides 1 and 2 with isothiocyanates carrying electron withdrawing groups at nitrogen. The reaction results in nucleophilic cyclization and formation of the corresponding exocyclic imines containing a 1,3-oxothiolane moiety. Carbon disulfide was also found to be active in this process, reacting with epoxides 1 and 2 at ambient to give the corresponding trifluoromethylated 1,3-oxathiolane-2-thiones in 58-65% yield. (c) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2010.11.003
• 作为产物：
  描述：

  potassium thioacyanate 、 全氟(5-氮杂-4-壬烯) 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 Perfluoro-1-(butylimino)butyl isothiocyanate
  参考文献：
  名称：

  Synthesis of trifluoromethylated heterocycles using partially fluorinated epoxides

  摘要：

  Reaction of 2-trifluoromethyl- (1) and 2,2-bis(trifluoromethyl)- (2) oxiranes with a variety of sulfur nucleophiles proceeds rapidly and under mild conditions. For example, epoxide 2 reacts with aqueous solution of Na(2)S, producing S[CH(2)C(CF(3))(2)OH](2). Reaction of 2 with Na(2)S(2)O(3) leads to the formation of the corresponding Bunte salt. Interaction of 2 with NaSCN in water proceeds exothermically and results in high-yield formation of cyclic imine 5. Although this material can be isolated, it has limited stability and undergoes cyclotrimerization at ambient temperature, giving the corresponding 1,3,5-triazine. A number of heterocyclic compounds containing pendant -CH(2)C(CF(3))(2)OH group were prepared by the reaction of the corresponding thio-derivatives, such as pyridine-2-thiole with epoxide 2. It was found that fluoride anion catalyzes the reaction of epoxides 1 and 2 with isothiocyanates carrying electron withdrawing groups at nitrogen. The reaction results in nucleophilic cyclization and formation of the corresponding exocyclic imines containing a 1,3-oxothiolane moiety. Carbon disulfide was also found to be active in this process, reacting with epoxides 1 and 2 at ambient to give the corresponding trifluoromethylated 1,3-oxathiolane-2-thiones in 58-65% yield. (c) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2010.11.003