Perfluoro(3-isothiocyanato-2-methyl-2-pentene) | 133586-43-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 异硫氰酸盐
• 英文名称: Perfluoro(3-isothiocyanato-2-methyl-2-pentene)
• 英文别名: perfluoro-2-methylpent-2-en-3-yl isothiocyanate；1,1,1,4,4,5,5,5-Octafluoro-3-isothiocyanato-2-(trifluoromethyl)pent-2-ene
• CAS: 133586-43-3
• 化学式: C₇F₁₁NS
• 分子量: 339.132
• InChiKey: BMOYCSJTFCYLFM-UHFFFAOYSA-N

物化性质

• 沸点：
  119-120°C

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  44.4
• 氢给体数：
  0
• 氢受体数：
  13

安全信息

• 安全说明：
  S23
• 危险类别码：
  R23/24/25
• 海关编码：
  2930909090
• 危险品运输编号：
  UN 2810

反应信息

• 作为反应物：
  描述：

  Perfluoro(3-isothiocyanato-2-methyl-2-pentene) 在 氯 、 铁粉 作用下， 反应 4.0h， 以72%的产率得到perfluoro-1-ethyl-2-methyl-1-propenyliminochloromethanesulfenyl chloride
  参考文献：
  名称：

  硫杂环丁烷在杂环的合成中。3.全氟-1-乙基-2-甲基-1-丙烯基-亚氨基氯甲烷亚磺酰氯与1-烯丙基-2-甲氧基苯的相互作用

  摘要：

  DOI：

  10.1007/s10593-006-0247-3
• 作为产物：
  描述：

  全氟(2-甲基-2-戊烯) 、 sodium thiocyanide 以 乙腈 为溶剂， 反应 3.0h， 以80%的产率得到Perfluoro(3-isothiocyanato-2-methyl-2-pentene)
  参考文献：
  名称：

  Furin, G. G., Russian Journal of Organic Chemistry, 1995, vol. 31, # 4, p. 465 - 468

  摘要：

  DOI：

文献信息

• Synthesis of Heterocyclic Compounds Containing Perfluoroalkyl Groups. Reactions of Perfluoro(2-methyl-2-pentene) and Perfluoro(5-aza-4-nonene) with N,S-Dinucleophiles
  作者：G. G. Furin、E. L. Zhuzhgov

  DOI：10.1007/s11178-005-0183-1

  日期：2005.3

  Perfluoro(2-methyl-2-pentene) and perfluoro(5-aza-4-nonene) react with 1,4,5,6-tetrahydropyrimi-dine-2-thiol, pyridine-2-thiol, and 1,2,4-triazole-3-thiol to afford fused heterocyclic systems, while their reactions with tetrahydrothiazole-2-thione and pyrimidine-2-thiol result in replacement of the fluorine atom at the double bond. Treatment of 3,3,3-trifluoro-1-pentafluoroethyl-2-trifluoromethyl-1-pentenyl isothiocyanate with ammonia gives N-(3,3,3-trifluoro-1-pentafluoroethyl-2-trifluoromethyl-1-propenyl)thiourea which undergoes ring closure to 4-tetrafluoroethylidene-5,5-bis(trifluoromethyl)-4,5-dihydrothiazol-2-amine. Possible cyclization paths and the effect of the 1,3(N,S)-dinucleophile nature on the direction of nucleophilic addition at the double bond are discussed.

  全氟(2-甲基-2-戊烯)和全氟(5-氮-4-壬烯)与1,4,5,6-四氢嘧啶-2-硫醇、吡啶-2-硫醇和1,2,4-三唑-3-硫醇反应，生成融合的杂环系统，而它们与四氢噻唑-2-硫酮和嘧啶-2-硫醇的反应则导致双键处氟原子的取代。将3,3,3-三氟-1-五氟乙基-2-三氟甲基-1-烯基异硫氰酸酯与氨反应可得到N-(3,3,3-三氟-1-五氟乙基-2-三氟甲基-1-丙烯基)硫脲，该化合物经过环化形成4-四氟乙烯基-5,5-双(三氟甲基)-4,5-二氢噻唑-2-胺。讨论了可能的环化路径及1,3(N,S)-二亲核试剂的性质对双键处亲核加成方向的影响。
• Reaction of perfluoro-2-methylpent-2-en-3-yl isothiocyanate with methylamine
  作者：G. G. Furin、I. Yu. Bagryanskaya、Yu. V. Gatilov

  DOI：10.1007/bf02495931

  日期：1997.7

  Abstract3-Methyl-2-methylamino-6-pentafluoroethyl-5-trifluoromethyl-3H-pyrimidine-4-thione was synthesized by treatment of perfluoro-2-methylpent-2-en-3-yl isothiocyanate with methylamine. The molecular structure of this pyrimidine-4-thione was studied by X-ray diffraction analysis.

  摘要 3-甲基-2-甲基氨基-6-五氟乙基-5-三氟甲基-3H-嘧啶-4-硫酮采用甲胺处理全氟-2-甲基戊-2-烯-3-基异硫氰酸酯合成。通过 X 射线衍射分析研究了这种嘧啶-4-硫酮的分子结构。
• Perfluoro-2-methyl-2-penten-3-yl isothiocyanate, a versatile perfluorinated building block Reactions with amines and enamines
  作者：Vera Ya. Popkova、Klaus Burger、Eberhardt Herdtweck

  DOI：10.1016/0022-1139(95)03322-7

  日期：1995.12

  A preparatively simple access to polyfluorinated 1-thia-3-aza-1,3-dienes, 4,5-dihydro-1,3-thiazoles and 6H-1,3-thiazines from the reaction of perfluoro-2-methyl-2-penten-3-yl isothiocyanate with amines and enamines is described.

  通过全氟-2-甲基-三氟甲烷的反应，可轻松制备多氟化的1-硫杂-3-氮杂-1,3-二烯，4,5-二氢-1,3-噻唑和6 H -1,3-噻嗪描述了具有胺和烯胺的2-戊烯基-3-异硫氰酸异氰酸酯。
• Reaction of perfluoro-2-methylpent-2-en-3-yl isothiocyanate with ethyl and isopropyl alcohols
  作者：G. G. Furin、I. Yu. Bagryanskaya、Yu. V. Gatilov、E. L. Zhuzhgov

  DOI：10.1007/bf02494507

  日期：1998.10

  Perfluoro-2-methylpent-2-en-3-yl isothiocyanate reacts with ethyl or isopropyl alcohols in the presence of NEt3 to give derivatives of 4,5-dihydrothiazole and ethoxy(ethylthio)methylene-(1,1,1,4,4,5,5,5-octafluoro-2-trifluoromethylpent-2-en-3-yl)amine and isopropoxy(isopropylthio)methylene-(1,1,1,4,4,5,5,5-octafluoro-2-trifluoromethylpent-2-en-3-yl)amine, respectively. Heating of ethyl or isopropy

  全氟-2-甲基戊-2-烯-3-基异硫氰酸酯在 NEt3 存在下与乙醇或异丙醇反应生成 4,5-二氢噻唑和乙氧基（乙硫基）亚甲基-(1,1,1,4, 4,5,5,5-octafluoro-2-trifluoromethylpent-2-en-3-yl)amine and isopropoxy(isopropylthio)methylene-(1,1,1,4,4,5,5,5-octafluoro-2) -三氟甲基戊-2-烯-3-基)胺，分别。乙基或异丙基 N-（全氟-2-甲基-2H-戊基-3-氨基）硫代氨基甲酸酯与碳酸钾在 DMF 中加热产生相同的产物加上 3-四氟亚乙基-5,5-双（三氟甲基）噻唑烷-2-酮。后者的结构由X射线衍射分析证实。该化合物在溶液 (CCl4) 和固态 (KBr) 中的红外光谱数据表明分子间 NH 的形成...
• Synthesis of trifluoromethylated heterocycles using partially fluorinated epoxides
  作者：Viacheslav A. Petrov、Will Marshall

  DOI：10.1016/j.jfluchem.2010.11.003

  日期：2011.1

  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.