trifluorothioacetyl chloride | 2375-37-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 硫代碳卤化物
• 英文名称: trifluorothioacetyl chloride
• 英文别名: Trifluoroethanethioyl chloride；2,2,2-trifluoroethanethioyl chloride
• CAS: 2375-37-3
• 化学式: C₂ClF₃S
• 分子量: 148.536
• InChiKey: QHIKKQMUMQOCPQ-UHFFFAOYSA-N

物化性质

• 沸点：
  28-29 °C
• 密度：
  1.574±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  32.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trifluorothioacetyl chloride 生成 2,4-bis(trifluoromethyl)-2,4-dichloro-1,3-dithiethane
  参考文献：
  名称：

  Middleton, W. J.; Howard, E. G.; Sharkey, W. H., Journal of the American Chemical Society, 1961, vol. 83, p. 2590

  摘要：

  DOI：
• 作为产物：
  描述：

  Bis-(1.1-dichlor-2.2.2-trifluoraethyl)-quecksilber 在 sulfur 作用下， 生成 trifluorothioacetyl chloride
  参考文献：
  名称：

  Fluorothiocarbonyl Compounds.¹ I. Preparation of Thio Ketones, Thioacyl Halides, and Thio Esters

  摘要：

  DOI：

  10.1021/jo01016a008

文献信息

• Perfluorothioalkanoyl halides. Preparation from sulfides
  作者：Thoai Nguyen、Claude Wakselman

  DOI：10.1016/s0022-1139(00)81999-5

  日期：1987.4

  Perfluorothioalkanoyl halides were generated from alkyl perfluoroalkyl sulfides by reaction with TiF4, TiCl4 or ClS03H. The alkyl groups were benzyl or methyl, the former was more suitable. An α-bromoperfluoroalkyl-sulfide gave a perfluorothioalkanoyl halide more easily than the corresponding α-chloro sulfide which gave the thioalkanoyl chloride. An exchange between the α-halogen atom X of the sulfide

  通过与TiF 4，TiCl 4或ClSO 3 H反应，由烷基全氟烷基硫化物生成全氟硫代烷酰卤。烷基为苄基或甲基，前者更合适。与产生硫代链烷酰氯的相应α-氯硫化物相比，α-溴全氟烷基硫化物更容易得到全氟硫代链烷酰卤。硫化物R F CFXSR H（X = Cl，Br）的α卤素原子X与路易斯酸的卤素原子之间可能发生交换。
• Synthesis and reactivity of fluorine-containing thiols and thioacyl halides
  作者：A. Yu. Sizov、A. N. Kovregin、R. N. Serdyuk、M. V. Vorob’ev、V. A. Porosyatnikov、A. A. Tsvetkov、D. O. Korneev、A. F. Ermolov

  DOI：10.1007/s11172-006-0399-4

  日期：2006.7

  α-hydropolyfluoroalkanethiols and polyfluorothioacyl halides via thermal splitting of benzyl polyfluoroalkyl sulfides under the action of phosphorus pentoxide was proposed. The thiols obtained were used as starting materials for the synthesis of α-hydropolyfluoroalkanesulfenyl chlorides. The properties of the resulting F,S-containing compounds were studied.

  提出了在五氧化二磷作用下通过苄基多氟烷基硫化物的热裂解制备α-氢多氟烷硫醇和多氟硫酰卤的路线。获得的硫醇用作合成α-氢多氟烷亚磺酰氯的原料。研究了所得含 F,S 化合物的性质。
• 2-Polyfluoroalkyl thiopyrylium salts: synthesis and reactions with nucleophiles
  作者：Sergiy A. Siry、Vadim M. Timoshenko

  DOI：10.1016/j.tetlet.2010.09.131

  日期：2010.12

  2-Polyfluoroalkylthiopyrylium salts have been synthesized by oxidative aromatization of 2-polyfluoroalkyl-2H-thiopyrans with triphenylmethane tetrafluoroborate. Nucleophilic addition of methanol, sodium azide, or urea to 2-trifluoromethylthiopyrylium tetrafluoroborate in a basic medium proceeds at the α-position to give the corresponding 2-substituted 6-trifluoromethyl-2H-thiopyrans whereas imidazoles

  已经通过用三苯基甲烷四氟硼酸酯对2-聚氟烷基-2 H-硫代吡喃进行氧化芳构化来合成2-多氟烷基硫代吡啶鎓盐。亲核加成甲醇中，在α位的碱性介质进行叠氮化钠，或尿素到2- trifluoromethylthiopyrylium四氟硼酸盐，得到相应的2-取代的6-三氟甲基-2- ħ -thiopyrans而咪唑，1,2-含氟， 3-三唑，硫羟乙酸钾和硝基甲烷钠提供2 H-和4 H-硫代吡喃的混合物。6-三氟甲基-2-甲氧基-2 H-噻喃的顺式-二羟基化反应可得到含氟的硫庚基吡喃糖苷衍生物8。
• The synthesis and properties of 6-trifluoromethyl-substituted thiopyrano[3,4-d]isoxazole derivatives
  作者：Serhii A. Siryi、Vadim M. Timoshenko、Yurii G. Vlasenko、Eduard B. Rusanov、Yuriy G. Shermolovich

  DOI：10.1007/s10593-015-1750-1

  日期：2015.7

  cleavage of the isoxazoline ring of the obtained compounds led to the formation of 6-trifluoromethyl-2Н-thiopyran derivatives with nitrile or carbonyl-containing functionality at position 3. Transformations of the thiopyran moiety in 4,7а-dihydro-3аН-thiopyrano[3,4-d]isoxazole were studied for the case of Pummerer reaction product with oxidized sulfur atom, ethyl 6-trifluoromethyl-4,7а-dihydro-3аН-thiopyrano[3

  小说的第一代表4,7а二氢3А Н -thiopyrano [3,4 -d ]异恶唑的杂环系统，作为含有酯基，羧基，或羟甲基在3位和6位三氟甲基是由获得的3 + 2]乙基cyanocarboxylate的环加成反应ñ氧化物和6-三氟甲基-2- Н噻喃，随后的进一步转化的乙基-6-三氟甲基4,7а二氢3А Н -thiopyrano [3,4 -d ]异恶唑-3-羧酸酯中间体。所得化合物的异恶唑啉环的断裂导致6-三氟甲基-2Н的形成与腈或含羰基的官能度-噻喃衍生物在位置在噻喃部分的3变换4,7а二氢3А Н -thiopyrano [3,4 -d ]异恶唑进行了研究用于Pummerer重反应产物的情况下与氧化的硫原子，乙基-6-三氟甲基4,7а二氢3А Н -thiopyrano [3,4 -d ]异恶唑-3-羧酸甲酯5-氧化物，将其转化为乙基-6-三氟甲基-4 Н -thiopyrano [3
• Pummerer Reactions of Thiopyran Derivatives as a Method for the Preparation of Trifluoro-Methyl-Substituted Thiolanes with Antiviral Activity
  作者：S. A. Siry、V. M. Timoshenko、Yu. G. Vlasenko、G. V. Baranova、S. D. Zagorodnya、N. V. Nesterova

  DOI：10.1007/s10593-014-1497-0

  日期：2014.7

  6-dihydro-2Н-thiopyran 1-oxides undergo a vinylogous Pummerer reaction upon interaction with trifluoroacetic anhydride, forming 2-(p-tolylsulfanyl)-4-tri-fluoroacetoxy-2-trifluoromethyl-3,4-dihydro-2Н-thiopyrans. The hydrolysis, acetylation, and free radical desulfanylation of these compounds with a subsequent oxidation of the sulfur atom leads to 4-acetoxy-2-trifluoromethyl-3,4-dihydro-2Н-thiopyran 1-oxides. The Pummerer

  2-（对甲苯硫基）-2-三氟甲基-3,6-二氢-2Н-硫代吡喃1-氧化物与三氟乙酸酐相互作用后发生乙烯基Pummerer反应，形成2-（对甲苯硫基）-4-三氟乙酰氧基- 2-三氟甲基-3,4-二氢-2Н-噻喃。这些化合物的水解，乙酰化和自由基脱硫基作用以及随后的硫原子的氧化导致生成4-乙酰氧基-2-三氟甲基-3,4-二氢-2？-噻喃-1-氧化物。后者与乙酸酐和三氟化硼醚化物的Pummerer加成反应会导致环收缩并形成3-乙酰氧基-2-二乙酰氧基甲基-5-（三氟甲基）硫杂环戊烷，可以用硼氢化钠将其转化为3具有抗病毒活性的-羟基-2-羟甲基-5-（三氟甲基）硫杂环戊烷。