[4,5-dimethyl-2-(1,1,2,2,3,3,4,4-octafluorobutyl)-3,6-dihydro-2H-thiopyran-2-yl]-(p-tolyl)amine | 1214893-13-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [4,5-dimethyl-2-(1,1,2,2,3,3,4,4-octafluorobutyl)-3,6-dihydro-2H-thiopyran-2-yl]-(p-tolyl)amine
• 英文别名: 3,4-dimethyl-N-(4-methylphenyl)-6-(1,1,2,2,3,3,4,4-octafluorobutyl)-2,5-dihydrothiopyran-6-amine
• CAS: 1214893-13-6
• 化学式: C₁₈H₁₉F₈NS
• 分子量: 433.409
• InChiKey: ASKPFRHMIPYBOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [4,5-dimethyl-2-(1,1,2,2,3,3,4,4-octafluorobutyl)-3,6-dihydro-2H-thiopyran-2-yl]-(p-tolyl)amine 在 三氟甲磺酸 作用下， 以 正己烷 为溶剂， 以30%的产率得到3,4-dimethyl-6-(1,1,2,2,3,3,4,4-octafluorobutyl)-2H-thiopyran
  参考文献：
  名称：

  First synthesis of 2-aminosubstituted-2-perfluoroalkyl-3,6-dihydro-2H-thiopyrans by hetero-Diels–Alder reactions of fluorinated thioamides under microwave heating

  摘要：

  This Letter presents the first examples of hetero-Diels-Alder reactions of polyfluoroalkanethiocarboxylic acid amides and 2,3-dimethylbutadiene under microwave heating. Cycloaddition reactions proved to be dependent on the nature of perfluoroalkyl chain and on the substituents attached to the nitrogen atom. Formation of ammonium salts was also performed by simple treatment of the corresponding cycloadducts with trifluoromethanesulfonic acid. In the case of octafluorobutyl-substituted derivative, one spontaneous desamination reaction took place leading to new 2H-thiopyran. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.064
• 作为产物：
  描述：

  N-(4-methylphenyl)-2,2,3,3,4,4,5,5-octafluoropentanethioamide 、 2,3-二甲基-1,3-丁二烯 在 Weflon 作用下， 以 N-甲基吡咯烷酮 为溶剂， 以15%的产率得到[4,5-dimethyl-2-(1,1,2,2,3,3,4,4-octafluorobutyl)-3,6-dihydro-2H-thiopyran-2-yl]-(p-tolyl)amine
  参考文献：
  名称：

  First synthesis of 2-aminosubstituted-2-perfluoroalkyl-3,6-dihydro-2H-thiopyrans by hetero-Diels–Alder reactions of fluorinated thioamides under microwave heating

  摘要：

  This Letter presents the first examples of hetero-Diels-Alder reactions of polyfluoroalkanethiocarboxylic acid amides and 2,3-dimethylbutadiene under microwave heating. Cycloaddition reactions proved to be dependent on the nature of perfluoroalkyl chain and on the substituents attached to the nitrogen atom. Formation of ammonium salts was also performed by simple treatment of the corresponding cycloadducts with trifluoromethanesulfonic acid. In the case of octafluorobutyl-substituted derivative, one spontaneous desamination reaction took place leading to new 2H-thiopyran. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.064

文献信息

• Hetero-Diels–Alder reactions of perfluoroalkyl thioamides with electron-rich 1,3-dienes: synthesis of new 2-aminosubstituted-3,6-dihydro-2H-thiopyrans and related compounds
  作者：Oleksandr S. Kanishchev、Morgane Sanselme、Jean-Philippe Bouillon

  DOI：10.1016/j.tet.2012.11.086

  日期：2013.1

  Hetero-Diels–Alder reactions of perfluoroalkyl thioamides with electron-rich 1,3-dienes such as 2,3-dimethylbutadiene, isoprene or penta-1,3-diene gave a simple and efficient access to new 2-aminosubstituted-3,6-dihydro-2H-thiopyrans. Three different procedures were used depending on the nature of the polyfluoroalkyl chains (RF=CF3, (CF2)nCF3, (CF2)4H) and on the nitrogen substituents of the thioamides

  全氟烷基硫酰胺与富电子的1,3-二烯（例如2,3-二甲基丁二烯，异戊二烯或五，1,3-二烯）的杂狄尔斯-阿尔德反应使新的2-氨基取代的3,6的反应简单有效。 -二氢-2 H-硫代吡喃。根据多氟烷基链的性质（R F = CF 3，（CF 2）n CF 3，（CF 2）4 H）和硫代酰胺的氮取代基（R 1，R 2 = H，对-Tol，吗啉代，Ac）。此外，甲硅烷氧基二烯（1-或2-三甲基甲硅烷氧基-1,3-丁二烯和丹尼舍夫斯基二烯）与N-酰基，N-甲苯基三氟甲基硫代酰胺几乎在所有情况下均提供相应的3，6-二氢-2 H-噻喃或3-氧代-四氢噻喃。对于非对称的1,3-二烯，研究了反应的区域和立体化学（尤其是使用X射线衍射分析），表明与报道的氟代硫代羧基衍生物具有高度相似性。最后，两个甲硅烷基化的3,6-dihydro-2 H -thiopyrans经历了意外的碱基诱导的环收缩，得到了新的1,3-噻唑烷酮-4-酮。