3-Trifluoromethanesulfonylsulfanyl-propionic acid ethyl ester | 182677-48-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: 3-Trifluoromethanesulfonylsulfanyl-propionic acid ethyl ester
• 英文别名: Ethyl 3-(trifluoromethylsulfonylsulfanyl)propanoate
• CAS: 182677-48-1
• 化学式: C₆H₉F₃O₄S₂
• 分子量: 266.262
• InChiKey: JAGZFIHHGJGTKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  94.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-Trifluoromethanesulfonylsulfanyl-propionic acid ethyl ester 反应 0.67h， 以22%的产率得到ethyl 3-(trifluoromethylthio)propionate
  参考文献：
  名称：

  Synthetic Uses of Thio- and Selenoesters of Trifluoromethylated Acids. 1. Preparation of Trifluoromethyl Sulfides and Selenides

  摘要：

  Trifluorothioacetates (CF3CO-S-R, from (CF3CO)(2)O and thiols) as well as trifluoromethanethio-or trifluoromethaneselenosulfonates (CF3SO2-Y-R; Y = S, Se; from CF3SO2Na, RYYR, and Br-2) can be formally decarbonylated or desulfonylated, respectively, provided that they are photolyzed at 40 degrees C in the presence of 1 equiv of the corresponding disulfide or diselenide. Trifluoromethyl sulfides or selenides are obtained, and the added disulfide (or diselenide) is recovered after reaction. In such a way, S-(trifluoromethyl)cysteine derivatives can be obtained.

  DOI：

  10.1021/jo980649a
• 作为产物：
  描述：

  3,3'-二硫代二(丙酸乙基)酯 、 Langlois reagent 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以88%的产率得到3-Trifluoromethanesulfonylsulfanyl-propionic acid ethyl ester
  参考文献：
  名称：

  A New Route to Thio- and Selenosulfonates from Disulfides and Diselenides. Application to the Synthesis of New Thio- and Selenoesters of Triflic Acid

  摘要：

  Alkyl and aryl trifluoromethanethiosulfonates(1) (or selenosulfonates) were prepared in one step either from alkyl and aryl sulfenyl (or selenenyl) chlorides and sodium trifluoromethanesulfinate (3) or, more generally, from disulfides (or diselenides), 3, and bromine. The second method involved trifluoromethanesulfonyl bromide as key intermediate. Benzenethiosulfonates were obtained in a similar way from disulfides, benzenesulfinate, and bromine but benzeneselenosulfonates could not be obtained by the same method from diselenides.

  DOI：

  10.1021/jo960619c

文献信息

• Addition of trifluoromethanethio- and trifluoromethaneseleno-sulfonates to olefins. Synthesis of vinyl triflones
  作者：Thierry Billard、Bernard R Langlois

  DOI：10.1016/s0040-4020(99)00421-4

  日期：1999.6

  trifluoromethaneselenosulfonates are strong electrophilic reagents which add rapidly to olefins to deliver β-sulfenyl and β-selenyl triflones. These products are converted in high yields to vinyl triflones by different techniques under mild conditions. This two-step procedure is an efficient route to vinyl triflones from non-functionalized olefins.

  三氟甲硫基和三氟甲硒基磺酸盐是很强的亲电试剂，可迅速添加到烯烃中以输送β-亚磺酰基和β-硒烯基三氟甲磺酸酯。在温和的条件下，通过不同的技术将这些产品高产率地转化为乙烯基三氟甲磺酸酯。此两步过程是从非官能化烯烃制备乙烯基三氟乙烯酮的有效途径。