(ethylsulfanyl)acetyl fluoride | 359794-76-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: (ethylsulfanyl)acetyl fluoride
• 英文别名: 2-(Ethylthio)acetyl fluoride；2-ethylsulfanylacetyl fluoride
• CAS: 359794-76-6
• 化学式: C₄H₇FOS
• 分子量: 122.163
• InChiKey: XFLATGNCHJCCHK-UHFFFAOYSA-N

物化性质

• 沸点：
  154.2±23.0 °C(Predicted)
• 密度：
  1.099±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  异-丙烯基环丙烷 、 (ethylsulfanyl)acetyl fluoride 在 三氟化硼 、 potassium hydrogencarbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.17h， 以82%的产率得到(E)-4-Cyclopropyl-1-ethylsulfanyl-pent-3-en-2-one
  参考文献：
  名称：

  摘要：

  Cyclopropyl-substituted alkenes react with complexes formed by boron trifluoride and 3-(ethylthio)propionyl fluoride and 2-(ethylthio)acetyl fluoride to give ketones containing an ethylthio group. In most cases the reaction is not accompanied by opening of the three-membered ring or rearrangements.

  DOI：

  10.1023/a:1012390420551
• 作为产物：
  描述：

  2-(ethylthio)acetyl chloride 在 potassium hydrogen bifluoride 作用下， 生成 (ethylsulfanyl)acetyl fluoride
  参考文献：
  名称：

  摘要：

  Cyclopropyl-substituted alkenes react with complexes formed by boron trifluoride and 3-(ethylthio)propionyl fluoride and 2-(ethylthio)acetyl fluoride to give ketones containing an ethylthio group. In most cases the reaction is not accompanied by opening of the three-membered ring or rearrangements.

  DOI：

  10.1023/a:1012390420551

文献信息

• Reactions of acylsulfonium salts with unsaturated hydrocarbons
  作者：Valentine G Nenajdenko、Mikhail V Lebedev、Elisabeth S Balenkova

  DOI：10.1016/s0040-4020(01)00897-3

  日期：2001.10

  The reactions of acylsulfonium salts, obtained from β-(ethylsulfanyl)propionyl fluoride and (ethylsulfanyl)acetyl fluoride, with various unsaturated hydrocarbons proceed through the formation of six- and five-membered cyclic sulfonium salts, respectively. Succeeding cleavage of sulfonium salts by bases affords the corresponding sulfur containing unsaturated ketones.

  由β-（乙基硫烷基）丙酰氟和（乙基硫烷基）乙酰氟形成的酰基ulf盐与各种不饱和烃的反应分别通过六元和五元环状sulf盐的形成而进行。用碱成功裂解sulf盐得到相应的含硫不饱和酮。
• A New Synthetic Approach to Thiophenes
  作者：Mikhail V. Lebedev、Valentine G. Nenajdenko、Elizabeth S. Balenkova

  DOI：10.1055/s-2001-18054

  日期：——

  A new simple and efficient way to 3-hydroxy(methoxy)thiophenes is described. The reactions of (ethylsulfanyl)acetyl fluoride/boron trifluoride (1) and 2-(ethylsulfanyl)butanoyl fluoride/boron trifluoride (6) complexes with acetylenes give rise to the 5-membered cyclic sulfonium salts (3a-f). The last ones (3e, 3f) after being refluxed with thiourea in methanol or acetonitrile are converted into 3-methoxythiophenes or 3-(2H)-thiophenones respectively. Several 3-methoxythiophenes unsubstituted in the 2-position were obtained by the reactions of 1 with acetylenes. Reactions of 6 with acetylenes allows the synthesis of 2-ethylsubsituted 3-methoxythiophenes. The method allows the synthesis of a variety of mono-, di-, tri- and tetrasubsituted thiophenes.

  本文介绍了一种制备 3-羟基（甲氧基）噻吩的简单而有效的新方法。(乙基硫酰基)乙酰氟化物/三氟化硼 (1) 和 2-(乙基硫酰基)丁酰氟/三氟化硼 (6) 复合物与乙炔的反应生成 5 元环锍盐 (3a-f)。最后一种（3e、3f）在甲醇或乙腈中与硫脲回流后，分别转化为 3-甲氧基噻吩或 3-(2H)-噻吩酮。通过 1 与乙炔的反应，可以得到几种 2 位未取代的 3-甲氧基噻吩。6 与乙炔的反应可以合成 2-乙基取代的 3-甲氧基噻吩。这种方法可以合成各种单取代、二取代、三取代和四取代的噻吩。
• ——
  作者：M. V. Lebedev、V. G. Nenaidenko、K. I. Smolko、E. S. Balenkova

  DOI：10.1023/a:1012390420551

  日期：——

  Cyclopropyl-substituted alkenes react with complexes formed by boron trifluoride and 3-(ethylthio)propionyl fluoride and 2-(ethylthio)acetyl fluoride to give ketones containing an ethylthio group. In most cases the reaction is not accompanied by opening of the three-membered ring or rearrangements.