S-(2,2,2-trifluoroethyl) 2-methylprop-2-ene-1-sulfothioate | 847661-08-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: S-(2,2,2-trifluoroethyl) 2-methylprop-2-ene-1-sulfothioate
• 英文别名: Msopipltsfiicf-uhfffaoysa-；2-methyl-3-(2,2,2-trifluoroethylsulfanylsulfonyl)prop-1-ene
• CAS: 847661-08-9
• 化学式: C₆H₉F₃O₂S₂
• 分子量: 234.263
• InChiKey: MSOPIPLTSFIICF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  对甲基苯甲醛 、 S-(2,2,2-trifluoroethyl) 2-methylprop-2-ene-1-sulfothioate 在 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 2.0h， 生成 1-methyl-4-[(1Z)-3-methylbuta-1,3-dienyl]benzene 、 (E)-1-methyl-4-(3-methylbuta-1,3-dien-1-yl)benzene
  参考文献：
  名称：

  One-pot synthesis of 1-aryl-3-methyl-1,3-dienes using methallyl(trimethyl)silane and aldehydes and their low temperature (Z)→(E) isomerization induced by sulfur dioxide

  摘要：

  2-Methylprop-2-ene-1-sulfonyl fluorides can be easily prepared via the ene reaction of methallylsilanes and SO2. In the presence of a base, aldehydes and 2-methylprop-2-ene-1-sulfonyl fluorides give 1.3-(E) and (Z)-dienes. Their (Z) --> (E) isomerization by classical means fails or leads to their polymerization. It is shown that SO, can isomerize 1-aryl-3-methyl-1.3-dienes at low temperature, without formation of sulfolenes (cheletropic addition/elimination). Preliminary mechanistic studies suggest that SO2 adds to 1.3-dienes forming 1,4-diradical intermediates that are responsible for the (Z)-->(E) isomerizations. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.11.070
• 作为产物：
  描述：

  methallylsulfonyl chloride 、 2,2,2-三氟乙硫醇 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以50%的产率得到S-(2,2,2-trifluoroethyl) 2-methylprop-2-ene-1-sulfothioate
  参考文献：
  名称：

  One-pot synthesis of 1-aryl-3-methyl-1,3-dienes using methallyl(trimethyl)silane and aldehydes and their low temperature (Z)→(E) isomerization induced by sulfur dioxide

  摘要：

  2-Methylprop-2-ene-1-sulfonyl fluorides can be easily prepared via the ene reaction of methallylsilanes and SO2. In the presence of a base, aldehydes and 2-methylprop-2-ene-1-sulfonyl fluorides give 1.3-(E) and (Z)-dienes. Their (Z) --> (E) isomerization by classical means fails or leads to their polymerization. It is shown that SO, can isomerize 1-aryl-3-methyl-1.3-dienes at low temperature, without formation of sulfolenes (cheletropic addition/elimination). Preliminary mechanistic studies suggest that SO2 adds to 1.3-dienes forming 1,4-diradical intermediates that are responsible for the (Z)-->(E) isomerizations. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.11.070

文献信息

• One-pot synthesis of 1-aryl-3-methyl-1,3-dienes using methallyl(trimethyl)silane and aldehydes and their low temperature (Z)→(E) isomerization induced by sulfur dioxide
  作者：Srinivas Reddy Dubbaka、Pierre Vogel

  DOI：10.1016/j.tet.2004.11.070

  日期：2005.2

  2-Methylprop-2-ene-1-sulfonyl fluorides can be easily prepared via the ene reaction of methallylsilanes and SO2. In the presence of a base, aldehydes and 2-methylprop-2-ene-1-sulfonyl fluorides give 1.3-(E) and (Z)-dienes. Their (Z) --> (E) isomerization by classical means fails or leads to their polymerization. It is shown that SO, can isomerize 1-aryl-3-methyl-1.3-dienes at low temperature, without formation of sulfolenes (cheletropic addition/elimination). Preliminary mechanistic studies suggest that SO2 adds to 1.3-dienes forming 1,4-diradical intermediates that are responsible for the (Z)-->(E) isomerizations. (C) 2004 Elsevier Ltd. All rights reserved.

表征谱图