2-methylprop-2-ene-1-sulfonyl fluoride | 847661-06-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 磺酰卤
• 英文名称: 2-methylprop-2-ene-1-sulfonyl fluoride
• 英文别名: Fikvhxrifmbppl-uhfffaoysa-
• CAS: 847661-06-7
• 化学式: C₄H₇FO₂S
• 分子量: 138.163
• InChiKey: FIKVHXRIFMBPPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-甲氧基苯甲醛 、 2-methylprop-2-ene-1-sulfonyl fluoride 在 potassium carbonate 作用下， 以40%的产率得到(E)-1-methoxy-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 在 potassium fluoride 、 二苯并-18-冠醚-6 作用下， 以80%的产率得到2-methylprop-2-ene-1-sulfonyl fluoride
  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

• A regio- and stereoselective Heck–Matsuda process for construction of γ-aryl allylsulfonyl fluorides
  作者：Hao-Yong Qin、Houying Gui、Zai-Wei Zhang、Tao Shu、Hua-Li Qin

  DOI：10.1039/d2ra03733e

  日期：——

  A Heck–Matsuda reaction of aryl diazoniums with allylsulfonyl fluorides for the construction of γ-aryl allylsulfonyl fluorides was developed.

  开发了芳基重氮鎓与烯丙基磺酰氟的 Heck-Matsuda 反应，以生成 γ-芳基烯丙基磺酰氟。
• 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