2,2,4,4-tetramethyl-3-pyrrolidinothietane 1,1-dioxide | 4798-87-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2,2,4,4-tetramethyl-3-pyrrolidinothietane 1,1-dioxide
• 英文别名: 3-Pyrrolidino-2.2.4.4-tetramethyl-thietan-1.1-dioxid；2,2,4,4-Tetramethyl-3-pyrrolidin-1-ylthietane 1,1-dioxide
• CAS: 4798-87-2
• 化学式: C₁₁H₂₁NO₂S
• 分子量: 231.359
• InChiKey: FTLCEBWTHLRIJN-UHFFFAOYSA-N

物化性质

• 熔点：
  111 °C
• 沸点：
  342.1±35.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  异丙基磺酰氯 、 1-(2-甲基-1-丙烯基)吡咯烷 在 sodium hydroxide 作用下， 以 乙二醇二甲醚 为溶剂， 以31%的产率得到1-(2-propylsulfonyl)pyrrolidine
  参考文献：
  名称：

  Organic sulfur mechanisms. 37. Mechanisms of hydrolysis of (trimethylsilyl)methanesulfonyl chloride. Sulfene-enamine reactions in water

  摘要：

  Kinetic, product analysis, and deuteration experiments are consistent with the following mechanisms of hydrolysis of (trimethylsilyl)methanesulfonyl chloride (1) (in 0.01 M KCl at 1-degrees-C): (a) pH less-than-or-equal-to 10.0, attack of water at silicon to form sulfene (5) which is trapped by water to give methanesulfonate anion (3), (b) pH greater-than-or-equal-to 10.0, attack of hydroxide anion (i) at silicon to yield sulfene (5) and (ii) at an alpha-hydrogen to form (trimethylsilyl)sulfene (4), in each case followed by trapping of the sulfene to give either methanesulfonate (3) or (trimethylsilyl)methanesulfonate (6) salts. Aqueous potassium fluoride catalyzes the hydrolysis of 1 with formation of the methanesulfonate 3, evidently by way of silicophilic attack of fluoride anion on 1 with formation of sulfene (5). Reaction of 1 with an enamine 7 in water (at pH 8 or 9), with or without fluoride, gives two characteristic sulfene-enamine products, (i) the four-membered cycloadduct 8 and (ii) the methylsulfonyl aldehyde 9. The same or related products are also obtained from methanesulfonyl, 2-propanesulfonyl, and phenylmethanesulfonyl chlorides and enamines in water (at pH 9). Hydrolysis of 1 is also catalyzed by aniline or triethylamine evidently giving 5.

  DOI：

  10.1021/jo00064a037