2-(甲基磺酰基)-1-环己酮 | 16096-71-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 中文名称: 2-(甲基磺酰基)-1-环己酮
• 英文名称: 2-(Methylsulfonyl)-1-cyclohexanon
• 英文别名: 2-(methylsulfonyl)cyclohexanone；2-(Methylsulfonyl)cyclohexanon；α-Methylsulfonylcyclohexanon；2-Methylsulfonyl-cyclohexanon-(1)；2-methanesulfonyl-cyclohexanone；2-Methansulfonyl-cyclohexanon；2-Methylsulfon-cyclohexanon；2-Methanesulfonylcyclohexan-1-one；2-methylsulfonylcyclohexan-1-one
• CAS: 16096-71-2
• 化学式: C₇H₁₂O₃S
• mdl: MFCD15209655
• 分子量: 176.236
• InChiKey: KILKRQFHFYYRNM-UHFFFAOYSA-N

物化性质

• 熔点：
  57-58 °C(Solv: ligroine (8032-32-4))
• 沸点：
  377.5±31.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.857
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(甲基磺酰基)-1-环己酮 在 L-Selectride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以79%的产率得到cis-2-(methylsulfonyl)cyclohexanol
  参考文献：
  名称：

  Studies on the stereoselectivity of hydride reductions on 2-(methylthio)- and 2-(methylsulfonyl)cyclohexanones

  摘要：

  DOI：

  10.1021/jo00392a022
• 作为产物：
  描述：

  2-溴环己酮 在 双氧水 、 乙酸酐 、 溶剂黄146 作用下， 生成 2-(甲基磺酰基)-1-环己酮
  参考文献：
  名称：

  The Preparation of β-Keto Sulfones by the Claisen Condensation¹

  摘要：

  DOI：

  10.1021/ja01624a037

文献信息

• Transition-metal-free insertion of alkynes into the C–C σ-bond of cyclic β-keto sulfones: an atom-economical way to medium-size-ring sulfonyl derivatives
  作者：Yingge Gu、Yajie Yang、Ye Wang、Zongkang Wang、Yilin Zhu、Yanzhong Li

  DOI：10.1039/d2nj01197b

  日期：——

  efficient strategy for the preparation of medium-size-ring sulfonyl derivatives has been developed. This method is realized by alkynes insertion into the C–C σ-bond of cyclic β-keto sulfones, introducing sulfonyl groups into medium-size-ring compounds. This reaction possesses competitive features such as broad substrate scope, transition-metal-free and atom economy.

  已经开发了一种新型的碱促进和高效的制备中等尺寸环磺酰基衍生物的策略。该方法是通过将炔烃插入环状 β-酮砜的 C-C σ-键中，将磺酰基引入到中等大小的环状化合物中来实现的。该反应具有底物范围广、不含过渡金属、原子经济等竞争特点。
• Organic sulfur mechanisms. 37. Mechanisms of hydrolysis of (trimethylsilyl)methanesulfonyl chloride. Sulfene-enamine reactions in water
  作者：James F. King、Joe Y. L. Lam

  DOI：10.1021/jo00064a037

  日期：1993.6

  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.
• Scholz, Dieter, Liebigs Annalen der Chemie, 1983, # 1, p. 98 - 106
  作者：Scholz, Dieter

  DOI：——

  日期：——
• Scholz, Dieter, Liebigs Annalen der Chemie, 1984, # 2, p. 264 - 272
  作者：Scholz, Dieter

  DOI：——

  日期：——
• SCHOLZ, D., LIEBIGS ANN. CHEM., 1984, N 2, 264-272
  作者：SCHOLZ, D.

  DOI：——

  日期：——