2-(Benzylsulfonyl)-1-cyclohexanon | 10321-66-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(Benzylsulfonyl)-1-cyclohexanon
• 英文别名: Benzyl-<2-oxo-cyclohexyl>-sulfon；2-Benzylsulfonyl-cyclohexanon-(1)；2-Benzylsulfonyl-cyclohexanon；Benzyl-(2-oxo-cyclohexyl)-sulfon；2-(Phenylmethanesulfonyl)cyclohexan-1-one；2-benzylsulfonylcyclohexan-1-one
• CAS: 10321-66-1
• 化学式: C₁₃H₁₆O₃S
• 分子量: 252.334
• InChiKey: MMDJRWKHXBAGJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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-(Benzylsulfonyl)-1-cyclohexanon 、 sodium hypobromide 、 sodium hydroxide 、 乙醇 生成 6-benzylsulfonyl-6-bromohexanoic acid
  参考文献：
  名称：

  SCHOLZ, D., LIEBIGS ANN. CHEM., 1984, N 2, 264-272

  摘要：

  DOI：
• 作为产物：
  描述：

  环己酮,2-[(苯基甲基)硫代]- 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以98%的产率得到2-(Benzylsulfonyl)-1-cyclohexanon
  参考文献：
  名称：

  Scholz, Dieter, Liebigs Annalen der Chemie, 1984, # 2, p. 264 - 272

  摘要：

  DOI：

文献信息

• 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.
• Shahak,I.; Bergmann,E.D., Israel Journal of Chemistry, 1970, vol. 8, p. 589 - 593
  作者：Shahak,I.、Bergmann,E.D.

  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：——