4-<(4'-methylbenzenesulfonyl)oxy>-4-(4''-nitrophenyl)butan-2-one | 225092-51-3

• 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: 4-<(4'-methylbenzenesulfonyl)oxy>-4-(4''-nitrophenyl)butan-2-one
• 英文别名: 4-<(4'-methylbenzenesulfonyl)oxy>-4-(4"-nitrophenyl)butan-2-one
• CAS: 225092-51-3
• 化学式: C₁₇H₁₇NO₆S
• 分子量: 363.391
• InChiKey: DZAKKQJJDRXSJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  103.58
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-<(4'-methylbenzenesulfonyl)oxy>-4-(4''-nitrophenyl)butan-2-one 在 三乙烯二胺 作用下， 以 甲醇 为溶剂， 生成 对硝基苄叉丙酮
  参考文献：
  名称：

  Mechanisms of elimination and substitution reactions. Spontaneous solvolysis reactions via carbanion and carbocation intermediates

  摘要：

  The reactions of 4-(4'-nitrophenyl)-4-X-butan-2-one (1-X; X = Cl, OTs) with added bases/nucleophiles exhibit second-order kinetics. These substitution and elimination reactions are concluded to be of concerted S(N)2 type and irreversible E1cB type, respectively. The spontaneous formation of alkene from the chloride L-CI is suggested to occur by a water-promoted E1cB reaction. The fraction of elimination product is smaller with the tosylate 1-OTs. It is plausible that the elimination and substitution reactions of 1-OTs are carbocation reactions since the Bronsted plot with substituted acetate anion bases shows a tenfold positive deviation for the 'water-catalyzed' elimination reaction, and there is a trace of substitution reaction with the acetonitrile component of the solvent yielding 1-NHCOMe. These results are consistent with a common, very short-lived, carbocation intermediate. Copyright (C) 1999 John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1099-1395(199902)12:2<116::aid-poc102>3.0.co;2-8
• 作为产物：
  描述：

  1-(4-硝基苯基)-3-氧代-1-丁醇 、 对甲苯磺酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 4-<(4'-methylbenzenesulfonyl)oxy>-4-(4''-nitrophenyl)butan-2-one
  参考文献：
  名称：

  Mechanisms of elimination and substitution reactions. Spontaneous solvolysis reactions via carbanion and carbocation intermediates

  摘要：

  The reactions of 4-(4'-nitrophenyl)-4-X-butan-2-one (1-X; X = Cl, OTs) with added bases/nucleophiles exhibit second-order kinetics. These substitution and elimination reactions are concluded to be of concerted S(N)2 type and irreversible E1cB type, respectively. The spontaneous formation of alkene from the chloride L-CI is suggested to occur by a water-promoted E1cB reaction. The fraction of elimination product is smaller with the tosylate 1-OTs. It is plausible that the elimination and substitution reactions of 1-OTs are carbocation reactions since the Bronsted plot with substituted acetate anion bases shows a tenfold positive deviation for the 'water-catalyzed' elimination reaction, and there is a trace of substitution reaction with the acetonitrile component of the solvent yielding 1-NHCOMe. These results are consistent with a common, very short-lived, carbocation intermediate. Copyright (C) 1999 John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1099-1395(199902)12:2<116::aid-poc102>3.0.co;2-8