2,2-dimethylcyclopentyl brosylate | 94844-04-9

• 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: 2,2-dimethylcyclopentyl brosylate
• 英文别名: (2,2-Dimethylcyclopentyl) 4-bromobenzenesulfonate；(2,2-dimethylcyclopentyl) 4-bromobenzenesulfonate
• CAS: 94844-04-9
• 化学式: C₁₃H₁₇BrO₃S
• 分子量: 333.246
• InChiKey: JKDCLQFUHGPYTI-UHFFFAOYSA-N

物化性质

• 沸点：
  392.3±25.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  rac-2,2-二甲基环戊醇 、 4-溴苯磺酰氯 在 吡啶 作用下， 生成 2,2-dimethylcyclopentyl brosylate
  参考文献：
  名称：

  Hydrogen participation in the solvolysis of 2-methylcyclopentyl arenesulfonates

  摘要：

  Solvolysis of cis- and trans-2-methylcyclopentyl arenesulfonates has been examined in several ethanol-water, trifluoroethanol-water, and hexafluoroisopropyl alcohol-water mixtures. Rates, alpha-d and beta-d kinetic isotope effects, and product yields have been determined. The results indicate that cis-2-methylcyclopentyl p-toluenesulfonate reacts with rate-determining hydrogen participation after reversible formation of the intimate ion pair. In contrast, trans-2-methylcyclopentyl p-bromobenzenesulfonate reacts by varying proportions of rate-determining solvent nucleophilic attack, solvent-promoted elimination, and ion pair separation after reversible formation of the intimate ion pair. The details of these mechanisms are quantitatively described with the aid of a steady state analysis, and the results are correlated with the mechanisms previously proposed for cyclopentyl brosylate and 2,2-dimethylcyclopentyl brosylate.

  DOI：

  10.1021/jo00011a019

文献信息

• Hydrogen participation in the solvolysis of 2-methylcyclopentyl arenesulfonates
  作者：Michael A. Imhoff、R. Michael Ragain、Kimberly Moore、V. J. Shiner

  DOI：10.1021/jo00011a019

  日期：1991.5

  Solvolysis of cis- and trans-2-methylcyclopentyl arenesulfonates has been examined in several ethanol-water, trifluoroethanol-water, and hexafluoroisopropyl alcohol-water mixtures. Rates, alpha-d and beta-d kinetic isotope effects, and product yields have been determined. The results indicate that cis-2-methylcyclopentyl p-toluenesulfonate reacts with rate-determining hydrogen participation after reversible formation of the intimate ion pair. In contrast, trans-2-methylcyclopentyl p-bromobenzenesulfonate reacts by varying proportions of rate-determining solvent nucleophilic attack, solvent-promoted elimination, and ion pair separation after reversible formation of the intimate ion pair. The details of these mechanisms are quantitatively described with the aid of a steady state analysis, and the results are correlated with the mechanisms previously proposed for cyclopentyl brosylate and 2,2-dimethylcyclopentyl brosylate.