1-(4-Methoxyphenyl)propan-2-yl 4-chlorobenzenesulfonate | 134906-48-2

• 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: 1-(4-Methoxyphenyl)propan-2-yl 4-chlorobenzenesulfonate
• 英文别名: 1-(4-methoxyphenyl)propan-2-yl 4-chlorobenzenesulfonate
• CAS: 134906-48-2
• 化学式: C₁₆H₁₇ClO₄S
• 分子量: 340.828
• InChiKey: FFMRGFHNQHWJLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙烷,三氯氟- 、 1-(4-Methoxyphenyl)propan-2-yl 4-chlorobenzenesulfonate 以 甲醇 为溶剂， 生成 N-(1-(4-methoxyphenyl)propan-2-yl)-4-methylaniline
  参考文献：
  名称：

  Cross-interaction constants as a measure of the transition-state structure. 14. Nucleophilic substitution reactions of 1-phenyl-2-propyl benzenesulfonates with anilines in methanol

  摘要：

  The kinetics of the reactions between 1-phenyl-2-propyl benzenesulfonates (PPB) and anilines in methanol at 65.0-degrees-C are investigated, and the mechanism is discussed on the basis of various selectivity parameters, especially on the cross-interaction constants, rho-ij. The aryl participation is significant only with the p-CH3O-substituted substrate. rho-XZ is positive, and accordingly the transition state (TS) variations with substituents are consistent with those predicted by the potential energy surface diagram. The TS is of an intermediate type between that for an associated (tight) and a dissociated (loose) S(N)2 process; it is rather tight, but bond breaking is ahead of bond making with positive charge development at the reaction center in the TS. The possibility of front-side attack with a four-center TS is precluded because of strong steric hinderance in a close approach of the two bulky groups, the nucleophile and leaving group, on the same side in the front-side attack.

  DOI：

  10.1021/jo00015a022

文献信息

• Lee, Ikchoon; Lee, Won Heui; Lee, Hai Whang, Journal of the Chemical Society. Perkin transactions II, 1991, # 5, p. 785 - 791
  作者：Lee, Ikchoon、Lee, Won Heui、Lee, Hai Whang、Lee, Byung Choon

  DOI：——

  日期：——
• Cross-interaction constants as a measure of the transition-state structure. 14. Nucleophilic substitution reactions of 1-phenyl-2-propyl benzenesulfonates with anilines in methanol
  作者：Ikchoon Lee、Won Heui Lee、Hai Whang Lee

  DOI：10.1021/jo00015a022

  日期：1991.7

  The kinetics of the reactions between 1-phenyl-2-propyl benzenesulfonates (PPB) and anilines in methanol at 65.0-degrees-C are investigated, and the mechanism is discussed on the basis of various selectivity parameters, especially on the cross-interaction constants, rho-ij. The aryl participation is significant only with the p-CH3O-substituted substrate. rho-XZ is positive, and accordingly the transition state (TS) variations with substituents are consistent with those predicted by the potential energy surface diagram. The TS is of an intermediate type between that for an associated (tight) and a dissociated (loose) S(N)2 process; it is rather tight, but bond breaking is ahead of bond making with positive charge development at the reaction center in the TS. The possibility of front-side attack with a four-center TS is precluded because of strong steric hinderance in a close approach of the two bulky groups, the nucleophile and leaving group, on the same side in the front-side attack.