Benzenemethanol, 3-chloro-, 1-benzenesulfonate | 135381-99-6

• 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: Benzenemethanol, 3-chloro-, 1-benzenesulfonate
• 英文别名: (3-chlorophenyl)methyl benzenesulfonate
• CAS: 135381-99-6
• 化学式: C₁₃H₁₁ClO₃S
• 分子量: 282.748
• InChiKey: OIFULRSGZBIPDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氰化四乙基铵 、 Benzenemethanol, 3-chloro-, 1-benzenesulfonate 在 4-硝基甲苯 作用下， 以 水 、 乙腈 为溶剂， 生成 间氯氰苄
  参考文献：
  名称：

  Using ¹¹C/¹⁴C Incoming Group and Secondary α-Deuterium KIEs To Determine How a Change in Leaving Group Alters the Structure of the Transition State of the S_N2 Reactions between m-Chlorobenzyl para-Substituted Benzenesulfonates and Cyanide Ion

  摘要：

  The C-11/C-14 incoming group and secondary alpha-deuterium KIEs and Hammett rho value found by changing the substituent in the leaving group of the S(N)2 reactions between meta-chlorobenzyl para-substituted benzenesulfonates and cyanide ion in 0.5% aqueous acetonitrile at 0 degrees C suggest that these reactions occur via an unsymmetrical, product-like transition state. Changing to a better leaving group leads to a transition state with a slightly shorter nucleophile-alpha-carbon bond and a longer alpha-carbon-leaving group bond. The changes in transition state structure are consistent with the Bond Strength Hypothesis.

  DOI：

  10.1021/ja972981u
• 作为产物：
  描述：

  3-氯苯甲醇 、 苯磺酰氯 在 氢氧化钾 作用下， 以 乙醚 为溶剂， 以56%的产率得到Benzenemethanol, 3-chloro-, 1-benzenesulfonate
  参考文献：
  名称：

  Using ¹¹C/¹⁴C Incoming Group and Secondary α-Deuterium KIEs To Determine How a Change in Leaving Group Alters the Structure of the Transition State of the S_N2 Reactions between m-Chlorobenzyl para-Substituted Benzenesulfonates and Cyanide Ion

  摘要：

  The C-11/C-14 incoming group and secondary alpha-deuterium KIEs and Hammett rho value found by changing the substituent in the leaving group of the S(N)2 reactions between meta-chlorobenzyl para-substituted benzenesulfonates and cyanide ion in 0.5% aqueous acetonitrile at 0 degrees C suggest that these reactions occur via an unsymmetrical, product-like transition state. Changing to a better leaving group leads to a transition state with a slightly shorter nucleophile-alpha-carbon bond and a longer alpha-carbon-leaving group bond. The changes in transition state structure are consistent with the Bond Strength Hypothesis.

  DOI：

  10.1021/ja972981u