1-(2-Chloropropan-2-yl)-3,5-dimethylbenzene | 10477-70-0

• 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-(2-Chloropropan-2-yl)-3,5-dimethylbenzene
• CAS: 10477-70-0
• 化学式: C₁₁H₁₅Cl
• 分子量: 182.693
• InChiKey: JJBFWMKGUQLZPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-(2-Chloropropan-2-yl)-3,5-dimethylbenzene 、 三甲基铝 以 正己烷 、 二氯甲烷 为溶剂， 生成 1-叔丁基-3,5-二甲苯
  参考文献：
  名称：

  Access to “Friedel–Crafts-Restricted” tert-Alkyl Aromatics by Activation/Methylation of Tertiary Benzylic Alcohols

  摘要：

  Herein we describe a two-step protocol to prepare m-tert-alkylbenzenes. The appropriate tertiary benzylic alcohols are activated with SOCl2 or concentrated HCl and then treated with trimethylaluminum, affording the desired products in 68-97% yields (22 examples). This reaction sequence is successful in the presence of a variety of functional groups, including acid-sensitive and Lewis-basic groups. In addition to t-Bu groups, 1,1-dimethylpropyl and 1-ethyl-1-methylpropyl groups can also be installed using this method.

  DOI：

  10.1021/jo202371c
• 作为产物：
  描述：

  2-(3,5-xylyl)propan-2-ol 以 吡啶 为溶剂， 反应 22.0h， 以78%的产率得到1-(2-Chloropropan-2-yl)-3,5-dimethylbenzene
  参考文献：
  名称：

  Electronic properties of the nitrone substituent. Stabilization of benzylic carbocations

  摘要：

  The nitrone substituent CH=N(O) t-Bu is electron-withdrawing with a Taft sigma (1) value of 0.20. It also retards the solvolysis rate of a cumyl chloride when placed in the meta-position (sigma (+) = 0.20). However, CH=N(O) t-Bu becomes weakly cation stabilizing when placed in the para-position of a cumyl cation (sigma (+) = -0.04). This weak cation stabilization is a result of a conjugative interaction which delocalizes charge and offsets the inductive effect of the nitrone. When the nitrone is placed in the para-position, but then twisted out of conjugation with the aromatic ring by incorporation of flanking 3,5-dimethyl groups, it again retards solvolysis rates. Computational studies (B3LYP/6-31G*) show that the nitrone substituent stabilizes a para-substituted benzyl cation relative to the meta-substituted analog by a conjugative interaction. However, the calculated stabilization greatly overestimates the cation stabilization seen in solvolytic reactions. Copyright (C) 2001 John Wiley & Sons, Ltd.

  DOI：

  10.1002/1099-1395(200102)14:2<97::aid-poc340>3.0.co;2-2

文献信息

• Byrne, Christopher J.; Happer, Duncan A. R.; Hartshorn, Michael P., Journal of the Chemical Society. Perkin transactions II, 1987, p. 1649 - 1654
  作者：Byrne, Christopher J.、Happer, Duncan A. R.、Hartshorn, Michael P.、Powell, H. Kipton J.

  DOI：——

  日期：——