5-(deuteriomethyl)-1,3-dimethoxy-2-methylbenzene | 1361954-86-0

• 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: 5-(deuteriomethyl)-1,3-dimethoxy-2-methylbenzene
• CAS: 1361954-86-0
• 化学式: C₁₀H₁₄O₂
• 分子量: 167.212
• InChiKey: GIUXLBFXMAOOQJ-MICDWDOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3,5-二甲氧基甲苯 在 2,2,6,6-四甲基哌啶 、 正丁基锂 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 正己烷 、 环己烷 为溶剂， 反应 1.5h， 生成 5-(deuteriomethyl)-1,3-dimethoxy-2-methylbenzene
  参考文献：
  名称：

  Homo- and Hetero-oxidative Coupling of Benzyl Anions

  摘要：

  The regioselective benzylic metalation of substituted toluenes using BuLi/KO-t-Bu/TMP(H) (LiNK metalation conditions) with subsequent in situ oxidative C-C coupling has been developed for the facile generation of 1,2-diarylethanes. A range of oxidants can be used for the oxidative coupling step, with 1,2-dibromoethane proving optimal. Heterocouplings can be achieved starting from a mixture of two different toluenes with a bias toward cross coupling achievable by using a 2-fold excess of one toluene starting material. The utility of this approach is illustrated by the synthesis of several biologically active natural products. A distinct advantage is that the synthetic steps typically required to preactivate the coupling substrates are eliminated and no transition metal is required to facilitate the C-C bond formation.

  DOI：

  10.1021/jo3000805

文献信息

• Homo- and Hetero-oxidative Coupling of Benzyl Anions
  作者：Marco Blangetti、Patricia Fleming、Donal F. O’Shea

  DOI：10.1021/jo3000805

  日期：2012.3.16

  The regioselective benzylic metalation of substituted toluenes using BuLi/KO-t-Bu/TMP(H) (LiNK metalation conditions) with subsequent in situ oxidative C-C coupling has been developed for the facile generation of 1,2-diarylethanes. A range of oxidants can be used for the oxidative coupling step, with 1,2-dibromoethane proving optimal. Heterocouplings can be achieved starting from a mixture of two different toluenes with a bias toward cross coupling achievable by using a 2-fold excess of one toluene starting material. The utility of this approach is illustrated by the synthesis of several biologically active natural products. A distinct advantage is that the synthetic steps typically required to preactivate the coupling substrates are eliminated and no transition metal is required to facilitate the C-C bond formation.