1-deuterio-2-methoxy-4-methylbenzene | 1266251-90-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-deuterio-2-methoxy-4-methylbenzene
• CAS: 1266251-90-4
• 化学式: C₈H₁₀O
• 分子量: 123.159
• InChiKey: OSIGJGFTADMDOB-UICOGKGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  间甲基苯甲醚 在 正丁基锂 、 potassium tert-butylate 、 氘代甲醇 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 1-deuterio-2-methoxy-4-methylbenzene 、 1-methoxy-3-deuteriomethylbenzene
  参考文献：
  名称：

  Controlled Anion Migrations with a Mixed Metal Li/K-TMP Amide: General Application to Benzylic Metalations

  摘要：

  A general method is described for benzylic metalation of o-, m-, and p-substituted toluenes using a mixed metal amide base generated from BuLi/KOtBu/TMP at -78 degrees C in THF. The excellent selectivity achieved can be rationalized by the ability of the mixed metal amide base to facilitate an anion migration from the kinetic (o-aryl) to the benzylic metalation site. Remarkably, this controlled anion migration is achievable with catalytic amounts of TMP at -78 degrees C.

  DOI：

  10.1021/ja110234v

文献信息

• Controlled Anion Migrations with a Mixed Metal Li/K-TMP Amide: General Application to Benzylic Metalations
  作者：Patricia Fleming、Donal F. O’Shea

  DOI：10.1021/ja110234v

  日期：2011.2.16

  A general method is described for benzylic metalation of o-, m-, and p-substituted toluenes using a mixed metal amide base generated from BuLi/KOtBu/TMP at -78 degrees C in THF. The excellent selectivity achieved can be rationalized by the ability of the mixed metal amide base to facilitate an anion migration from the kinetic (o-aryl) to the benzylic metalation site. Remarkably, this controlled anion migration is achievable with catalytic amounts of TMP at -78 degrees C.