2-methoxy-6-(methoxymethyl)phenyllithium

• 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: 2-methoxy-6-(methoxymethyl)phenyllithium
• 化学式: C₉H₁₁LiO₂
• 分子量: 158.126
• InChiKey: UGBMDNMRUYCKME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.26
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methoxy-6-(methoxymethyl)phenyllithium 、 乙炔基磺酰苯 生成 lithium (phenylsulfonyl)acetylide
  参考文献：
  名称：

  Reactivity of Individual Organolithium Aggregates:  A RINMR Study of n-Butyllithium and 2-Methoxy-6-(methoxymethyl)phenyllithium

  摘要：

  Low-temperature rapid injection NMR (RINMR) experiments were performed on two lithium reagents, n-butyllithium and 2-methoxy-6-(methoxymethyl) phenyllithium ( 5), with the goal of measuring the relative reactivity of the different aggregates ( dimer, mixed dimer, and tetramer for n-BuLi, monomer and tetramer for 5) toward typical electrophiles. The reaction of the n-BuLi dimer with ( trimethylsilyl) acetylene first forms the mixed dimer n-(BuLiMe3SiC)-Me-. CLi, which is about 1/60 as reactive as the n-BuLi homodimer. The tetramer does not react. In the deprotonation of (phenylthio) acetylene, the n-BuLi dimer was found to be 3.5 x 10(8) as reactive as the tetramer, and in the addition to p-diethylaminobenzaldehyde, the relative reactivity was at least 2 x 10(4). In the deprotonation of (p-tolylsulfonyl) acetylene, the monomer of 5 was at least 1014 times as reactive as the tetramer. These measurements show that the difference in reactivity between the lower and higher aggregates of organolithium reagents can be many orders of magnitude higher than all previous estimates.

  DOI：

  10.1021/ja0689334
• 作为产物：
  描述：

  间甲氧基苯甲醇 在 正丁基锂 、 sodium hydride 作用下， 以 正己烷 、 二甲基亚砜 、 正戊烷 为溶剂， 反应 7.0h， 生成 2-methoxy-6-(methoxymethyl)phenyllithium
  参考文献：
  名称：

  Reactivity of Individual Organolithium Aggregates:  A RINMR Study of n-Butyllithium and 2-Methoxy-6-(methoxymethyl)phenyllithium

  摘要：

  Low-temperature rapid injection NMR (RINMR) experiments were performed on two lithium reagents, n-butyllithium and 2-methoxy-6-(methoxymethyl) phenyllithium ( 5), with the goal of measuring the relative reactivity of the different aggregates ( dimer, mixed dimer, and tetramer for n-BuLi, monomer and tetramer for 5) toward typical electrophiles. The reaction of the n-BuLi dimer with ( trimethylsilyl) acetylene first forms the mixed dimer n-(BuLiMe3SiC)-Me-. CLi, which is about 1/60 as reactive as the n-BuLi homodimer. The tetramer does not react. In the deprotonation of (phenylthio) acetylene, the n-BuLi dimer was found to be 3.5 x 10(8) as reactive as the tetramer, and in the addition to p-diethylaminobenzaldehyde, the relative reactivity was at least 2 x 10(4). In the deprotonation of (p-tolylsulfonyl) acetylene, the monomer of 5 was at least 1014 times as reactive as the tetramer. These measurements show that the difference in reactivity between the lower and higher aggregates of organolithium reagents can be many orders of magnitude higher than all previous estimates.

  DOI：

  10.1021/ja0689334

文献信息

• Reactivity of Individual Organolithium Aggregates:  A RINMR Study of <i>n</i>-Butyllithium and 2-Methoxy-6-(methoxymethyl)phenyllithium
  作者：Amanda C. Jones、Aaron W. Sanders、Martin J. Bevan、Hans J. Reich

  DOI：10.1021/ja0689334

  日期：2007.3.1

  Low-temperature rapid injection NMR (RINMR) experiments were performed on two lithium reagents, n-butyllithium and 2-methoxy-6-(methoxymethyl) phenyllithium ( 5), with the goal of measuring the relative reactivity of the different aggregates ( dimer, mixed dimer, and tetramer for n-BuLi, monomer and tetramer for 5) toward typical electrophiles. The reaction of the n-BuLi dimer with ( trimethylsilyl) acetylene first forms the mixed dimer n-(BuLiMe3SiC)-Me-. CLi, which is about 1/60 as reactive as the n-BuLi homodimer. The tetramer does not react. In the deprotonation of (phenylthio) acetylene, the n-BuLi dimer was found to be 3.5 x 10(8) as reactive as the tetramer, and in the addition to p-diethylaminobenzaldehyde, the relative reactivity was at least 2 x 10(4). In the deprotonation of (p-tolylsulfonyl) acetylene, the monomer of 5 was at least 1014 times as reactive as the tetramer. These measurements show that the difference in reactivity between the lower and higher aggregates of organolithium reagents can be many orders of magnitude higher than all previous estimates.