methyl-2,2-dimethyl-3-hydroxy-3-(4-hydroxymethylphenyl)-propionate

• 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: methyl-2,2-dimethyl-3-hydroxy-3-(4-hydroxymethylphenyl)-propionate
• 英文别名: Methyl 3-hydroxy-3-[4-(hydroxymethyl)phenyl]-2,2-dimethylpropanoate；methyl 3-hydroxy-3-[4-(hydroxymethyl)phenyl]-2,2-dimethylpropanoate
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: UJLHKQYQXZHXEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-溴代异丁酸甲酯 、 对苯二甲醇 生成 对羟基甲基苯甲醛 、 methyl-2,2-dimethyl-3-hydroxy-3-(4-hydroxymethylphenyl)-propionate
  参考文献：
  名称：

  Chromium-mediated aldol and homoaldol reactions on solid support directed towards an iterative polyol strategy

  摘要：

  Chromiumn-Reformatsky and chromium-homoaldol reactions run Under neutral and mild reaction conditions. They are highly chemoselective, tolerant towards most common functional groups, and are not prone to retroaldol reactions. Initial studies directed to transfer these homogeneous chromium-mediated solution-phase reactions to solid phase are presented. The main objective was to develop a methodology to aid a combinatorial iterative strategy to polyols (polyketides) on solid phase. A general reactivity problem was observed with polystyrene based resins compared to the solution-phase reactions, independent if the electrophilic (aldehyde) or nucleophilic (bromide) end of the polyol chain was supported to the resin. A complicated penetration, or loss of the polar solvent environment after penetration into the resin, might be responsible for the reduced reactivity. Application of either a soluble polystyrene resin or a polystyrene resin with a polar polyethylene glycol tether resulted in improved yields. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.038

文献信息

• Chromium-mediated aldol and homoaldol reactions on solid support directed towards an iterative polyol strategy
  作者：Ludger A. Wessjohann、Harry Wild、Henri S. Schrekker

  DOI：10.1016/j.tetlet.2004.10.038

  日期：2004.11

  Chromiumn-Reformatsky and chromium-homoaldol reactions run Under neutral and mild reaction conditions. They are highly chemoselective, tolerant towards most common functional groups, and are not prone to retroaldol reactions. Initial studies directed to transfer these homogeneous chromium-mediated solution-phase reactions to solid phase are presented. The main objective was to develop a methodology to aid a combinatorial iterative strategy to polyols (polyketides) on solid phase. A general reactivity problem was observed with polystyrene based resins compared to the solution-phase reactions, independent if the electrophilic (aldehyde) or nucleophilic (bromide) end of the polyol chain was supported to the resin. A complicated penetration, or loss of the polar solvent environment after penetration into the resin, might be responsible for the reduced reactivity. Application of either a soluble polystyrene resin or a polystyrene resin with a polar polyethylene glycol tether resulted in improved yields. (C) 2004 Elsevier Ltd. All rights reserved.