Methyl 2-bromo-2-(hydroxymethyl)-3-(4-methoxyphenyl)-3-oxopropanoate | 1123134-84-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 2-bromo-2-(hydroxymethyl)-3-(4-methoxyphenyl)-3-oxopropanoate
• 英文别名: methyl 2-bromo-2-(hydroxymethyl)-3-(4-methoxyphenyl)-3-oxopropanoate
• CAS: 1123134-84-8
• 化学式: C₁₂H₁₃BrO₅
• 分子量: 317.136
• InChiKey: FNHPGYAEGNFEHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 2-bromo-2-(hydroxymethyl)-3-(4-methoxyphenyl)-3-oxopropanoate 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.13h， 以84%的产率得到Methyl 2-(4-methoxybenzoyl)oxirane-2-carboxylate
  参考文献：
  名称：

  IBX/LiBr-promoted one-pot oxidative anti-Markownikov bromohydroxylation/bromoalkoxylation of Baylis–Hillman olefins

  摘要：

  The first example of one-pot oxidative anti-Markownikov bromohydroxylation and bromoalkoxylation of Baylis-Hillman (BH) adducts (olefins) is reported. The reaction is performed at rt using LiBr as the bromine source and 2-iodoxybenzoic acid (IBX) as the oxidant. The process involves oxidation of BH adducts with IBX to give beta-ketomethylene compounds in situ, which undergo highly regioselective vicinal functionalization with LiBr/H2O or LiBr/ROH in the same vessel to afford of alpha-bromo-beta-hydroxy or alpha-bromo-beta-alkoxy compounds, respectively, in excellent yields. The alpha-bromo-beta-hydroxy Compounds are readily transformed into epoxides in aq NaOH. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.11.119
• 作为产物：
  描述：

  methyl 2-(4-methoxybenzoyl)acrylate 在 水 、 lithium bromide 作用下， 以 乙腈 为溶剂， 反应 10.0h， 生成 Methyl 2-bromo-2-(hydroxymethyl)-3-(4-methoxyphenyl)-3-oxopropanoate
  参考文献：
  名称：

  IBX/LiBr-promoted one-pot oxidative anti-Markownikov bromohydroxylation/bromoalkoxylation of Baylis–Hillman olefins

  摘要：

  The first example of one-pot oxidative anti-Markownikov bromohydroxylation and bromoalkoxylation of Baylis-Hillman (BH) adducts (olefins) is reported. The reaction is performed at rt using LiBr as the bromine source and 2-iodoxybenzoic acid (IBX) as the oxidant. The process involves oxidation of BH adducts with IBX to give beta-ketomethylene compounds in situ, which undergo highly regioselective vicinal functionalization with LiBr/H2O or LiBr/ROH in the same vessel to afford of alpha-bromo-beta-hydroxy or alpha-bromo-beta-alkoxy compounds, respectively, in excellent yields. The alpha-bromo-beta-hydroxy Compounds are readily transformed into epoxides in aq NaOH. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.11.119

文献信息

• IBX/LiBr-promoted one-pot oxidative anti-Markownikov bromohydroxylation/bromoalkoxylation of Baylis–Hillman olefins
  作者：Lal Dhar S. Yadav、Chhama Awasthi

  DOI：10.1016/j.tetlet.2008.11.119

  日期：2009.2

  The first example of one-pot oxidative anti-Markownikov bromohydroxylation and bromoalkoxylation of Baylis-Hillman (BH) adducts (olefins) is reported. The reaction is performed at rt using LiBr as the bromine source and 2-iodoxybenzoic acid (IBX) as the oxidant. The process involves oxidation of BH adducts with IBX to give beta-ketomethylene compounds in situ, which undergo highly regioselective vicinal functionalization with LiBr/H2O or LiBr/ROH in the same vessel to afford of alpha-bromo-beta-hydroxy or alpha-bromo-beta-alkoxy compounds, respectively, in excellent yields. The alpha-bromo-beta-hydroxy Compounds are readily transformed into epoxides in aq NaOH. (C) 2008 Elsevier Ltd. All rights reserved.