Methyl 2-(4-methoxybenzoyl)oxirane-2-carboxylate | 131469-61-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Methyl 2-(4-methoxybenzoyl)oxirane-2-carboxylate
• CAS: 131469-61-9
• 化学式: C₁₂H₁₂O₅
• 分子量: 236.224
• InChiKey: NFZTWIHYAHOPSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 2-[hydroxy(4-methoxyphenyl)methyl]prop-2-enoate 在 sodium hypochlorite 、 silica gel 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以85%的产率得到Methyl 2-(4-methoxybenzoyl)oxirane-2-carboxylate
  参考文献：
  名称：

  One-Pot Preparation of 1-Acyl-1-methoxycarbonyloxiranes and 1-Acyl-1-cyanooxiranes from Methyl 3-Hydroxy-2-methylenealkanoates or 3-Aryl-3-hydroxy-2-methylenepropanenitriles

  摘要：

  次氯酸钠与甲基3-羟基-2-亚甲基烷酸酯或3-芳基-3-羟基-2-亚甲基丙腈在硅胶上分散，并在乙腈中反应，导致醇功能被氧化，亚甲基被环氧化，从而以良好产率得到2,2-二取代的环氧乙烷。

  DOI：

  10.1055/s-1990-27016

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.
• FOUCAUD, ANDRE;LE, ROUILLE ELIANE, SYNTHESIS (BRD),(1990) N, C. 787-789
  作者：FOUCAUD, ANDRE、LE, ROUILLE ELIANE

  DOI：——

  日期：——