Oxiranecarboxylic acid, 2-(4-chlorobenzoyl)-, methyl ester | 131469-59-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Oxiranecarboxylic acid, 2-(4-chlorobenzoyl)-, methyl ester
• 英文别名: methyl 2-(4-chlorobenzoyl)oxirane-2-carboxylate
• CAS: 131469-59-5
• 化学式: C₁₁H₉ClO₄
• 分子量: 240.643
• InChiKey: ZJWLWJYMTGPGLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Oxiranecarboxylic acid, 2-(4-chlorobenzoyl)-, methyl ester 在 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以47%的产率得到methyl 2-(p-chlorobenzoyloxy)-2-propenoate
  参考文献：
  名称：

  Triphenylphosphine-Mediated Synthesis of Methyl 2-Aroyloxypropenoates from 2-Aroyl-2-methoxycarbonyloxiranes

  摘要：

  A new synthesis of several 2-aroyloxypropenoic acid methyl esters 5 by the reaction of 2-aroyl-2-methoxycarbonyloxiranes 2 with triphenylphosphine in tetrahydrofuran has been described.

  DOI：

  10.1080/00397910902763920
• 作为产物：
  描述：

  4-氯苯甲醛 在 三乙烯二胺 、 sodium hypochlorite 、 silica gel 作用下， 以 乙腈 为溶剂， 反应 74.0h， 生成 Oxiranecarboxylic acid, 2-(4-chlorobenzoyl)-, methyl ester
  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

• Organic reactions in water: an efficient one-pot synthesis of acyloxiranes from Baylis–Hillman adducts using hypervalent iodine
  作者：Biswanath Das、Harish Holla、Katta Venkateswarlu、Anjoy Majhi

  DOI：10.1016/j.tetlet.2005.10.078

  日期：2005.12

  Treatment of Baylis–Hillman adducts with iodosobenzene (PhIO) in the presence of a catalytic amount of KBr in water at room temperature afforded the corresponding acyloxiranes in good yields.

  在室温下在水中以催化量存在KBr的情况下，用碘代苯（PhIO）处理Baylis-Hillman加合物可得到相应的酰氯吡喃，收率很高。
• 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：——
• 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
  作者：André Foucaud、Eliane le Rouillé

  DOI：10.1055/s-1990-27016

  日期：——

  The reaction of sodium hypochlorite with methyl 3-hydroxy-2methylenealkanoates or 3-aryl-3-hydroxy-2-methylenepropanenitriles, dispersed on silica gel, in acetonitrile leads to oxidation of the alcohol function and epoxidation of the methylene group to give 2,2-disubstituted oxiranes in good yield.

  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。
• Triphenylphosphine-Mediated Synthesis of Methyl 2-Aroyloxypropenoates from 2-Aroyl-2-methoxycarbonyloxiranes
  作者：Eun-Gu Han、Kee-Jung Lee

  DOI：10.1080/00397910902763920

  日期：2009.9.8

  A new synthesis of several 2-aroyloxypropenoic acid methyl esters 5 by the reaction of 2-aroyl-2-methoxycarbonyloxiranes 2 with triphenylphosphine in tetrahydrofuran has been described.