Methyl (Z)-3-(Benzoyloxy)-2-butenoate | 93530-71-3

• 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 (Z)-3-(Benzoyloxy)-2-butenoate
• 英文别名: (Z)-4-methoxy-4-oxobuten-2-yl benzoate；(Z)-4-methoxy-4-oxobut-2-en-2-yl benzoate；[(Z)-4-methoxy-4-oxobut-2-en-2-yl] benzoate
• CAS: 93530-71-3
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: WZFAHVQUOFYFPP-HJWRWDBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl (Z)-3-(Benzoyloxy)-2-butenoate 在 Wilkinson's catalyst 氘 作用下， 以 苯 为溶剂， 40.0 ℃ 、1.03 MPa 条件下， 反应 24.0h， 以73%的产率得到Methyl (R,R)- and (S,S)-3-(benzyloxy)<2,3-²H2>butanoate
  参考文献：
  名称：

  Stereospecific synthesis of 2-deuterio-3-hydroxybutanoate esters. Regiochemistry and stereochemistry of homogeneous hydrogenation with Wilkinson's catalyst

  摘要：

  DOI：

  10.1021/jo00200a033
• 作为产物：
  描述：

  苯甲醛 、 乙酰乙酸甲酯 在 叔丁基过氧化氢 、 copper(I) bromide 作用下， 以 癸烷 为溶剂， 反应 16.0h， 以84%的产率得到Methyl (Z)-3-(Benzoyloxy)-2-butenoate
  参考文献：
  名称：

  Highly Stereoselective Oxidative Esterification of Aldehydes with β-Dicarbonyl Compounds

  摘要：

  Copper-catalyzed oxidative esterification of aldehydes with beta-dicarbonyl compounds was developed using tert-butyl hydroperoxide as an oxidant. In general, the enol esters were synthesized in good yields ( up to 87%) and high stereoselectivity under the optimized reaction conditions.

  DOI：

  10.1021/jo0606103

文献信息

• Directing Group Assisted Copper-Catalyzed Chemoselective <i>O</i>-Aroylation of Phenols and Enols Using Alkylbenzenes
  作者：Saroj Kumar Rout、Srimanta Guin、Arghya Banerjee、Nilufa Khatun、Anupal Gogoi、Bhisma K. Patel

  DOI：10.1021/ol401682a

  日期：2013.8.16

  By using alkylbenzenes as aroyl surrogates, copper(II) catalyzed chemoselective O-aroylations of 1,3-dicarbonyl compounds and phenolic -OH ortho to carbonyl (-CHO, -COR) groups have been achieved. A dual mechanism operating in tandem for these transformations has been supported by a crossover experiment.
• MOHRIG, J. R.;DABORA, S. L.;FOSTER, T. F.;SCHULZ, S. C., J. ORG. CHEM., 1984, 49, N 26, 5179-5182
  作者：MOHRIG, J. R.、DABORA, S. L.、FOSTER, T. F.、SCHULZ, S. C.

  DOI：——

  日期：——
• Highly Stereoselective Oxidative Esterification of Aldehydes with β-Dicarbonyl Compounds
  作者：Woo-Jin Yoo、Chao-Jun Li

  DOI：10.1021/jo0606103

  日期：2006.8.1

  Copper-catalyzed oxidative esterification of aldehydes with beta-dicarbonyl compounds was developed using tert-butyl hydroperoxide as an oxidant. In general, the enol esters were synthesized in good yields ( up to 87%) and high stereoselectivity under the optimized reaction conditions.
• Stereospecific synthesis of 2-deuterio-3-hydroxybutanoate esters. Regiochemistry and stereochemistry of homogeneous hydrogenation with Wilkinson's catalyst
  作者：Jerry R. Mohrig、Sandra L. Dabora、Ted F. Foster、Steve C. Schultz

  DOI：10.1021/jo00200a033

  日期：1984.12