methyl (E)-2-oxo-4-(4-ethoxyphenyl)but-3-enoate | 106381-24-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl (E)-2-oxo-4-(4-ethoxyphenyl)but-3-enoate
• 英文别名: 4t-(4-ethoxy-phenyl)-2-oxo-but-3-enoic acid methyl ester；4t-(4-Aethoxy-phenyl)-2-oxo-but-3-ensaeure-methylester；3-Oxo-1t-(4-aethoxy-phenyl)-buten-(1)-saeure-(4)-methylester
• CAS: 106381-24-2
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: HZVPBSLKRAPQJV-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.84
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (E)-2-oxo-4-(4-ethoxyphenyl)but-3-enoate 在 氯仿 、 溴 作用下， 生成 4-(4-ethoxy-phenyl)-3,4-dibromo-2-oxo-butyric acid methyl ester
  参考文献：
  名称：

  Addition Reactions of alpha-Ketonic Acids. VII

  摘要：

  DOI：

  10.1021/ja01846a055
• 作为产物：
  描述：

  4-乙氧基苯甲醛 在 盐酸 、 甲醇 、 氢氧化钾 作用下， 生成 methyl (E)-2-oxo-4-(4-ethoxyphenyl)but-3-enoate
  参考文献：
  名称：

  Addition Reactions of alpha-Ketonic Acids. VII

  摘要：

  DOI：

  10.1021/ja01846a055

文献信息

• Highly Enantioselective Michael Addition of Cyclic 1,3-Dicarbonyl Compounds to β,γ-Unsaturated α-Keto Esters
  作者：Xing-Kuan Chen、Chang-Wu Zheng、Sheng-Li Zhao、Zhuo Chai、Ying-Quan Yang、Gang Zhao、Wei-Guo Cao

  DOI：10.1002/adsc.201000045

  日期：——

  A highly enantioselective Michael addition of cyclic 1,3‐dicarbonyl compounds to β,γ‐unsaturated α‐keto esters catalyzed by amino acid‐derived thiourea‐tertiary‐amine catalysts is presented. Using 5 mol% of a novel tyrosine‐derived thiourea catalyst, a series of chiral coumarin derivatives were obtained in excellent yields (up to 99%) and with up to 96% ee under very mild conditions within a short

  提出了由氨基酸衍生的硫脲-叔胺催化剂催化的环状1,3-二羰基化合物对β，γ-不饱和α-酮酯的高对映选择性迈克尔加成反应。使用5 mol％的新型酪氨酸衍生的硫脲催化剂，可在极短的反应时间内，在非常温和的条件下，以优异的收率（高达99％）和高达96％ee获得一系列手性香豆素衍生物。
• An unexpected tandem enantioselective Michael addition/oxa-nucleophilic rearrangement reaction of β,γ-unsaturated α-keto esters catalyzed by cinchona alkaloids
  作者：Hai-Feng Wang、Chang-Wu Zheng、Ying-Quan Yang、Zhuo Chai、Gang Zhao

  DOI：10.1016/j.tetasy.2008.11.007

  日期：2008.11

  Cinchona alkaloids were found to catalyze an enantioselective Michael addition/oxa-nucleophilic rearrangement reaction of β,γ-unsaturated α-keto esters 1 and malonates 2. Using the optimum catalyst quinine 4a, a series of the rearranged products 3 were obtained with up to 98% yield and 82% ee under mild reaction conditions.

  发现金鸡纳生物碱催化β，γ-不饱和α-酮酯1和丙二酸酯2的对映选择性迈克尔加成/氧合亲核重排反应。使用最佳催化剂奎宁4a，在温和的反应条件下获得了一系列重排产物3，产率高达98％，ee达到82％。
• Bifunctional cinchona alkaloids-catalyzed asymmetric [4+2] cycloaddition reaction of β,γ-unsaturated α-keto esters with oxazolones
  作者：Yin Ying、Zhuo Chai、Hai-Feng Wang、Peng Li、Chang-Wu Zheng、Gang Zhao、Yue-Peng Cai

  DOI：10.1016/j.tet.2011.03.069

  日期：2011.5

  A highly enantioselective [4+2] cycloaddition reaction of beta,gamma-unsaturated alpha-keto esters with oxazolones was realized with readily available cinchona alkaloids as the catalysts. Using this reaction, a series of highly functionalized delta-lactones with adjacent alpha-quaternary-beta-tertiary stereocenters were obtained in high yields (up to 97%) and with good-to-excellent enantioselectivities (up to 97% ee). (C) 2011 Elsevier Ltd. All rights reserved.