methyl 4-(4-methoxyphenyl)-4-oxobut-2-enoate | 17615-10-0

• 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 4-(4-methoxyphenyl)-4-oxobut-2-enoate
• 英文别名: 4-(4-methoxy-phenyl)-4-oxo-crotonic acid methyl ester；4-(4-Methoxy-phenyl)-4-oxo-crotonsaeure-methylester；β-Anisoyl-acrylsaeure-methylester
• CAS: 17615-10-0
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: PZFZTRCQJQJNNP-UHFFFAOYSA-N

物化性质

• 熔点：
  72 °C
• 沸点：
  344.7±42.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 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 4-(4-methoxyphenyl)-4-oxobut-2-enoate 在 盐酸 作用下， 生成 2-hydroxy-4-(4-methoxy-phenyl)-4-oxo-butyric acid
  参考文献：
  名称：

  Rice, Journal of the American Chemical Society, 1924, vol. 46, p. 218,219

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(4-甲氧基苯甲酰基)丙酸 在 硫酸 、 溴 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 0.5h， 生成 methyl 4-(4-methoxyphenyl)-4-oxobut-2-enoate
  参考文献：
  名称：

  Remote Activation of the Nucleophilicity of Isatin

  摘要：

  The concept of the remote activation of reactivity was first applied in asymmetric organocatalysis. An isatin 3-phenylimine derivative acts as a donor in the thiourea catalyzed asymmetric addition to unsaturated 1,4-ketoesters, affording aza-Michael adducts in high enantiomeric purity and yield.

  DOI：

  10.1021/ol500421k

文献信息

• Chiral N-heterocyclic carbene-catalyzed generation of ester enolate equivalents from α,β-unsaturated aldehydes for enantioselective Diels–Alder reactions
  作者：Juthanat Kaeobamrung、Marisa C. Kozlowski、Jeffrey W. Bode

  DOI：10.1073/pnas.1007469107

  日期：2010.11.30

  The catalytic generation of chiral ester enolate equivalents from alpha,beta-unsaturated aldehydes with chiral N-hetereocyclic carbene catalysts makes possible highly enantioselective hetero-Diels-Alder reactions. The reactions proceed under simple, mild conditions with both aliphatic and aromatic substituted enals as substrates. Previous attempts to employ these starting materials as enolate precursors

  使用手性 N-杂环卡宾催化剂从 α,β-不饱和醛催化生成手性酯烯醇化物等价物使得高度对映选择性的杂狄尔斯-阿尔德反应成为可能。反应在简单、温和的条件下进行，脂肪族和芳香族取代的烯醛作为底物。先前尝试将这些起始材料用作烯醇化物前体，通过催化产生的均烯醇化物等价物得到结构不同的产物。烯醇生成成功的关键是用于生成活性 N-杂环卡宾催化剂的催化碱的强度。为了补充这些研究，我们使用计算方法研究了烯醇结构，发现它更喜欢垂直于三唑核的构象。
• Synthesis of 3-Benzoyl Acrylates/Acrylamides via Dehydrogenation of 3-Benzoyl Propionates/Propionamides Using IBX/p-TsOH
  作者：Ziyuan Li、Yiyun Wang、Changhua Tang、Jinyi Xu、Xiaoming Wu、Hequan Yao

  DOI：10.1002/cjoc.201090225

  日期：——

  Dehydrogenation by IBX/p‐TsOH is applied to the conversion of 3‐benzoyl propionates/propionamides to 3‐benzoyl acrylates/acrylamides in moderate to excellent yields. The reaction time for the dehydrogenation of 3‐benzoyl propionamides was remarkably shorter than that for the dehydrogenation of esters.

  IBX / p- TsOH进行的脱氢用于将3-苯甲酰基丙酸酯/丙酰胺以中等至极好的收率转化为3-苯甲酰基丙烯酸酯/丙烯酰胺。3-苯甲酰基丙酰胺脱氢的反应时间明显短于酯脱氢的反应时间。
• Diversity-Oriented Three-Component Reactions of Diazo Compounds with Anilines and 4-Oxo-Enoates
  作者：Changcheng Jing、Dong Xing、Yu Qian、Taoda Shi、Yun Zhao、Wenhao Hu

  DOI：10.1002/anie.201303987

  日期：2013.8.26

  Choosing a path: The title reaction can proceed through two different reaction pathways, and is controlled by the addition sequence of the substrates. Divergent polyfunctional products, pyrrolidines or linear α‐amino ester derivatives, are obtained in good yields and high diastereoselectivities.

  选择途径：标题反应可以通过两种不同的反应途径进行，并受底物的添加顺序控制。以高收率和高非对映选择性获得了多官能产品，吡咯烷或线性α-氨基酯衍生物。
• Trapping of Oxonium Ylides with Michael Acceptors: Highly Diastereoselective Three-Component Reactions of Diazo Compounds with Alcohols and Benzylidene Meldrum’s Acids/4-Oxo-enoates
  作者：Liqing Jiang、Wenhao Hu、Xingchun Han、Minghua Gan、Huang Qiu、Jingjing Ji、Xia Zhang

  DOI：10.1055/s-0030-1260824

  日期：2011.7

  number of Michael acceptors via a 1,4-addition fashion has been investigated. Benzylidene Meldrum's acids and 4-oxo-enoates have been found to be matched components as suitable Michael acceptors for the transformation. Thus, Rh 2 (OAc) 4 -catalyzed three-component reactions of diazo compounds, alcohols, and benzylidene Meldrum's acids/4-oxo-enoates gave corresponding α-hydroxyesters in good yield with

  已经研究了通过 1,4-加成方式用许多迈克尔受体捕获氧鎓叶立德。已发现亚苄基 Meldrum 的酸和 4-氧代-烯酸酯是匹配的组分，可作为转化的合适迈克尔受体。因此，Rh 2 (OAc) 4 催化重氮化合物、醇和亚苄基 Meldrum 酸/4-氧代烯酸酯的三组分反应以良好的收率和高至极好的非对映选择性得到相应的 α-羟基酯。通过简单的程序将加成产物转化为 γ-丁内酯，证明了这种有效方法的合成效用。
• Highly diastereo- and enantioselective C2 addition of 5<i>H</i>-oxazol-4-ones to γ-keto-α,β-unsaturated esters
  作者：Li Lin、Mei Wang、Jiawei Zhou、Fei Li、Huiyun Liu

  DOI：10.1039/d3cc00554b

  日期：——

  The novel direct C2-addition of azlactones to γ-keto-α,β-unsaturated esters was achieved with excellent stereoselectivities, and revealed an unusual π–π interaction effect between the substrate and catalyst.

  使用优异的立体选择性，成功地实现了氮杂环酮直接对γ-酮基-α，β-不饱和酯的C2加成，同时揭示了底物和催化剂之间的不寻常π-π相互作用效应。