4-(4-Chlorophenyl)-4-oxobut-2-enoic acid methyl ester | 99822-65-8

• 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: 4-(4-Chlorophenyl)-4-oxobut-2-enoic acid methyl ester
• 英文别名: methyl 4-(4-chlorophenyl)-4-oxobut-2-enoate
• CAS: 99822-65-8
• 化学式: C₁₁H₉ClO₃
• 分子量: 224.644
• InChiKey: WKRNZICCAQRRLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-Chlorophenyl)-4-oxobut-2-enoic acid methyl ester 在 盐酸 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 72.0h， 生成 methyl 4-(4-chlorophenyl)-2-(2,3-dioxoindolin-1-yl)-4-oxobutanoate
  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
• 作为产物：
  描述：

  3-(4-氯苯甲酰)丙酸 在 硫酸 、 溴 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 0.5h， 生成 4-(4-Chlorophenyl)-4-oxobut-2-enoic acid methyl ester
  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

• Phosphine-Catalyzed Diastereo- and Enantioselective Michael Addition of β-Carbonyl Esters to β-Trifluoromethyl and β-Ester Enones: Enhanced Reactivity by Inorganic Base
  作者：Ben Huang、Cao Li、Huamin Wang、Caihui Wang、Lu Liu、Junliang Zhang

  DOI：10.1021/acs.orglett.7b02365

  日期：2017.10.6

  A novel chiral biamide–phosphine multifunctional catalyst has been developed that mediates the asymmetric intermolecular Michael addition of β-carbonyl esters to β-trifluoromethyl enones and 3-aroyl acrylates in the presence of competing methyl acrylate and the inorganic base. This method provides a facile access to structurally diverse trifluoromethyl and quaternary stereogenic centers with excellent

  已经开发出一种新型的手性联酰胺-膦多功能催化剂，该催化剂在竞争性丙烯酸甲酯和无机碱的存在下，将β-羰基酯的不对称分子间迈克尔加成反应成β-三氟甲基烯酮和3-芳基丙烯酸酯。此方法可轻松访问结构多样的三氟甲基和季立体异构中心，具有出色的对映选择性（高达99％ee）和良好的非对映选择性（高达13：1 dr）。无机碱（K 3 PO 4）的添加不会引起背景外消旋反应，并且通过用作助催化剂来增强反应性。
• 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。