methyl β-(p-toluoyl)acrylate | 52348-27-3

• 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 β-(p-toluoyl)acrylate
• 英文别名: Methyl 4-(4-methylphenyl)-4-oxobut-2-enoate
• CAS: 52348-27-3
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: SZDKHFAFBYVCTN-UHFFFAOYSA-N

物化性质

• 熔点：
  45.4-46 °C
• 沸点：
  240-245 °C(Press: 115 Torr)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  methyl β-(p-toluoyl)acrylate 在 N-[3,5-二(三氟甲基)苯基]-N-[(9R)-6-甲氧基-9-二奎宁基]硫脲 、 盐酸 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 216.0h， 生成 (S)-methyl 2-(2,3-dioxoindolin-1-yl)-4-oxo-4-p-tolylbutanoate
  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-甲基苯甲酰)丙酸 在 硫酸 、 溴 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 0.5h， 生成 methyl β-(p-toluoyl)acrylate
  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

• Systematic investigations on the reduction of 4-aryl-4-oxoesters to 1-aryl-1,4-butanediols with methanolic sodium borohydride
  作者：Subrata Kumar Chaudhuri、Manabendra Saha、Amit Saha、Sanjay Bhar

  DOI：10.3762/bjoc.6.94

  日期：——

  4-Aryl-4-oxoesters undergo facile reduction of both the keto and the ester groups with methanolic NaBH₄ at room temperature to yield the corresponding 1-aryl-1,4-butanediols whereas 4-alkyl-4-oxoesters furnish the corresponding 1,4-butanolides via selective reduction of the keto moiety. Results of a detailed and systematic investigation of the reaction are described.

  4-芳基-4-氧代酯在室温下与甲醇中的NaBH₄发生反应，可以轻易地同时还原其酮基和酯基，生成相应的1-芳基-1,4-丁二醇，而4-烷基-4-氧代酯则通过选择性地还原酮基部分，得到相应的1,4-丁内酯。本文详细描述了这一反应的全面和系统性的研究结果。

• 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。
• 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。
• N-heterocyclic carbene-catalyzed cyclocondensation of 2-aryl carboxylic acids and enones: highly enantioselective synthesis of δ-lactones
  作者：Jin-Tang Cheng、Xiang-Yu Chen、Song Ye

  DOI：10.1039/c4ob02330g

  日期：——

  The enantioselective N-heterocyclic carbene-catalyzed [4 + 2] cyclocondensation of 2-aryl carboxylic acids and enones was developed, affording the corresponding chiral δ-lactones in good yields with good diastereo- and high enantioselectivities.

  开发了对映选择性的N-杂环卡宾催化的2-芳基羧酸和烯酮的[4 + 2]环缩合反应，可提供高收率的非对映异构和高对映选择性的相应手性δ-内酯。
• Organocatalytic Enantioselective Direct Vinylogous Michael Addition of γ-Substituted Butenolides to 3-Aroyl Acrylates and 1,2-Diaroylethylenes
  作者：Utpal Das、Yi-Ru Chen、Yi-Ling Tsai、Wenwei Lin

  DOI：10.1002/chem.201301332

  日期：2013.6.10

  Adding value: The direct vinylogous Michael addition of γ‐substituted butenolides with a series of 3‐aroyl acrylates and 1,2‐diaroylethylenes has been demonstrated. This organocatalytic method delivers highly enantio‐ and diastereomerically pure γ,γ‐disubstituted butenolides with adjacent quaternary and tertiary stereocenters (see scheme).

  增加值：已证明，γ-取代的丁烯内酯与一系列的3-芳酰基丙烯酸酯和1,2-二芳基乙烯直接乙烯基共价迈克尔加成。这种有机催化方法可提供高度对映体和非对映体纯的γ，γ-二取代丁烯化物，并带有相邻的季和叔立体中心（请参见方案）。