(E)-ethyl 4-(3-methylphenyl)-4-hydroxybut-2-enoate | 1417403-48-5

• 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: (E)-ethyl 4-(3-methylphenyl)-4-hydroxybut-2-enoate
• 英文别名: ethyl (E)-4-hydroxy-4-(3-methylphenyl)but-2-enoate
• CAS: 1417403-48-5
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: DYIAFPCTEHYGPJ-BQYQJAHWSA-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：
  0.31
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-methylbenzensulfonyl)-4-phenyl-1H-1,2,3-triazole 、 (E)-ethyl 4-(3-methylphenyl)-4-hydroxybut-2-enoate 在 rhodium(II) pivalate 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以80%的产率得到ethyl (3E)-4-(3-methylphenyl)but-2-(1-{[(4-methylphenyl)sulfonyl]amino}-2-oxo-2-phenylethyl)-3-enoate
  参考文献：
  名称：

  Cu^I/Rh^II-Catalyzed Tandem Convergent Multicomponent Reaction for the Regio- and Stereocontrolled Synthesis of γ-Oxo-β-amino Esters

  摘要：

  The first example of a highly regio- and stereo-selective catalytic method for the three-component one-pot synthesis of highly functionalized alpha-vinylated gamma-oxo-beta-amino esters is disclosed. In this catalytic triad, the Cu-I-catalyst selectively catalyzes the, cycloaddition of the 1-alkyne and sulfonyl azide first resulting in the corresponding 1-sulfonyl-1,2,3-triazole. An a-imino Rh-II-carbene is generated from an open-chain alpha-imino diazo of the triazole, and this species reacts with gamma-hydroxy alpha,beta-unsaturated esters to form allylic (Z)-amino vinyl ethers. Rapid deconjugative [3,3]-sigmatropic rearrangement affords the alpha-vinyl gamma-oxo-beta-amino esters in high yields with high levels of diastereoselectivity.

  DOI：

  10.1021/acs.orglett.5b01587
• 作为产物：
  描述：

  3-甲基苯甲醛 、 丙烯酸乙酯 在 三(4-甲氧苯基)膦 作用下， 以 氯仿 为溶剂， 反应 24.0h， 生成 (E)-ethyl 4-(3-methylphenyl)-4-hydroxybut-2-enoate 、 4-(3-甲基苯基)-4-氧代丁酸乙酯
  参考文献：
  名称：

  三(4-甲氧基苯基)膦催化的CC键形成反应：芳香醛和丙烯酸乙酯的相互加成

  摘要：

  摘要 以三(4-甲氧基苯基)膦为催化剂，开发了芳香醛与丙烯酸乙酯的高效分子间互加成反应。该反应对应于1,4-二羰基化合物和烯丙醇片段的构建，这也为CC键的形成提供了新的途径。图形概要

  DOI：

  10.1080/00397911.2011.610551

文献信息

• Tris(4-methoxylphenyl)phosphine-Catalyzed C-C Bond Formation Reaction: Mutual Addition of Aromatic Aldehydes and Ethyl Acrylate
  作者：Jun-Jiang Teng、Yan-Hui Qiao、Qing Zhang、Chun-Hai Li、Min Huang

  DOI：10.1080/00397911.2011.610551

  日期：2013.2.1

  Abstract A highly efficient intermolecular mutual addition of aromatic aldehydes with ethyl acrylate was developed by using tris(4-methoxylphenyl)phosphine as the catalyst. The reaction corresponds to the construction of 1,4-dicarbonyl compound and allylic alcohol fragments, which also provides a new way to form C-C bond. GRAPHICAL ABSTRACT

  摘要 以三(4-甲氧基苯基)膦为催化剂，开发了芳香醛与丙烯酸乙酯的高效分子间互加成反应。该反应对应于1,4-二羰基化合物和烯丙醇片段的构建，这也为CC键的形成提供了新的途径。图形概要
• Cu^I/Rh^II-Catalyzed Tandem Convergent Multicomponent Reaction for the Regio- and Stereocontrolled Synthesis of γ-Oxo-β-amino Esters
  作者：Da Jung Jung、Hyun Ji Jeon、Joo Hyun Lee、Sang-gi Lee

  DOI：10.1021/acs.orglett.5b01587

  日期：2015.7.17

  The first example of a highly regio- and stereo-selective catalytic method for the three-component one-pot synthesis of highly functionalized alpha-vinylated gamma-oxo-beta-amino esters is disclosed. In this catalytic triad, the Cu-I-catalyst selectively catalyzes the, cycloaddition of the 1-alkyne and sulfonyl azide first resulting in the corresponding 1-sulfonyl-1,2,3-triazole. An a-imino Rh-II-carbene is generated from an open-chain alpha-imino diazo of the triazole, and this species reacts with gamma-hydroxy alpha,beta-unsaturated esters to form allylic (Z)-amino vinyl ethers. Rapid deconjugative [3,3]-sigmatropic rearrangement affords the alpha-vinyl gamma-oxo-beta-amino esters in high yields with high levels of diastereoselectivity.