ethyl 2-acetyl-3-phenyl-3-butenoate

• 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: ethyl 2-acetyl-3-phenyl-3-butenoate
• 英文别名: Ethyl 2-acetyl-3-phenylbut-3-enoate；ethyl 2-acetyl-3-phenylbut-3-enoate
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: UMVAFLSSNZKILJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 苯乙炔 在 [ReBr(CO)3(thf)]2 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 以93%的产率得到ethyl 2-acetyl-3-phenyl-3-butenoate
  参考文献：
  名称：

  Manganese-Catalyzed Construction of Tetrasubstituted Benzenes from 1,3-Dicarbonyl Compounds and Terminal Acetylenes

  摘要：

  Treatment of beta-keto esters with terminal acetylenes in the presence of a catalytic amount of a manganese complex, MnBr(CO)(5), and molecular sieves, gave multisubstituted aromatic compounds in good to excellent yields. This reaction employs [2 + 2 + 2] cycloaddition of beta-keto esters and 2 equiv of terminal acetylenes with dehydration. In the case of a 1,3-diketone, the corresponding acetophenone derivative and its deacylated compound can be synthesized selectively.

  DOI：

  10.1021/ol800969h

文献信息

• Rhenium-Catalyzed Insertion of Terminal Acetylenes into a C−H Bond of Active Methylene Compounds
  作者：Yoichiro Kuninobu、Atsushi Kawata、Kazuhiko Takai

  DOI：10.1021/ol0515208

  日期：2005.10.1

  [GRAPHICS]A rhenium complex, [ReBr(CO)(3)(thf)](2), Catalyzed the intermolecular reactions of 1,3-dicarbonyl compounds with terminal acetylenes and gave the corresponding alkenyl derivatives in excellent yields. These reactions could apply to an intramolecular version and gave the corresponding cyclic compounds quantitatively.
• Manganese-Catalyzed Construction of Tetrasubstituted Benzenes from 1,3-Dicarbonyl Compounds and Terminal Acetylenes
  作者：Yoichiro Kuninobu、Mitsumi Nishi、Salprima Yudha S.、Kazuhiko Takai

  DOI：10.1021/ol800969h

  日期：2008.7.17

  Treatment of beta-keto esters with terminal acetylenes in the presence of a catalytic amount of a manganese complex, MnBr(CO)(5), and molecular sieves, gave multisubstituted aromatic compounds in good to excellent yields. This reaction employs [2 + 2 + 2] cycloaddition of beta-keto esters and 2 equiv of terminal acetylenes with dehydration. In the case of a 1,3-diketone, the corresponding acetophenone derivative and its deacylated compound can be synthesized selectively.