2,4-Dimethyl-5-[2-oxo-2-phenyl-eth-(Z)-ylidene]-cyclopenta-1,3-dienecarboxylic acid ethyl ester | 174415-89-5

• 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: 2,4-Dimethyl-5-[2-oxo-2-phenyl-eth-(Z)-ylidene]-cyclopenta-1,3-dienecarboxylic acid ethyl ester
• 英文别名: ethyl (5Z)-2,4-dimethyl-5-phenacylidenecyclopenta-1,3-diene-1-carboxylate
• CAS: 174415-89-5
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: GDUAFOODHKLSIS-PTNGSMBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,4-Dimethyl-5-[2-oxo-2-phenyl-eth-(Z)-ylidene]-cyclopenta-1,3-dienecarboxylic acid ethyl ester 以 neat (no solvent) 为溶剂， 生成 (3aS,4S,7S,7aS)-3,5,7,7a-Tetramethyl-1,8-bis-[2-oxo-2-phenyl-eth-(Z)-ylidene]-1,3a,7,7a-tetrahydro-4,7-methano-indene-2,4-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  功能化富烯的新一步合成

  摘要：

  功能化的富烯通过烯丙基三苯基膦和 1,2-二酰基乙炔的缩合在单一操作中制备。

  DOI：

  10.1246/cl.1996.71
• 作为产物：
  描述：

  1-phenyl-2-penten-1,4-dione 在 溴 、 碳酸氢钠 、 三乙胺 作用下， 以 四氯化碳 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 14.0h， 生成 2,4-Dimethyl-5-[2-oxo-2-phenyl-eth-(Z)-ylidene]-cyclopenta-1,3-dienecarboxylic acid ethyl ester
  参考文献：
  名称：

  [3 + 2] Annulation of Allylidenetriphenylphosphorane with 1,2-Diacylethylenes and 1,2-Diacylacetylenes:  A One-Step Synthesis of Tri- and Tetrasubstituted Cyclopentadienes and Fulvenes

  摘要：

  Allylidenetriphenylphosphoranes underwent [3 + 2] annulation with 1,2-diacylethylenes at room temperature to give cyclopentadienes 11-17 having various substituents except for (Z)-3-acetylacrolein (18) which gave cyclohexadiene 19 derived from [3 + 3] annulation as the sole annulation product. The resulting cyclopentadienes were mixtures of the corresponding double-bond isomers which arose through an equilibrium process from the initially formed 1,3-dienes a under the weakly basic reaction conditions. Similar reactions of the phosphoranes with 1,2-diacylacetylenes afforded substituted fulvenes 24, 25, and 28 directly without the attendant formation of the corresponding benzene derivatives which come from another possible [3 + 3] annulation. The observed high level of the preference for the [3 + 2] annulation is discussed on the basis of the semiempirical PM3 MO calculations. The calculations suggested that the course of the annulation may be kinetically controlled at the oxaphosphetane-forming step of the intramolecular Wittig reaction.

  DOI：

  10.1021/jo970594x