(E)-3-heptylidene-5-methyl-6-oxo-2-phenylcyclohex-1-enecarboxylic acid ethyl ester

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-heptylidene-5-methyl-6-oxo-2-phenylcyclohex-1-enecarboxylic acid ethyl ester
• 英文别名: ethyl (3E)-3-heptylidene-5-methyl-6-oxo-2-phenylcyclohexene-1-carboxylate
• 化学式: C₂₃H₃₀O₃
• 分子量: 354.489
• InChiKey: BARXWIYNMWETFB-XDJHFCHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 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：

  苯丙炔酸乙酯 、 2-甲基十一碳-4-炔醛 在 [Rh(dppe)]BF₄ 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以67%的产率得到(E)-6-heptylidene-4-methyl-3-oxo-2-phenylcyclohex-1-enecarboxylic acid ethyl ester
  参考文献：
  名称：

  Rhodium-Catalyzed Synthesis of Cyclohexenones via a Novel [4 + 2] Annulation

  摘要：

  [GRAPHICS]In the presence of a rhodium catalyst, 4-alkynals react with alkynes to furnish cyclohexenones, presumably via metalacycle 1; as far as we are aware, this is the first example of the generation of this class of compounds through such a transformation. In view of the easy accessibility of 4-alkynals (alkynylmetal + alpha,beta-unsaturated aldehyde) and alkynes, this [4 + 2] cyclization constitutes an interesting new approach to functionalized cyclohexenones.

  DOI：

  10.1021/ol017308v

文献信息

• Rhodium-Catalyzed Synthesis of Cyclohexenones via a Novel [4 + 2] Annulation
  作者：Ken Tanaka、Gregory C. Fu

  DOI：10.1021/ol017308v

  日期：2002.3.1

  [GRAPHICS]In the presence of a rhodium catalyst, 4-alkynals react with alkynes to furnish cyclohexenones, presumably via metalacycle 1; as far as we are aware, this is the first example of the generation of this class of compounds through such a transformation. In view of the easy accessibility of 4-alkynals (alkynylmetal + alpha,beta-unsaturated aldehyde) and alkynes, this [4 + 2] cyclization constitutes an interesting new approach to functionalized cyclohexenones.