(E)-methyl 3-(1-naphthyl)-2,5-hexadienoate | 1240327-44-9

• 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)-methyl 3-(1-naphthyl)-2,5-hexadienoate
• 英文别名: methyl (2E)-3-naphthalen-1-ylhexa-2,5-dienoate
• CAS: 1240327-44-9
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: QUBXAEBTDAJXLC-WYMLVPIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  甲醇 、 一氧化碳 、 (E)-1-bromo-2-(1-naphthyl)-1,4-pentadiene 在 bis-triphenylphosphine-palladium(II) chloride 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 100.0 ℃ 、1.01 MPa 条件下， 反应 3.5h， 以80%的产率得到(E)-methyl 3-(1-naphthyl)-2,5-hexadienoate
  参考文献：
  名称：

  Regioselective Synthesis of 1-Bromo-1,4-dienes by Free-Radical-Mediated Bromoallylation of Activated Acetylenes

  摘要：

  The free-radical-mediated bromoallylation of acetylenes proceeded efficiently in the presence of V-65 (2,2-azobis(2,4-dimethylvaleronitrile)) as the radical initiator. The regioselective reaction, which yields 1-bromo-2-substituted 1,4-dienes, is complementary to the Pd-catalyzed bromoallylation reaction previously reported by Kaneda. The products of the free-radical-mediated bromoallylation of acetylenes could be converted into a variety of substituted dienes by subsequent Pd-catalyzed reactions.

  DOI：

  10.1021/ol1016096

文献信息

• Regioselective Synthesis of 1-Bromo-1,4-dienes by Free-Radical-Mediated Bromoallylation of Activated Acetylenes
  作者：Takashi Kippo、Takahide Fukuyama、Ilhyong Ryu

  DOI：10.1021/ol1016096

  日期：2010.9.17

  The free-radical-mediated bromoallylation of acetylenes proceeded efficiently in the presence of V-65 (2,2-azobis(2,4-dimethylvaleronitrile)) as the radical initiator. The regioselective reaction, which yields 1-bromo-2-substituted 1,4-dienes, is complementary to the Pd-catalyzed bromoallylation reaction previously reported by Kaneda. The products of the free-radical-mediated bromoallylation of acetylenes could be converted into a variety of substituted dienes by subsequent Pd-catalyzed reactions.