(E)-6-hydroxy-8-phenyl-2-octen-4-one | 651738-95-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-6-hydroxy-8-phenyl-2-octen-4-one
• 英文别名: (E,6S)-6-hydroxy-8-phenyloct-2-en-4-one
• CAS: 651738-95-3
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: HISDXRDPIJUHGZ-XCVZWFEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-6-hydroxy-8-phenyl-2-octen-4-one 在 palladium dichloride disodium hydrogenphosphate 、 氧气 、 copper(l) chloride 作用下， 以 乙二醇二甲醚 为溶剂， 50.0 ℃ 、101.32 kPa 条件下， 反应 20.0h， 以61%的产率得到6-methyl-2-phenylethyl-2,3-dihydro-4H-pyran-4-one
  参考文献：
  名称：

  Oxidative Cyclization of β-Hydroxyenones with Palladium(II):  A Novel Entry to 2,3-Dihydro-4H-pyran-4-ones

  摘要：

  A palladium(II)-mediated oxidative cyclization was found to be effective for the preparation of structurally diverse 2,3-dihydro-4H-pyran-4-ones from the corresponding beta-hydroxyenones. Attractive features of this transformation include the ready availability of the starting enones, the regiocontrol, and the easy access of enantiopure 2,3-dihydro-4H-pyran-4-one from the corresponding enantiopure enone.

  DOI：

  10.1021/ol0361296
• 作为产物：
  描述：

  3-氧代-5-苯基-戊酸乙酯 在 baker's yeast 、 三甲基铝 作用下， 以 四氢呋喃 为溶剂， 生成 (E)-6-hydroxy-8-phenyl-2-octen-4-one
  参考文献：
  名称：

  Oxidative Cyclization of β-Hydroxyenones with Palladium(II):  A Novel Entry to 2,3-Dihydro-4H-pyran-4-ones

  摘要：

  A palladium(II)-mediated oxidative cyclization was found to be effective for the preparation of structurally diverse 2,3-dihydro-4H-pyran-4-ones from the corresponding beta-hydroxyenones. Attractive features of this transformation include the ready availability of the starting enones, the regiocontrol, and the easy access of enantiopure 2,3-dihydro-4H-pyran-4-one from the corresponding enantiopure enone.

  DOI：

  10.1021/ol0361296

文献信息

• Oxidative Cyclization of β-Hydroxyenones with Palladium(II):  A Novel Entry to 2,3-Dihydro-4<i>H</i>-pyran-4-ones
  作者：Maud Reiter、Sandrine Ropp、Véronique Gouverneur

  DOI：10.1021/ol0361296

  日期：2004.1.1

  A palladium(II)-mediated oxidative cyclization was found to be effective for the preparation of structurally diverse 2,3-dihydro-4H-pyran-4-ones from the corresponding beta-hydroxyenones. Attractive features of this transformation include the ready availability of the starting enones, the regiocontrol, and the easy access of enantiopure 2,3-dihydro-4H-pyran-4-one from the corresponding enantiopure enone.