(E)-1-(4-methoxyphenyl)-4-methylhexa-1,4,5-trien-3-one | 1126624-06-3

• 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)-1-(4-methoxyphenyl)-4-methylhexa-1,4,5-trien-3-one
• CAS: 1126624-06-3
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: KSNLXZOFMONPSG-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-methoxyphenyl)-4-methylhexa-1,4,5-trien-3-one 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Synthesis of 5-Hydroxycyclopent-2-enones from Allenyl Vinyl Ketones via an Interrupted Nazarov Cyclization

  摘要：

  Treatment of an allenyl vinyl ketone with trifluoroacetic acid leads to Nazarov cyclization, and the intermediate carbocation is trapped efficiently by trifluoroacetate. Hydrolysis of the ester with methanol and basic alumina provides, in good to excellent overall yield, a 5-hydroxycyclopent-2-enone in which the alcohol is predominantly trans to a substituent at C-4.

  DOI：

  10.1021/ol900029d
• 作为产物：
  描述：

  (E)-1-(4-methoxyphenyl)-4-methylhexa-1,4,5-trien-3-ol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以68%的产率得到(E)-1-(4-methoxyphenyl)-4-methylhexa-1,4,5-trien-3-one
  参考文献：
  名称：

  Synthesis of 5-Hydroxycyclopent-2-enones from Allenyl Vinyl Ketones via an Interrupted Nazarov Cyclization

  摘要：

  Treatment of an allenyl vinyl ketone with trifluoroacetic acid leads to Nazarov cyclization, and the intermediate carbocation is trapped efficiently by trifluoroacetate. Hydrolysis of the ester with methanol and basic alumina provides, in good to excellent overall yield, a 5-hydroxycyclopent-2-enone in which the alcohol is predominantly trans to a substituent at C-4.

  DOI：

  10.1021/ol900029d

文献信息

• Synthesis of 5-Hydroxycyclopent-2-enones from Allenyl Vinyl Ketones via an Interrupted Nazarov Cyclization
  作者：Vanessa M. Marx、D. Jean Burnell

  DOI：10.1021/ol900029d

  日期：2009.3.19

  Treatment of an allenyl vinyl ketone with trifluoroacetic acid leads to Nazarov cyclization, and the intermediate carbocation is trapped efficiently by trifluoroacetate. Hydrolysis of the ester with methanol and basic alumina provides, in good to excellent overall yield, a 5-hydroxycyclopent-2-enone in which the alcohol is predominantly trans to a substituent at C-4.