E-1-(4-hydroxy-2,6,6-trimethylcyclohex-2-enyl)-3-phenylprop-2-en-1-one | 219502-69-9

• 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-1-(4-hydroxy-2,6,6-trimethylcyclohex-2-enyl)-3-phenylprop-2-en-1-one
• 英文别名: (E)-1-(4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)-3-phenylprop-2-en-1-one
• CAS: 219502-69-9
• 化学式: C₁₈H₂₂O₂
• 分子量: 270.371
• InChiKey: IODPQJFCSODSRZ-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 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-1-(4-hydroxy-2,6,6-trimethylcyclohex-2-enyl)-3-phenylprop-2-en-1-one 在 jones reagent 作用下， 以 丙酮 为溶剂， 反应 0.25h， 以95%的产率得到E-2,6,6-trimethyl-4-(3-phenylacryloyl)cyclohex-2-enone
  参考文献：
  名称：

  Synthesis of Active Antifeedant CDE Fragments of 11-Ketoepoxyazadiradione Based on an Electrocyclization Reaction Catalyzed by Perchloric Acid

  摘要：

  A synthetic route to mimics of the insect antifeedant epoxyazadiradione containing the CDE molecular fragment with an oxygenated function on ring C has been developed. The key step is based on a 2,6-diene-1,5-dione electrocyclization reaction catalyzed by perchloric acid, The rearrangement of the epoxy alcohol epimers 12 and 19 induced by acids deserves special mention. Several of the compounds obtained show significant antifeedant activity against Spodoptera frugiperda.

  DOI：

  10.1021/jo981456q
• 作为产物：
  描述：

  4-acetyl-3,5,5-trimethylcyclohex-2-enone 在 sodium hydroxide 、 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 9.33h， 生成 E-1-(4-hydroxy-2,6,6-trimethylcyclohex-2-enyl)-3-phenylprop-2-en-1-one
  参考文献：
  名称：

  Synthesis of Active Antifeedant CDE Fragments of 11-Ketoepoxyazadiradione Based on an Electrocyclization Reaction Catalyzed by Perchloric Acid

  摘要：

  A synthetic route to mimics of the insect antifeedant epoxyazadiradione containing the CDE molecular fragment with an oxygenated function on ring C has been developed. The key step is based on a 2,6-diene-1,5-dione electrocyclization reaction catalyzed by perchloric acid, The rearrangement of the epoxy alcohol epimers 12 and 19 induced by acids deserves special mention. Several of the compounds obtained show significant antifeedant activity against Spodoptera frugiperda.

  DOI：

  10.1021/jo981456q

文献信息

• Synthesis of Active Antifeedant CDE Fragments of 11-Ketoepoxyazadiradione Based on an Electrocyclization Reaction Catalyzed by Perchloric Acid
  作者：Alfonso Fernández-Mateos、Eva M. Martín de la Nava、Gustavo Pascual Coca、Rosa Rubio González、Ana I. Ramos Silvo、M. S. J. Simmonds、W. M. Blaney

  DOI：10.1021/jo981456q

  日期：1998.12.1

  A synthetic route to mimics of the insect antifeedant epoxyazadiradione containing the CDE molecular fragment with an oxygenated function on ring C has been developed. The key step is based on a 2,6-diene-1,5-dione electrocyclization reaction catalyzed by perchloric acid, The rearrangement of the epoxy alcohol epimers 12 and 19 induced by acids deserves special mention. Several of the compounds obtained show significant antifeedant activity against Spodoptera frugiperda.