(E)-3,5,5-trimethyl-4-(3-(thiophen-3-yl)prop-2-enoyl)cyclohex-2-enone | 1248336-57-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-3,5,5-trimethyl-4-(3-(thiophen-3-yl)prop-2-enoyl)cyclohex-2-enone
• CAS: 1248336-57-3
• 化学式: C₁₆H₁₈O₂S
• 分子量: 274.384
• InChiKey: MGYDGZCQNVLTKN-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-3,5,5-trimethyl-4-(3-(thiophen-3-yl)prop-2-enoyl)cyclohex-2-enone 、 乙酸酐 在 N,N-二甲基丙烯基脲 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 1.25h， 以70%的产率得到(E)-3,5,5-trimethyl-4-(3-(thiophen-3-yl)prop-2-enoyl)cyclohexa-1,3-dienyl ethanoate
  参考文献：
  名称：

  Synthesis of limonoid CDE fragments related to limonin and nimbinim

  摘要：

  A practical, brief and selective synthesis of limonoid CDE fragments from a readily available starting diketone is described. The key step is a cationic electrocyclization promoted by strong acids. In general the methodology has been demonstrated for compounds with sensitive furane and thiophene substituents to obtain diverse substituted indenones. Several of the compounds obtained show significant antifeedant activity against Spodoptera littoralis. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.020
• 作为产物：
  描述：

  (E)-1-(4-hydroxy-2,6,6-trimethylcyclohex-2-enyl)-3-(thiophen-3-yl)prop-2-en-1-one 在 Jones reagent 作用下， 以 丙酮 为溶剂， 以88%的产率得到(E)-3,5,5-trimethyl-4-(3-(thiophen-3-yl)prop-2-enoyl)cyclohex-2-enone
  参考文献：
  名称：

  Synthesis of limonoid CDE fragments related to limonin and nimbinim

  摘要：

  A practical, brief and selective synthesis of limonoid CDE fragments from a readily available starting diketone is described. The key step is a cationic electrocyclization promoted by strong acids. In general the methodology has been demonstrated for compounds with sensitive furane and thiophene substituents to obtain diverse substituted indenones. Several of the compounds obtained show significant antifeedant activity against Spodoptera littoralis. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.020