3-methylene-5-tridecyltetrahydrofuran-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3-methylene-5-tridecyltetrahydrofuran-2-one
• 英文别名: 3-Methylidene-5-tridecyloxolan-2-one；3-methylidene-5-tridecyloxolan-2-one
• 化学式: C₁₈H₃₂O₂
• 分子量: 280.451
• InChiKey: PLZXNCMTDJZMBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  3-methylene-5-tridecyltetrahydrofuran-2-one 在 rhodium(III) chloride 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以88%的产率得到4-methyl-5-oxo-2-tridecyl-2H-furanone
  参考文献：
  名称：

  Protolichesterinic acid derivatives: α-Methylene-γ-lactones as potent dual activators of PPARγ and Nrf2 transcriptional factors

  摘要：

  PPARγ and Nrf2 are important transcriptional factors involved in many signaling pathways, especially in the anti-infectious response of macrophages. Compounds bearing a Michael acceptor moiety are well known to activate such transcriptional factors, we thus evaluated the potency of α,β-unsaturated lactones synthesized using fluorous phase organic synthesis. Compounds were first screened for their cytotoxicity in order to select lactones for PPARγ and Nrf2 activation evaluation. Among them, two α-methylene-γ-lactones were identified as potent dual activators of PPARγ and Nrf2 in macrophages.

  DOI：

  10.1016/j.bmcl.2014.06.062
• 作为产物：
  描述：

  十四醇 在 pyridinium dichromate 、 bis(benzonitrile)palladium(II) chloride 、 tin(ll) chloride 作用下， 以 N-甲基吡咯烷酮 、 二氯甲烷 、 水 为溶剂， 反应 68.0h， 生成 3-methylene-5-tridecyltetrahydrofuran-2-one
  参考文献：
  名称：

  Protolichesterinic acid derivatives: α-Methylene-γ-lactones as potent dual activators of PPARγ and Nrf2 transcriptional factors

  摘要：

  PPARγ and Nrf2 are important transcriptional factors involved in many signaling pathways, especially in the anti-infectious response of macrophages. Compounds bearing a Michael acceptor moiety are well known to activate such transcriptional factors, we thus evaluated the potency of α,β-unsaturated lactones synthesized using fluorous phase organic synthesis. Compounds were first screened for their cytotoxicity in order to select lactones for PPARγ and Nrf2 activation evaluation. Among them, two α-methylene-γ-lactones were identified as potent dual activators of PPARγ and Nrf2 in macrophages.

  DOI：

  10.1016/j.bmcl.2014.06.062

文献信息

• Protolichesterinic acid derivatives: α-Methylene-γ-lactones as potent dual activators of PPARγ and Nrf2 transcriptional factors
  作者：Anne-Cécile Le Lamer、Hélène Authier、Isabelle Rouaud、Agnès Coste、Joël Boustie、Bernard Pipy、Nicolas Gouault

  DOI：10.1016/j.bmcl.2014.06.062

  日期：2014.8

  PPARγ and Nrf2 are important transcriptional factors involved in many signaling pathways, especially in the anti-infectious response of macrophages. Compounds bearing a Michael acceptor moiety are well known to activate such transcriptional factors, we thus evaluated the potency of α,β-unsaturated lactones synthesized using fluorous phase organic synthesis. Compounds were first screened for their cytotoxicity in order to select lactones for PPARγ and Nrf2 activation evaluation. Among them, two α-methylene-γ-lactones were identified as potent dual activators of PPARγ and Nrf2 in macrophages.