4-(4-Prop-2-enoxyphenyl)but-3-en-2-one | 351335-70-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(4-Prop-2-enoxyphenyl)but-3-en-2-one
• CAS: 351335-70-1
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: LQRQXLFRTJZPCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  4-(4-Prop-2-enoxyphenyl)but-3-en-2-one 在 六氟异丙醇 、 三苯基膦氢溴酸盐 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 6.0h， 生成 S-methyl 6-(4-(allyloxy)phenyl)-3-methyl-2-oxabicyclo[3.1.0]hex-3-ene-5-carbothioate
  参考文献：
  名称：

  富电子的二烯酮在可见光和不可见光下的溶剂依赖性发散反应性：获得环丙烷化的呋喃和丁烯内酯

  摘要：

  在环境条件下，使用六氟异丙醇（HFIP）作为添加剂，可在异丙醇溶剂中对富电子二烯酮进行可见光激发，从而促进分子内自由基级联环化，生成环丙烷化呋喃。空气中的分子双氧在该反应中充当氧化还原催化剂，该反应被提议通过由光瞬变二烯酮到氧的单电子转移（SET）产生的自由基阳离子中间体进行。通过将溶剂从异丙醇更改为HFIP，通过涉及E → Z的离子级联环化，可独家形成取代的丁烯内酯异构化/内酯化/硫醇盐加成。假设HFIP充当介质，氢键供体催化剂以及路易斯酸的替代物。即使在不存在光的情况下也可以进行该反应，并且不需要催化剂或试剂。

  DOI：

  10.1002/adsc.201901273
• 作为产物：
  描述：

  对羟基苯甲醛 在 potassium carbonate 、 sodium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 4.0h， 生成 4-(4-Prop-2-enoxyphenyl)but-3-en-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of allylated and prenylated mono-carbonyl analogs of curcumin as anti-inflammatory agents

  摘要：

  Curcumin has been shown to possess anti-inflammatory activities but has been limited for its low stability and poor bioavailability. We have previously reported four series of 5-carbon linker-containing mono-carbonyl analogs of curcumin (MACs). In continuation of our ongoing research, we designed and synthesized 33 novel allylated or prenylated MACs here, and evaluated their anti-inflammatory effects in RAW 264.7 macrophages. A majority of them effectively inhibited the LPS-induced expression of TNF-alpha and IL-6, especially IL-6. The preliminary SAR and quantitative SAR analysis were conducted. Compound 14q is the most potent analog among them, and exhibits significant protection against LPS-induced death in septic mice. Together, these data present a series of new analogs of curcumin as promising anti-inflammatory agents. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.061

文献信息

• 一类含烯丙基的单羰基姜黄素类似物在制备抗 炎药物中的应用
  申请人：温州医科大学

  公开号：CN103524318B

  公开（公告）日：2016-04-13

  本发明提供了具有抗炎作用的含烯丙基的单羰基姜黄素类似物。另外，本发明还提供了这些化合物的药物组合物以及抗炎用途等。
• Synthesis and biological evaluation of allylated and prenylated mono-carbonyl analogs of curcumin as anti-inflammatory agents
  作者：Zhiguo Liu、Longguang Tang、Peng Zou、Yali Zhang、Zhe Wang、Qilu Fang、Lili Jiang、Gaozhi Chen、Zheng Xu、Huajie Zhang、Guang Liang

  DOI：10.1016/j.ejmech.2013.10.061

  日期：2014.3

  Curcumin has been shown to possess anti-inflammatory activities but has been limited for its low stability and poor bioavailability. We have previously reported four series of 5-carbon linker-containing mono-carbonyl analogs of curcumin (MACs). In continuation of our ongoing research, we designed and synthesized 33 novel allylated or prenylated MACs here, and evaluated their anti-inflammatory effects in RAW 264.7 macrophages. A majority of them effectively inhibited the LPS-induced expression of TNF-alpha and IL-6, especially IL-6. The preliminary SAR and quantitative SAR analysis were conducted. Compound 14q is the most potent analog among them, and exhibits significant protection against LPS-induced death in septic mice. Together, these data present a series of new analogs of curcumin as promising anti-inflammatory agents. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Solvent Dependent Divergent Reactivity of Electron‐Rich Dienones with and without Visible Light: Access to Cyclopropanated Furans and Butenolides
  作者：Jayanta Saha、Indrajit Das

  DOI：10.1002/adsc.201901273

  日期：2020.2.6

  hexafluoroisopropanol (HFIP) as an additive promotes intramolecular radical cascade cyclization to afford cyclopropanated furans. Molecular dioxygen in the air serves as a redox catalyst in this reaction which is proposed to proceed through a radical cation intermediate generated by single‐electron transfer (SET) from a phototransient dienone to oxygen. By changing the solvent from isopropanol to HFIP

  在环境条件下，使用六氟异丙醇（HFIP）作为添加剂，可在异丙醇溶剂中对富电子二烯酮进行可见光激发，从而促进分子内自由基级联环化，生成环丙烷化呋喃。空气中的分子双氧在该反应中充当氧化还原催化剂，该反应被提议通过由光瞬变二烯酮到氧的单电子转移（SET）产生的自由基阳离子中间体进行。通过将溶剂从异丙醇更改为HFIP，通过涉及E → Z的离子级联环化，可独家形成取代的丁烯内酯异构化/内酯化/硫醇盐加成。假设HFIP充当介质，氢键供体催化剂以及路易斯酸的替代物。即使在不存在光的情况下也可以进行该反应，并且不需要催化剂或试剂。