4-(4-Butoxyphenyl)but-3-en-2-one | 37080-14-1

• 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-Butoxyphenyl)but-3-en-2-one
• CAS: 37080-14-1
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: VPZHZTBKGWXHFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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-Butoxyphenyl)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 为溶剂， 反应 9.0h， 生成 (E)-3-(4-butoxystyryl)-5-methyl-5-(methylthio)furan-2(5H)-one
  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：

  丙酮 、 4-丁氧基苯甲醛 在 sodium hydroxide 作用下， 生成 4-(4-Butoxyphenyl)but-3-en-2-one
  参考文献：
  名称：

  Synthesis and biological activity of novel tiliroside derivants

  摘要：

  A series of new tiliroside derivatives were synthesized and characterized by analytical H-1 NMR, C-13 NMR and mass spectrometry. All of the compounds were evaluated for anti-diabetic properties in vitro using HepG2 cells. Compounds 3c, 3d, and 3i-l caused significant enhancements in glucose consumption by insulin-resistant HepG2 cells compared with control cells and cells that were exposed to metformin (an anti-diabetic drug). Moreover, compound 3l significantly activated adenosine 5'-monophosphate-activated protein kinase activity and reduced acetyl-CoA carboxylase activity. Thus, the tiliroside derivative 3l offers potential to be developed as a new approach for treating type II diabetes. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.059

文献信息

• Reaction of CH-acids with Michael acceptors in the presence of potassium carbonate. Syntheses of 6-acetyl- and 3,5-dialkylcyclohex-2-enones
  作者：D. S. Khachatryan、A. A. Vardapetyan、N. M. Morlyan、A. L. Razinov、K. R. Matevosyan

  DOI：10.1007/s11172-015-0873-y

  日期：2015.2

  The reaction of acetylacetone with α,β-enones in the presence of potassium carbonate affords 6-acetylcyclohex-2-enones. The assembly of two acetoacetate and one alkanal molecules gives 3,5-dialkylcyclohex-2-enones. Facile one-pot procedures for these reactions were developed.

  在碳酸钾存在下，乙酰丙酮与 α、β-烯酮反应生成 6-乙酰基环己-2-烯酮。将两个乙酰乙酸酯分子和一个烷烃分子组装在一起可得到 3,5-二烷基环己-2-烯酮。为这些反应开发了简便的一锅反应程序。
• Synthesis and biological activity of novel tiliroside derivants
  作者：Nan Qin、Chun-Bao Li、Mei-Na Jin、Li-Huan Shi、Hong-Quan Duan、Wen-Yan Niu

  DOI：10.1016/j.ejmech.2011.07.059

  日期：2011.10

  A series of new tiliroside derivatives were synthesized and characterized by analytical H-1 NMR, C-13 NMR and mass spectrometry. All of the compounds were evaluated for anti-diabetic properties in vitro using HepG2 cells. Compounds 3c, 3d, and 3i-l caused significant enhancements in glucose consumption by insulin-resistant HepG2 cells compared with control cells and cells that were exposed to metformin (an anti-diabetic drug). Moreover, compound 3l significantly activated adenosine 5'-monophosphate-activated protein kinase activity and reduced acetyl-CoA carboxylase activity. Thus, the tiliroside derivative 3l offers potential to be developed as a new approach for treating type II diabetes. (C) 2011 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。