6-烯丙氧基-4-甲基-色烯-2-酮 | 90207-15-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 6-烯丙氧基-4-甲基-色烯-2-酮
• 英文名称: 4-methyl-6-allyloxycoumarin
• 英文别名: 6-Allyloxy-4-methyl-cumarin；6-allyloxy-4-methyl-chromen-2-one；6-Allyloxy-4-methylcoumarin；4-methyl-6-prop-2-enoxychromen-2-one
• CAS: 90207-15-1
• 化学式: C₁₃H₁₂O₃
• mdl: MFCD02215591
• 分子量: 216.236
• InChiKey: ZCDCGUYMOOCLSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-烯丙氧基-4-甲基-色烯-2-酮 以 乙二醇 为溶剂， 反应 16.0h， 以78%的产率得到5-allyl-6-hydroxy-4-methyl-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of fused oxepinocoumarins as free radicals scavengers

  摘要：

  Some fused dihydrooxepino[f]-, [g]-, and [h]coumarins were obtained from the ring-closing metathesis of the corresponding o-allyl-allyloxycoumarins under the treatment with the first generation Grubbs' catalyst. These compounds were tested in vitro for their antioxidant activity, and they present significant scavenging activity. They were also showed to inhibit in vitro soybean lipoxygenase.

  DOI：

  10.3109/14756366.2011.555944
• 作为产物：
  描述：

  4-甲氧基苯酚 在 硫酸 、 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 36.0h， 生成 6-烯丙氧基-4-甲基-色烯-2-酮
  参考文献：
  名称：

  从相应的羟基香豆素合成 6- 和 7-烷氧基-4- 甲基香豆素及其转化为 6- 和 7-烷氧基-4- 甲酰基香豆素衍生物

  摘要：

  摘要 以对苯二酚和间苯二酚与乙酰乙酸乙酯反应制备了4-甲基-2H-色烯-2-酮的羟基衍生物。然后通过与烷基卤反应将这些羟基香豆素转化为相应的烷氧基衍生物。6-和7-烷氧基-4-甲基香豆素3a-i 和4a-i 的产率为55-95%。在常规和微波辅助加热条件下用二氧化硒氧化这些化合物产生相应的 4-甲酰基化合物 5b-h 和 6b-h，产率分别为 40-67% 和 90-93%。几种 6- 和 7-烷氧基-4-甲基香豆素 3a-i、4a-i 以及几乎所有 6- 和 7-烷氧基-4-甲酰基香豆素 5b-h、6b-h 都是新化合物。图形概要

  DOI：

  10.1080/00397911.2020.1807571

文献信息

• Synthesis and Biological Evaluation of Novel Hybrid Molecules Containing Purine, Coumarin and Isoxazoline or Isoxazole Moieties
  作者：Michael G. Kallitsakis、Angelo Carotti、Marco Catto、Aikaterini Peperidou、Dimitra J. Hadjipavlou-Litina、Konstantinos E. Litinas

  DOI：10.2174/1874104501711010196

  日期：2017.11.30

  INTRODUCTION The 1,3-dipolar cycloaddition reactions of nitrile oxides formed in situ (in the presence of NCS and Et3N) from the oximes of (purin-9-yl)acetaldehyde or (coumarinyloxy)acetaldehyde with allyloxycoumarins or 9-allylpurines, respectively resulted in 3,5-disubstituted isoxazolines. The similar reactions of propargyloxycoumarins or 9-propargylpurines led to 3,5-disubstituted isoxazoles by

  引言 由 (purin-9-yl) 乙醛或 (香豆素氧基) 乙醛的肟与烯丙氧基香豆素或 9-烯丙基嘌呤原位形成的腈氧化物（在 NCS 和 Et3N 存在下）的 1,3-偶极环加成反应分别导致在 3,5-二取代异恶唑啉中。炔丙基氧基香豆素或 9-炔丙基嘌呤的类似反应通过 PIDA 和催化量的 TFA 处理产生 3,5-二取代异恶唑。方法 将新化合物作为抗氧化剂和大豆脂氧合酶 LO、AChE 和 MAO-B 的抑制剂进行体外试验。结果大多数化合物显示出显着的羟基自由基清除活性。化合物4k和4n表现出LO抑制活性。结论 化合物 13e 具有结合抗 LO、抗 AChE 和抗 MAO-B 活性的抗氧化显着特征。
• Mild and efficient deprotection of allyl ethers of phenols and hydroxycoumarins using a palladium on charcoal catalyst and ammonium formate
  作者：Nemai C. Ganguly、Sanjoy Dutta、Mrityunjoy Datta

  DOI：10.1016/j.tetlet.2006.05.176

  日期：2006.8

  An efficient procedure for the cleavage of allyl phenyl ethers and allyl coumarinyl ethers using a catalytic amount of 10% Pd/C in combination with ammonium formate is described. Allyl ethers of phenols are deprotected in preference to those of alcohols and this method is compatible with several reducible functional groups such as CHO, COCH3, CO2Et and NHCOCH3.

  描述了一种催化量为10％的Pd / C与甲酸铵相结合的烯丙基苯基醚和烯丙基香豆基醚裂解的有效方法。酚的烯丙基醚比醇的烯丙基醚优先脱保护，并且该方法与几种可还原的官能团如CHO，COCH 3，CO 2 Et和NHCOCH 3相容。
• Synthesis of purine homo-N-nucleosides modified with coumarins as free radicals scavengers^*
  作者：Michael G. Kallitsakis、Dimitra J. Hadjipavlou-Litina、Konstantinos E. Litinas

  DOI：10.3109/14756366.2012.684050

  日期：2013.8.1

  Cross metathesis (CM) of 9-butenylpurines with 4-butenyloxycoumarin in the presence of Grubbs 2nd generation catalyst under MW irradiation resulted to conjugated compounds containing homo-N-nucleosides and coumarins. Analogous derivatives received by the CM reaction of 9-butenyl-6-piperidinylpurine with 6-or 7-butenyloxycoumarins, allyloxycoumarins or coumarinyl acrylate. These compounds were tested in vitro for their antioxidant activity and they present significant scavenging activity. The presence of a pentenyloxy moiety, the attachment position on coumarin ring as well as a purine homo-N-nucleoside group are considered as important structural features.
• Synthesis of 6- and 7-alkoxy-4-methylcoumarins from corresponding hydroxy coumarins and their conversion into 6- and 7-alkoxy-4-formylcoumarin derivatives
  作者：Vu Ngoc Toan、Nguyen Dinh Thanh

  DOI：10.1080/00397911.2020.1807571

  日期：2020.12.1

  Abstract Hydroxy derivatives of 4-methyl-2H-chromen-2-one were prepared from hydroquinone and resorcinol through their reaction with ethyl acetoacetate. These hydroxy coumarins were then converted into corresponding alkoxy derivatives by reaction with alkyl halides. The yields of 6- and 7-alkoxy-4-methylcoumarins 3a–i and 4a–i were 55−95%. Oxidation of these compounds by selenium dioxide under conventional

  摘要 以对苯二酚和间苯二酚与乙酰乙酸乙酯反应制备了4-甲基-2H-色烯-2-酮的羟基衍生物。然后通过与烷基卤反应将这些羟基香豆素转化为相应的烷氧基衍生物。6-和7-烷氧基-4-甲基香豆素3a-i 和4a-i 的产率为55-95%。在常规和微波辅助加热条件下用二氧化硒氧化这些化合物产生相应的 4-甲酰基化合物 5b-h 和 6b-h，产率分别为 40-67% 和 90-93%。几种 6- 和 7-烷氧基-4-甲基香豆素 3a-i、4a-i 以及几乎所有 6- 和 7-烷氧基-4-甲酰基香豆素 5b-h、6b-h 都是新化合物。图形概要
• Synthesis and biological evaluation of fused oxepinocoumarins as free radicals scavengers
  作者：Konstantinos E. Litinas、Alexandros Mangos、Thomas E. Nikkou、Dimitra J. Hadjipavlou-Litina

  DOI：10.3109/14756366.2011.555944

  日期：2011.12.1

  Some fused dihydrooxepino[f]-, [g]-, and [h]coumarins were obtained from the ring-closing metathesis of the corresponding o-allyl-allyloxycoumarins under the treatment with the first generation Grubbs' catalyst. These compounds were tested in vitro for their antioxidant activity, and they present significant scavenging activity. They were also showed to inhibit in vitro soybean lipoxygenase.