4-(allylamino)coumarin | 138313-84-5

• 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
• 英文名称: 4-(allylamino)coumarin
• 英文别名: 4-(Prop-2-enylamino)chromen-2-one
• CAS: 138313-84-5
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: KTYVEZILJVZHFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(allylamino)coumarin 在 Grubbs catalyst first generation 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 84.0h， 生成 4-(2,5-dihydro-1H-pyrrol-1-yl)-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of (2,5-dihydro-1H-pyrrol-1-yl)-2H-chromen-2-ones as free radical scavengers

  摘要：

  The allylation of aminocoumarins in the presence of excess of anhydrous K2CO3 and allyl bromide to diallylaminocoumarins is described. The Ring Closing Metathesis reaction of the later with the Grubbs' 1rst generation catalyst under reflux or MW irradiation has resulted mainly to (2,5-dihydro-1H-pyrrol-1-yl)coumarins and (1H-pyrrol-1-yl)coumarins. The new compounds were tested in vitro for their ability: (i) to interact with 1,1-diphenyl-2-picryl-hydrazyl (DPPH) stable free radical, (ii) to inhibit lipid peroxidation, (iii) to scavenge the superoxide anion, (iv) to inhibit the activity of soybean lipoxygenase LO and (v) to scavenge hydroxyl radicals. Most of them were found to be potent lipid peroxidation inhibitors in vitro. The majority of the compounds showed significant hydroxyl radical scavenging activity. Compounds 11a and 12c presenting higher LO inhibitory activity as well as compound 17 were found to present a promising antioxidant and LO inhibitory profile. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.053
• 作为产物：
  描述：

  4-羟基香豆素 在 potassium carbonate 、 三乙胺 、 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 24.0h， 生成 4-(allylamino)coumarin
  参考文献：
  名称：

  通过自由基促进的烷基化分子内 C5 环化进入 4,5-稠合香豆素框架

  摘要：

  一种前所未有的自由基促进策略，涉及N-丙烯酰基-4-氨基香豆素的多米诺烷基化/分子内 C5 环化，已被设计用于组装 4,5-融合香豆素支架。该方案采用银催化的氧化脱羧作用从用作自由基前体的羧酸生成烷基自由基。该方法还扩展到由 2-含氧酸、1,3-二羰基化合物、异丙醇和丙酮产生的各种碳中心自由基。

  DOI：

  10.1039/d4ob00942h

文献信息

• Ivanov, Ivo C.; Karagiosov, Stoyan K.; Simeonov, Mario F., Liebigs Annalen der Chemie, 1992, # 3, p. 203 - 208
  作者：Ivanov, Ivo C.、Karagiosov, Stoyan K.、Simeonov, Mario F.

  DOI：——

  日期：——
• A Convenient Approach to the Synthesis of Dialkyl 5‐Oxo‐1,2‐dihydro‐5<i>H</i>‐chromeno [4,3‐<i>b</i>]pyridine‐2,3‐dicarboxylates
  作者：Toma N. Glasnov、Ivo C. Ivanov

  DOI：10.1080/00397910801929465

  日期：2008.4.1

  Coumarin and its analogs are considered privileged scaffolds in the current synthetic and pharmacological research. The chemical behavior of enaminocarbaldehydes of the coumarin moiety under intramolecular Wittig reaction conditions in the presence of triphenylphosphine and dimethyl or diethyl acetylenedicarboxylates has been studied, resulting in the isolation of a series of dimethyl and diethyl 5-oxo-1,2-dihydro-5H-chromeno[4,3-b]pyridine-2,3-dicarboxylates in good to high yields.
• Synthesis and biological evaluation of (2,5-dihydro-1H-pyrrol-1-yl)-2H-chromen-2-ones as free radical scavengers
  作者：Anna Balabani、Dimitra J. Hadjipavlou-Litina、Konstantinos E. Litinas、Maria Mainou、Crystal-Catherine Tsironi、Anastasia Vronteli

  DOI：10.1016/j.ejmech.2011.09.053

  日期：2011.12

  The allylation of aminocoumarins in the presence of excess of anhydrous K2CO3 and allyl bromide to diallylaminocoumarins is described. The Ring Closing Metathesis reaction of the later with the Grubbs' 1rst generation catalyst under reflux or MW irradiation has resulted mainly to (2,5-dihydro-1H-pyrrol-1-yl)coumarins and (1H-pyrrol-1-yl)coumarins. The new compounds were tested in vitro for their ability: (i) to interact with 1,1-diphenyl-2-picryl-hydrazyl (DPPH) stable free radical, (ii) to inhibit lipid peroxidation, (iii) to scavenge the superoxide anion, (iv) to inhibit the activity of soybean lipoxygenase LO and (v) to scavenge hydroxyl radicals. Most of them were found to be potent lipid peroxidation inhibitors in vitro. The majority of the compounds showed significant hydroxyl radical scavenging activity. Compounds 11a and 12c presenting higher LO inhibitory activity as well as compound 17 were found to present a promising antioxidant and LO inhibitory profile. (C) 2011 Elsevier Masson SAS. All rights reserved.
• 10.1039/d4ob00942h
  作者：Raji Reddy, Chada、Edhara, Venkatareddy、Kumari, Ankita、Patil, Amol D.、Thandavamurthy, Karthikeyan

  DOI：10.1039/d4ob00942h

  日期：——

  the assembly of 4,5-fused coumarin scaffolds. This protocol employs silver-catalyzed oxidative decarboxylation for the generation of alkyl radicals from carboxylic acids, which were used as radical precursors. This method has also been extended to a diverse range of carbon-centered radicals generated from 2-oxo acids, a 1,3-dicarbonyl compound, isopropanol and acetone.

  一种前所未有的自由基促进策略，涉及N-丙烯酰基-4-氨基香豆素的多米诺烷基化/分子内 C5 环化，已被设计用于组装 4,5-融合香豆素支架。该方案采用银催化的氧化脱羧作用从用作自由基前体的羧酸生成烷基自由基。该方法还扩展到由 2-含氧酸、1,3-二羰基化合物、异丙醇和丙酮产生的各种碳中心自由基。