6-(diallylamino)-2H-chromen-2-one | 1073539-34-0

• 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: 6-(diallylamino)-2H-chromen-2-one
• 英文别名: N,N-diallyl-6-aminocoumarin；6-[Bis(prop-2-enyl)amino]chromen-2-one；6-[bis(prop-2-enyl)amino]chromen-2-one
• CAS: 1073539-34-0
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: LLQCUXSXWNANLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(diallylamino)-2H-chromen-2-one 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 0.2h， 以95%的产率得到6-(2H-pyrrol-1(5H)-yl)-2H-chromen-2-one
  参考文献：
  名称：

  New Efficient RCM-Mediated Synthesis of Pyrrolidine Derivatives

  摘要：

  Fast and effective ring-closing olefin metathesis (RCM) of diallyamine derivatives of coumarin, quinolone, pyridine, and substituted benzene, using first-generation RCM ruthenium-based catalyst, leads to corresponding pyrrolidine derivatives in 70-95% yields under very mild conditions.

  DOI：

  10.1080/00397910802109240
• 作为产物：
  描述：

  6-硝基香豆素 在 甲酸 、 palladium 10% on activated carbon 、 potassium carbonate 、 三乙胺 作用下， 以 丙酮 为溶剂， 反应 5.0h， 生成 6-(diallylamino)-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

文献信息

• Sequential Aza-Claisen Rearrangement and Ring-Closing Metathesis as a Route to 1-Benzazepine Derivatives
  作者：Shital Chattopadhyay、Debalina Ghosh、Latibuddin Thander、Sanjay Ghosh

  DOI：10.1055/s-0028-1087298

  日期：2008.12

  A synthetic strategy based on sequential application of aza-Claisen rearrangement and ring-closing metathesis reaction as key steps has been developed for the synthesis of various 1-benzazepine derivatives of pharmaceutical relevance.

  基于 aza-Claisen 重排和闭环复分解反应的顺序应用作为关键步骤的合成策略已被开发用于合成各种与药物相关的 1-苯并氮杂衍生物。
• 10.1055/3-0028-1083311
  作者：Majumdar, Krishna C.、Chakravorty, Santanu、Shyam, Pranab Kr、Taher, Abu

  DOI：10.1055/3-0028-1083311

  日期：——
• New Efficient RCM-Mediated Synthesis of Pyrrolidine Derivatives
  作者：Krishna C. Majumdar、Santanu Chakravorty、Abu Taher

  DOI：10.1080/00397910802109240

  日期：2008.8.29

  Fast and effective ring-closing olefin metathesis (RCM) of diallyamine derivatives of coumarin, quinolone, pyridine, and substituted benzene, using first-generation RCM ruthenium-based catalyst, leads to corresponding pyrrolidine derivatives in 70-95% yields under very mild conditions.
• 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.