7-[(2-methyl-2-propenyl)oxy]-2H-chromen-2-one | 314262-25-4

• 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: 7-[(2-methyl-2-propenyl)oxy]-2H-chromen-2-one
• 英文别名: 7-(2-methyl-allyloxy)coumarin；7-[(2-methylprop-2-en-1-yl)oxy]-2H-chromen-2-one；7-(2-methylprop-2-enoxy)chromen-2-one
• CAS: 314262-25-4
• 化学式: C₁₃H₁₂O₃
• mdl: MFCD01546678
• 分子量: 216.236
• InChiKey: NYYIJXQZJGQQOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 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：

  7-[(2-methyl-2-propenyl)oxy]-2H-chromen-2-one 在 臭氧 、 N,N-二乙基苯胺 作用下， 以 甲醇 为溶剂， 反应 4.33h， 生成 7-hydroxy-8-(2-oxopropyl)-2H-chromen-2-one
  参考文献：
  名称：

  异补骨脂素的硫代和氧代类似物的合成

  摘要：

  通过克莱森重排的烯丙基芳基醚，然后在合适的溶剂存在下进行还原性臭氧分解，合成了一系列新颖的5'-取代的7-氧代和7-硫代异补骨脂素。在某些情况下，二甲基硫代氨基甲酰氯用作保护基并引入硫醇部分。

  DOI：

  10.1016/s0040-4020(02)00161-8
• 作为产物：
  描述：

  (乙氧基羰基甲基)三苯基氯化膦 在 potassium carbonate 、 potassium iodide 、 potassium hydroxide 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 25.5h， 生成 7-[(2-methyl-2-propenyl)oxy]-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis and anthelmintic activity of osthol analogs against Dactylogyrus intermedius in goldfish

  摘要：

  In an attempt to develop novel anthelmintic agents, our previously isolated osthol was used as lead structures for further optimization. In our research, a series of coumarin analogs, prepared from 7-hydroxy coumarin or 7-hydroxy-4-methyl coumarin, have been evaluated for their anthelmintic activities. In all of the compounds, 6 and 7 were first synthesized, and their structures were identified based on NMR and MS values. Among the candidates, 8-allyl-7-allyloxycoumarin showed better anthelmintic activity than other compounds against Dactylogyrus infestation with EC50 value of 1.81 mg/L The quantitative structure-activity relationship (QSAR) of 16 osthol analogs with anthelmintic activity expressed as pEC(50) and toxicity to goldfish expressed pLC(50), such results can offer useful theoretical references for future experimental works. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.009

文献信息

• Synthesis and biological evaluation of novel coumarin derivatives in rhabdoviral clearance
  作者：Yang Hu、Lipeng Shan、Tianxiu Qiu、Lei Liu、Jiong Chen

  DOI：10.1016/j.ejmech.2021.113739

  日期：2021.11

  industry. Therefore, in this study, IHNV was studied as a model to evaluate the antiviral activity of 35 novel coumarin derivatives. Coumarin A9 was specifically selected for further validation studies upon comparing the half maximum inhibitory concentration (IC50) of four screened candidate derivatives in epithelioma papulosum cyprinid (EPC) cells, as it exhibited an IC50 value of 2.96 μM against IHNV. The

  由弹状病毒引起的疾病对整个人类的生产生活产生了巨大影响。主要问题是缺乏治疗该病毒家族的药物。IHN的病原体传染性造血坏死病毒（IHNV）是一种典型的弹状病毒，给鲑鱼产业造成了巨大损失。因此，在本研究中，研究了 IHNV 作为评估 35 种新型香豆素衍生物抗病毒活性的模型。香豆素A9是专门于半最大抑制浓度（IC比较选择用于进一步的验证研究50在上皮瘤papulosum鲤科（EPC）的细胞筛选4种候选的衍生物），因为它表现出的IC 50对 IHNV 的值为 2.96 μM。数据显示，A9 处理显着抑制了 EPC 细胞中病毒诱导的细胞病变效应 (CPE)。另外，A9显示IC 50其他两种弹状病毒的值分别为 1.68 和 2.12 μM，即鲤鱼春季病毒血症和鲑鱼弹状病毒。此外，我们的结果表明 A9 发挥抗病毒活性，但不是通过破坏病毒颗粒和干扰 IHNV 的吸附。此外，我们发现 A9 对 IHNV 诱导的
• Microwave and BF3 Promoted Rearrangement of Allyloxycoumarins to Allylcoumarins and Dihydrofurocoumarins
  作者：Mohammad R. Saidi、Fatemeh Rajabi

  DOI：10.3987/com-01-9265

  日期：——
• Enzyme Activity Fingerprinting with Substrate Cocktails
  作者：Jean-Philippe Goddard、Jean-Louis Reymond

  DOI：10.1021/ja0478330

  日期：2004.9.1

  In the postgenomic era, emphasis is shifting from protein identification to protein functional analysis. Enzyme function can be characterized by measuring activity across series of substrates, which generates an activity profile or fingerprint. Activity fingerprinting is particularly useful to differentiate closely related enzymes. Previously reported fingerprinting methods use series of parallel measurements, which are complex and difficult to reproduce. Here we report a new method for fingerprinting enzyme activities based on using mixtures of substrates, or substrate cocktails, in a single reaction that is then analyzed by HPLC. The fingerprints produced are highly reproducible and allow functional differentiation and classification of closely related enzymes, as demonstrated for a series of lipases and esterases. The method is practical, general, and flexible in terms of reaction conditions and can be adapted to any reaction type.
• Synthesis and anthelmintic activity of osthol analogs against Dactylogyrus intermedius in goldfish
  作者：Guang-Lu Liu、Bing Hao、Shao-Peng Liu、Gao-Xue Wang

  DOI：10.1016/j.ejmech.2012.06.009

  日期：2012.8

  In an attempt to develop novel anthelmintic agents, our previously isolated osthol was used as lead structures for further optimization. In our research, a series of coumarin analogs, prepared from 7-hydroxy coumarin or 7-hydroxy-4-methyl coumarin, have been evaluated for their anthelmintic activities. In all of the compounds, 6 and 7 were first synthesized, and their structures were identified based on NMR and MS values. Among the candidates, 8-allyl-7-allyloxycoumarin showed better anthelmintic activity than other compounds against Dactylogyrus infestation with EC50 value of 1.81 mg/L The quantitative structure-activity relationship (QSAR) of 16 osthol analogs with anthelmintic activity expressed as pEC(50) and toxicity to goldfish expressed pLC(50), such results can offer useful theoretical references for future experimental works. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Synthesis of thio- and oxo-analogues of isopsoralen
  作者：Dino J Clarke、Ross S Robinson

  DOI：10.1016/s0040-4020(02)00161-8

  日期：2002.4

  A range of novel 5′-substituted 7-oxo and 7-thioisopsoralens were synthesized via a Claisen rearranged allyl aryl ether followed by reductive ozonolysis in the presence of a suitable solvent. In some cases dimethylthiocarbamoyl chloride was used as a protecting group and to introduce the thiol moiety.

  通过克莱森重排的烯丙基芳基醚，然后在合适的溶剂存在下进行还原性臭氧分解，合成了一系列新颖的5'-取代的7-氧代和7-硫代异补骨脂素。在某些情况下，二甲基硫代氨基甲酰氯用作保护基并引入硫醇部分。