7-(2-methyl-allyloxy)-4-methylcoumarin | 35817-32-4

• 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-allyloxy)-4-methylcoumarin
• 英文别名: 4-Methyl-7-(2-methylallyloxy)-2H-1-benzopyran-2-one；4-methyl-7-(2-methylprop-2-enoxy)chromen-2-one
• CAS: 35817-32-4
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: SXUHNEMTGMWMJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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-allyloxy)-4-methylcoumarin 在 N-甲基甲酰胺 、 水 作用下， 反应 0.37h， 以68%的产率得到7-Hydroxy-4-methyl-8-(2-methyl-allyl)-chromen-2-one
  参考文献：
  名称：

  Microwave and BF3 Promoted Rearrangement of Allyloxycoumarins to Allylcoumarins and Dihydrofurocoumarins

  摘要：

  DOI：

  10.3987/com-01-9265
• 作为产物：
  描述：

  间苯二酚 在 硫酸 、 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 31.0h， 生成 7-(2-methyl-allyloxy)-4-methylcoumarin
  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
• Iron(II)-catalyzed direct C H cyanoalkylation of 2H-indazoles and coumarins via radical C C bond cleavage
  作者：Pin Gao、Yuan-Bo Cheng、Fan Yang、Li-Na Guo、Xin-Hua Duan

  DOI：10.1016/j.tetlet.2019.150967

  日期：2019.8

  An iron-catalyzed C-3 cyanoalkylation of 2H-indazole and coumarin derivates with cyclobutanone oxime esters has been accomplished, which proceeds efficiently in a high regioselective manner to construct diverse alkylated 2H-indazole and coumarin derivates in moderate to good yields. Preliminary mechanistic studies reveal that a distal cyanosubstituted alkyl radicals intermediate would be formed through radical-involved C-C bond cleavage of cyclobutanone oximes ester. (C) 2019 Elsevier Ltd. All rights reserved.
• AGENT FOR PROMOTING OSTEOBLAST DIFFERENTIATION, PHARMACEUTICAL COMPOSITION FOR PROMOTING BONE FORMATION, AND FOOD FOR SPECIAL DIETARY USE CONTAINING AURAPTENE ANALOG AS ACTIVE INGREDIENT
  申请人：Woo Je-Tae

  公开号：US20130102796A1

  公开（公告）日：2013-04-25

  Agents or pharmaceutical compositions for promoting osteoblast differentiation include purified auraptene or coumarin analogs thereof represented by the following formula 1: wherein R1 represents a hydrogen, a hydroxy, a methoxy, a methyl, an ethyl, a propyl, a carboxyl, a carboxymethyl, or a carboxyethyl; R2 represents a hydrogen, a hydroxy, a methoxy, a methyl, an ethyl, a propyl, a carboxyl, a carboxymethyl, a carboxyethyl or a coumarinyl; R3 represents a hydrogen, a hydroxy, a methoxy, a methyl, an ethyl, a propyl, a carboxyl, a carboxymethyl or a carboxyethyl; and R4 represents a hydrogen, a C 1 -C 15 liner or branched alkyl, an alkenyl, an alkadienyl or an alkatrienyl.
• US8729279B2
  申请人：——

  公开号：US8729279B2

  公开（公告）日：2014-05-20