3-acetyl-8-methyl-coumarin | 116557-42-7

• 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: 3-acetyl-8-methyl-coumarin
• 英文别名: 3-Acetyl-8-methyl-cumarin；3-acetyl-8-methyl-2H-chromen-2-one；3-acetyl-8-methylchromen-2-one
• CAS: 116557-42-7
• 化学式: C₁₂H₁₀O₃
• 分子量: 202.21
• InChiKey: DNOHRUCKKQLLJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-acetyl-8-methyl-coumarin 在 乙醇 、 盐酸羟胺 、 水 作用下， 生成 3-(1-hydroxyimino-ethyl)-8-methyl-coumarin
  参考文献：
  名称：

  Chuit; Bolsing, Bulletin de la Societe Chimique de France, 1906, vol. <3> 35, p. 88

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 哌啶 作用下， 生成 3-acetyl-8-methyl-coumarin
  参考文献：
  名称：

  Chuit; Bolsing, Bulletin de la Societe Chimique de France, 1906, vol. <3> 35, p. 88

  摘要：

  DOI：

文献信息

• Synthesis, crystal structure, in vitro antifungal activity and molecular docking of 3-(1-((4H-1,2,4-triazol-4-yl)imino)ethyl)-2H-benzopyran-2-one derivatives
  作者：Yunrui Feng、Yun Hao、Yangming Dong、Yinghui Ren、Jie Huang、Xiaobin Zhang、Cuiling Wang

  DOI：10.1016/j.molstruc.2023.136735

  日期：2024.1

  novel 3-(1-((4H-1,2,4-triazol-4-yl)imino)ethyl)-2H-benzopyran-2-one derivatives (TEMC-1-TEMC-13) were synthesized. The structure of compounds were verified by NMR, IR and HRMS. The crystal structures of TEMC-6 and TEMC-12 were determined by single-crystal X-ray diffraction (XRD), they are monoclinic systems P21/c space group and triclinic systems, respectively P-1 space group and the crystal structure

  合成了13种新型3-(1-((4H-1,2,4-三唑-4-基)亚氨基)乙基)-2H-苯并吡喃-2-酮衍生物(TEMC- 1 - TEMC-13 )。化合物的结构通过NMR、IR、HRMS进行了验证。通过单晶X射线衍射(XRD)测定了TEMC-6和TEMC-12的晶体结构，它们分别为单斜晶系P2 1 /c空间群和三斜晶系，分别为P-1空间群，晶体结构显示分子间和分子内氢键的存在对活性效果起着重要作用。合成化合物对禾谷镰刀菌的体外抗真菌活性结果表明甲基和烷氧基取代的化合物具有良好的生物活性。其中TEMC-7的效果最好（EC 50  = 6.74 μg/mL），且商品药氟康唑（EC 50 =10.19 μg/mL）具有持久的抗真菌作用。分子对接用于预测配体与CYP51的结合模式。良好活性化合物的活性位点包括香豆素基团和残基TRY A:105、三唑基团和残基ALA A:291、以及席夫碱结构上的甲基和受体中心HEMA
• BF3·OEt2 Catalyzed Cascade [4 + 2] Benzannulation of Vinyloxiranes with Coumarins to Construct Benzocoumarin Derivatives
  作者：Yafei Wang、Yujia Wang、Jiaxin Qu、Tongtong Yang、Yining Zhang、Chunhao Yuan、Hongchao Guo、Chang Wang

  DOI：10.1021/acs.joc.4c00742

  日期：2024.7.5

  BF3·OEt2-catalyzed cascade cyclization reaction of vinyloxirane with coumarin is described, affording the benzocoumarin derivatives with moderate to excellent yields (72–92%). The reaction demonstrates exceptional substrate tolerance and has been extensively explored for its potential in drug development, including scale-up experiments, functional group transformations, and screening of the products for anticancer

  描述了 BF 3 ·OEt 2催化的乙烯基环氧乙烷与香豆素的级联环化反应，以中等至优异的收率 (72–92%) 提供苯并香豆素衍生物。该反应表现出卓越的底物耐受性，并因其在药物开发中的潜力而得到广泛探索，包括放大实验、官能团转化和产品抗癌活性筛选。此外，反应机制已通过中间捕获和控制实验得到严格验证。此外，该反应代表了不常见的非金属催化的乙烯基环氧乙烷分子间环化。
• Access to 4-Alkenylated Coumarins via Ruthenium-Catalyzed Olefinic C–H Alkenylation of Coumarins with Modifiable and Removable Directing Groups
  作者：Yu-Jiao Wang、Tong-Tong Wang、Lan Yao、Qian-Long Wang、Li-Ming Zhao

  DOI：10.1021/acs.joc.0c00249

  日期：2020.8.7

  The ruthenium-catalyzed activation of the C4 position of coumarins for coupling with acrylates was described using modifiable ketone as a directing group. The alkenylation reaction provided a direct approach to prepare previously inaccessible 4-alkenylated coumarins with operational simplicity and high atom-economy. This protocol also worked well with coumarin-3-carboxylic acids to unveil a rare instance of a tandem alkenylation/decarboxylation reaction. The potential value of this approach was further highlighted by the efficient synthesis of several heterocyclic fused coumarin derivatives.