3,4-dimethyl-6-acetyl-7-hydroxycoumarin | 141497-71-4

• 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: 3,4-dimethyl-6-acetyl-7-hydroxycoumarin
• 英文别名: 6-acetyl-3,4-dimethyl-7-hydroxy-2H-1-benzopyran-2-one；6-acetyl-3,4-dimethyl-7-hydroxycoumarin；6-acetyl-7-hydroxy-3,4-dimethyl-coumarin；6-Acetyl-7-hydroxy-3,4-dimethyl-cumarin；6-Acetyl-7-hydroxy-3,4-dimethylchromen-2-one
• CAS: 141497-71-4
• 化学式: C₁₃H₁₂O₄
• 分子量: 232.236
• InChiKey: TXIBWXRMMHYQOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-dimethyl-6-acetyl-7-hydroxycoumarin 、 2-(三苯基膦亚基)丙酸甲酯 以 甲苯 为溶剂， 反应 40.0h， 以84%的产率得到3,4,6,7-tetramethylpyrano<3,2-g>chromene-2,8-dione
  参考文献：
  名称：

  Nicolaides, D. N.; Fylaktakidou, K. C.; Bezergiannidou-Balouktsi, C., Journal of Heterocyclic Chemistry, 1994, vol. 31, # 1, p. 173 - 176

  摘要：

  DOI：
• 作为产物：
  描述：

  二甲基伞形酮 在 三氯化铝 、 sodium acetate 作用下， 生成 3,4-dimethyl-6-acetyl-7-hydroxycoumarin
  参考文献：
  名称：

  Vedaldi; Dall'Acqua; Baccichetti, Il Farmaco, 1991, vol. 46, # 11, p. 1381 - 1406

  摘要：

  DOI：

文献信息

• Development and Preclinical Studies of Broad-Spectrum Anti-HIV Agent (3′<i>R</i>,4′<i>R</i>)-3-Cyanomethyl-4-methyl-3′,4′-di-<i>O</i>-(<i>S</i>)-camphanoyl-(+)-<i>cis</i>-khellactone (3-Cyanomethyl-4-methyl-DCK)
  作者：Lan Xie、Huan-Fang Guo、Hong Lu、Xiao-Mei Zhuang、An-Ming Zhang、Gang Wu、Jin-Xiu Ruan、Ting Zhou、Donglei Yu、Keduo Qian、Kuo-Hsiung Lee、Shibo Jiang

  DOI：10.1021/jm8003009

  日期：2008.12.25

  discovered that (3'R,4'R)-3-cyanomethyl-4-methyl-3',4'-di-O-(S)-camphanoyl-(+)-cis-khellactone (4, 3-cyanomethyl-4-methyl-DCK) showed promising anti-HIV activity. In these current studies, we developed and optimized successfully a practical 10-step synthesis for scale-up preparation to increase the overall yield of 4 from 7.8% to 32%. Furthermore, compound 4 exhibited broad-spectrum anti-HIV activity against

  在之前的研究中，我们发现 (3'R,4'R)-3-cyanomethyl-4-methyl-3',4'-di-O-(S)-camphanoyl-(+)-cis-khellactone (4 , 3-cyanomethyl-4-methyl-DCK) 显示出有希望的抗 HIV 活性。在这些当前的研究中，我们成功开发并优化了实用的 10 步合成，用于放大制备，将 4 的总产率从 7.8% 提高到 32%。此外，化合物 4 对 CD4+ T 细胞系和外周血单核细胞的野生型和耐药病毒感染表现出广谱抗 HIV 活性，这些病毒感染具有不同亚型和嗜性的实验室适应和原代 HIV-1 分离株. 进一步对化合物 4 进行体外和体内药代动力学研究。这些研究表明4具有中等的细胞渗透性，中等的口服生物利用度，和低系统清除率。这些结果表明，4 应该被开发为一种有前景的抗 HIV 药物，以作为临床试验候选药物进行开发。
• A solvent-free synthesis of coumarins using a Wells–Dawson heteropolyacid as catalyst
  作者：G.P. Romanelli、D. Bennardi、D.M. Ruiz、G. Baronetti、H.J. Thomas、J.C. Autino

  DOI：10.1016/j.tetlet.2004.09.183

  日期：2004.11

  Substituted coumarins are synthesized from phenols and beta-ketoesters by the Pechmann reaction, using a Wells-Dawson heteropolyacid (H(6)P(2)W(18)O(62)(.)24H(2)O) as catalyst by a solvent-free procedure. This one requires low reaction times, 130degreesC temperature and as little as 1 mol% of Wells-Dawson acid, obtaining good to excellent yields of coumarins. The catalyst showed to be reusable with no differences in the yields. The results are compared with those of the reactions performed in toluene solution. The presented synthetic procedure is a convenient, clean and fast alternative for synthesizing 4-substituted coumarins (17 examples). (C) 2004 Elsevier Ltd. All rights reserved.
• Vedaldi; Dall'Acqua; Baccichetti, Il Farmaco, 1991, vol. 46, # 11, p. 1381 - 1406
  作者：Vedaldi、Dall'Acqua、Baccichetti、Carlassare、Bordin、Rodighiero、Manzini、Guiotto

  DOI：——

  日期：——
• Nicolaides, D. N.; Fylaktakidou, K. C.; Bezergiannidou-Balouktsi, C., Journal of Heterocyclic Chemistry, 1994, vol. 31, # 1, p. 173 - 176
  作者：Nicolaides, D. N.、Fylaktakidou, K. C.、Bezergiannidou-Balouktsi, C.、Litinas, K. E.

  DOI：——

  日期：——