1,1-dimethylallyl coumarin | 1238397-19-7

• 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: 1,1-dimethylallyl coumarin
• 英文别名: 7-(2-methylbut-3-en-2-yloxy)-4-methyl-2H-chromen-2-one；7-(1,1-dimethyl-allyloxy)-4-methylcoumarin；4-Methyl-7-(2-methylbut-3-en-2-yloxy)chromen-2-one；4-methyl-7-(2-methylbut-3-en-2-yloxy)chromen-2-one
• CAS: 1238397-19-7
• 化学式: C₁₅H₁₆O₃
• 分子量: 244.29
• InChiKey: WNVNBCYEBNGWFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  1,1-dimethylallyl coumarin 在 C₄₁H₄₂N₄O₇ 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 84.0h， 生成 7-hydroxy-4-methyl-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one
  参考文献：
  名称：

  通过模拟酮类固醇异构酶催化二元体的设计螺旋寡酶催化剂加速芳香族克莱森重排

  摘要：

  设计了一系列氢键催化剂用于 1,1-二甲基烯丙基香豆素的芳香族克莱森重排。这些催化剂被设计为模拟酮类固醇异构酶中存在的两点氢键相互作用，该相互作用被提议用于稳定双键迁移过程中醚氧上形成的负电荷。1 两个氢键供体基团，一个苯酚醇和羧酸被接枝到构象限制的螺环支架上，它们一起将克莱森重排的速率比背景反应提高了 58 倍。理论计算正确地预测了最活跃的催化剂，并表明预组织和与反应过渡态的有利相互作用是观察到的速率提高的原因。

  DOI：

  10.1021/ja409214c
• 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 38.0h， 生成 1,1-dimethylallyl coumarin
  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

• Anti-AIDS agents 82: Synthesis of seco-(3′R,4′R)-3′,4′-di-O-(S)-camphanoyl-(+)-cis-khellactone (DCK) derivatives as novel anti-HIV agents
  作者：Jian Tang、Keduo Qian、Bei-Na Zhang、Ying Chen、Peng Xia、Donglei Yu、Yi Xia、Zheng-Yu Yang、Chin-Ho Chen、Susan L. Morris-Natschke

  DOI：10.1016/j.bmc.2010.04.089

  日期：2010.6.15

  value of 0.058 μM and a therapeutic index (TI) of 1000. The activity of 9 was better than that of 4-methyl DCK (2, EC50: 0.126 μM, TI: 301.2) in the same assay. Additionally, 9 also showed antiviral activity against a multi-RT inhibitor-resistant strain (RTMDR), which is insensitive to most DCK analogs. Compared with 2, compound 9 has a less complex structure, fewer hydrogen-bond acceptors, and a reduced

  十三新颖开环DCK类似物（4 - 16）配有几个新的骨架设计，合成和筛选的体外抗HIV-1活性。其中，三种化合物（5，13，和16）显示出中度的活性，和化合物9显示出与EC的最佳活性50 0.058μM的值和治疗指数的1000（TI）的活性9明显优于4-甲基 DCK ( 2 , EC 50 : 0.126 μM, TI: 301.2) 在相同的测定中。此外，9还对多 RT 抑制剂耐药菌株 (RTMDR) 显示出抗病毒活性，该菌株对大多数 DCK 类似物不敏感。与2相比，化合物9的结构更简单，氢键受体更少，log P值降低 。因此，它可能表现出更好的 ADME，并且似乎是作为抗 HIV 候选物进一步开发的有希望的新线索。
• 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.
• Acceleration of an Aromatic Claisen Rearrangement via a Designed Spiroligozyme Catalyst that Mimics the Ketosteroid Isomerase Catalytic Dyad
  作者：Matthew F. L. Parker、Sílvia Osuna、Guillaume Bollot、Shivaiah Vaddypally、Michael J. Zdilla、K. N. Houk、Christian E. Schafmeister

  DOI：10.1021/ja409214c

  日期：2014.3.12

  A series of hydrogen-bonding catalysts have been designed for the aromatic Claisen rearrangement of a 1,1-dimethylallyl coumarin. These catalysts were designed as mimics of the two-point hydrogen-bonding interaction present in ketosteroid isomerase that has been proposed to stabilize a developing negative charge on the ether oxygen in the migration of the double bond.1 Two hydrogen bond donating groups

  设计了一系列氢键催化剂用于 1,1-二甲基烯丙基香豆素的芳香族克莱森重排。这些催化剂被设计为模拟酮类固醇异构酶中存在的两点氢键相互作用，该相互作用被提议用于稳定双键迁移过程中醚氧上形成的负电荷。1 两个氢键供体基团，一个苯酚醇和羧酸被接枝到构象限制的螺环支架上，它们一起将克莱森重排的速率比背景反应提高了 58 倍。理论计算正确地预测了最活跃的催化剂，并表明预组织和与反应过渡态的有利相互作用是观察到的速率提高的原因。