4-(3',3'-dimethylallyloxy)coumarin | 31490-69-4

• 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: 4-(3',3'-dimethylallyloxy)coumarin
• 英文别名: 4-(3-Methylbut-2-enoxy)chromen-2-one
• CAS: 31490-69-4
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: FUFAEBGONGEKMI-UHFFFAOYSA-N

物化性质

• 熔点：
  98 °C
• 沸点：
  397.6±42.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：

  4-(3',3'-dimethylallyloxy)coumarin 以 二苯醚 为溶剂， 以70%的产率得到2,3,3-Trimethyl-2,3-dihydro-furo[3,2-c]chromen-4-one
  参考文献：
  名称：

  Patra, Amarendra; Mukhopadhyay, Apurba K.; Mitra, Alok K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 1167 - 1170

  摘要：

  DOI：
• 作为产物：
  描述：

  4-羟基香豆素 生成 4-(3',3'-dimethylallyloxy)coumarin
  参考文献：
  名称：

  SHAH R. R.; TRIVEDI K. N., CURR. SCI (INDIA) , 1975, 44, NO 7, 226-227

  摘要：

  DOI：

文献信息

• In(OTf)₃-catalysed easy access to dihydropyranocoumarin and dihydropyranochromone derivatives
  作者：Naouel Boufroua、Elisabet Dunach、Fabien Fontaine-Vive、Samia Achouche-Bouzroura、Sophie Poulain-Martini

  DOI：10.1039/d0nj00080a

  日期：——

  Allylation/cyclization of β-ketolactone-type heterocyclic compounds, under In(OTf)₃-catalysis, for the construction of biologically active dihydropyranocoumarin and dihydropyranochromone derivatives.

  β-酮内酯类杂环化合物的烯丙基化/环化反应，在In(OTf)₃催化下进行，用于构建具有生物活性的二氢吡喃香豆素和二氢吡喃色酮衍生物。
• Domino conversions of allyl tetronates and 4-allyloxycoumarins to all-trans 1,3,4,5-tetrasubstituted γ-butyrolactams
  作者：Rainer Schobert、Arno Bieser、Gillian Mullen、Gary Gordon

  DOI：10.1016/j.tetlet.2005.06.055

  日期：2005.8

  All-trans 1,3,4,5-tetrasubstituted γ-butyrolactams 3 and 7 are readily available in one-pot from allyl tetronates or 4-allyloxycoumarins and amines via a four-step domino Claisen–Conia ring-opening transamidation reaction.

  全反式1,3,4,5-四取代的γ-丁内酰胺3和7可通过四步多米诺骨牌Claisen-Conia开环转氨反应一锅得自烯丙基四价酸酯或4-烯丙氧基香豆素和胺。
• Design, Synthesis, and Biological Activities of Novel Coumarin Derivatives as Pesticide Candidates
  作者：Henan Ma、Kaihua Wang、Beibei Wang、Ziwen Wang、Yuxiu Liu、Qingmin Wang

  DOI：10.1021/acs.jafc.3c08161

  日期：2024.3.6

  solve this problem. The creation of new pesticides based on natural products is an important and effective method. Herein, coumarins were selected as parent structures, and a series of their derivatives were designed, synthesized, and evaluated for their antiviral activities, fungicidal activities, and insecticidal activities. We found that coumarin derivatives exhibited good to excellent antiviral

  粮食安全是21世纪的重要问题；防治农作物病虫害是解决这一问题的关键。以天然产物为基础创造新农药是一种重要而有效的方法。本文以香豆素为母体结构，设计、合成了一系列其衍生物，并评价了其抗病毒活性、杀菌活性和杀虫活性。我们发现香豆素衍生物对烟草花叶病毒（TMV）表现出良好至优异的抗病毒活性。 500 μg/mL 时， I-1 、 I-2a 、 I-4b 、 II-2c 、 II-2g 、 II-3和II-3b的抗病毒活性优于利巴韦林。分子对接研究表明这些化合物与TMV CP有很强的相互作用。这些化合物还对 14 种植物病原真菌表现出广谱杀菌活性。 I-1 、 I-2a 、 I-3c和II-2d对禾谷丝核菌、梨轮纹菌、核盘菌和稻瘟病菌的 EC 50值在 1.56–8.65 μg/mL 范围内。大多数化合物还对粘虫表现出良好的杀虫活性。农药相似性分析表明，这些化合物具有农药相似性，有潜力开发为候选农
• Inhibition of reverse transcriptase and Taq DNA polymerase by compounds possessing the coumarin framework
  作者：A. Garro Hugo、M. Manzur Jimena、M. Ciuffo Gladys、E. Tonn Carlos、R. Pungitore Carlos

  DOI：10.1016/j.bmcl.2013.12.104

  日期：2014.2

  Coumarin derivatives were prepared using natural products isolated from plants belonging in the Pterocaulon genus (Asteraceae) and commercial drugs. Some molecules have displayed interesting activity against myeloid murine leukemia virus-reverse transcriptase (MMLV-RT) (compounds 20 and 28 produced inhibition with IC50 values of 38.62 and 50.98 mu M, respectively) and Taq DNA polymerase (analogues 13 and 14 produced inhibition with IC50 values of 48.08 and 57.88 mu M, respectively). Such inhibitors may have importance as antiretroviral chemotherapeutic agents and also in the development of anticancer drugs. (C) 2013 Elsevier Ltd. All rights reserved.
• 4-Hydroxycoumarin and Related Systems: Sitoselectivity of the Mitsunobu Reaction with Prenyl Alcohols
  作者：Giancarlo Cravotto、Gian Mario Nano、Giovanni Palmisano、Silvia Tagliapietra

  DOI：10.3987/com-03-9737

  日期：——

  The Mitsunobu reaction leads to the formation of new C-C bonds between prenyl alcohols and 1,3-dicarbonyl compounds like 4-hydroxycoumarin or its nitrogen isoster. Buchapine was obtained through a one-pot procedure from 4-hydroxy-2-quinolone and dimethylallyl alcohol.