(2-Methoxy-4-prop-2-enylphenyl) 3-methylbenzoate | 1017682-30-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: (2-Methoxy-4-prop-2-enylphenyl) 3-methylbenzoate
• CAS: 1017682-30-2
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: JHKVZCMLDNUPQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  间甲基苯甲酸 在 三溴甲基苯砜 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 生成 (2-Methoxy-4-prop-2-enylphenyl) 3-methylbenzoate
  参考文献：
  名称：

  新型 1-磺酰氧基/酰氧基丁香酚衍生物作为杀菌剂的组合合成

  摘要：

  背景： 开发高效、低风险的小分子绿色杀菌剂是有效控制植物病原真菌的关键。精油因其独特的来源和潜在的靶点，在新型杀菌剂发现中发挥着非常重要的作用。丁香酚是一种植物精油，主要从桃金娘科的丁香属植物的未开放和干燥的花蕾中分离得到。由于其独特的结构骨架，丁香酚及其衍生物展现出了广泛的生物活性。然而，关于合成新型1-磺酰氧基/酰氧基丁香酚衍生物作为对辣椒疫霉菌的杀菌剂的研究尚未报道。 方法： 制备了26种新型1-磺酰氧基/酰氧基丁香酚衍生物（3a-p和5a-j），并通过1H NMR、HRMS和熔点对其结构进行了良好的表征。使用菌丝生长速率法评估了它们对辣椒疫霉菌的杀菌活性。 结果： 为了寻找控制植物病原真菌的新型天然产物杀菌剂，我们设计和合成了两系列新型1-磺酰氧基/酰氧基丁香酚衍生物（3a-p和5a-j）作为对辣椒疫霉菌的杀菌剂。杀菌活性结果显示，在所有化合物中，特别是化合物3a、3f和3n，对辣椒疫霉菌的抗真菌活性最强，EC50值分别为79.05、75.05和70.80。 结论： 结果表明，磺酰氧基的丁香酚的抗真菌活性高于酰氧基。建议通过引入磺酰氧基来提高丁香酚的杀菌活性。这将为进一步设计、结构修饰和开发丁香酚衍生物作为杀菌剂铺平道路。

  DOI：

  10.2174/1386207324666210813114829

文献信息

• PERFUME PRECURSOR
  申请人：Takasago International Corporation

  公开号：EP3689849A1

  公开（公告）日：2020-08-05

  The present invention relates to a perfume precursor represented by formula (1). (In formula (1), R1 represents a hydrogen atom, a C1-C12 alkyl group, a hydroxy group, a methoxy group, or an ethoxy group; R2 represents a single bond, a C1-C2 alkylene group which may have a substituent, or a vinylene group which may have a substituent; R3 represents a residue obtained by removing one hydrogen atom of a hydroxy group from a C5-C20 perfume alcohol or a phenol which may have a substituent.)

  本发明涉及一种由式（1）表示的香水前体。(在式(1)中，R1 代表氢原子、C1-C12 烷基、羟基、甲氧基或乙氧基；R2 代表单键、可能具有取代基的 C1-C2 亚烷基或可能具有取代基的乙烯基；R3 代表通过从 C5-C20 香水醇或可能具有取代基的苯酚中去除羟基的一个氢原子而得到的残余物)。
• Design and synthesis of eugenol derivatives, as potent 15-lipoxygenase inhibitors
  作者：Hamid Sadeghian、Seyed Mohammad Seyedi、Mohammad Reza Saberi、Zahra Arghiani、Mehdi Riazi

  DOI：10.1016/j.bmc.2007.10.016

  日期：2008.1

  A group of 4-allyl-2-methoxyphenol (eugenol) esters were designed, synthesized, and evaluated as potential inhibitors of soybean 15-lipoxygenase (SLO). Compounds 4c, 4d 4f, 4p, and 4q showed the best IC50 in SLO inhibition (IC50 = 1.7, 2.3, 2.1, 2.2, and 0.017 mu M respectively). All compounds were docked into SLO active site and showed that ally) group of compounds is oriented toward the iron atom in the active site of SLO. It is assumed that lipophilic interaction of ligand-enzyme would be in charge of inhibiting the enzyme activity. The selectivity of eugenol derivatives in inhibiting 15-HLOb was also compared with 15-HLOa by molecular modeling and multiple alignment techniques. (C) 2007 Elsevier Ltd. All rights reserved.
• Combinatorial Synthesis of Novel 1-sulfonyloxy/acyloxyeugenol Derivatives as Fungicidal Agents
  作者：Zhiping Che、Genqiang Chen、Lina Zhu、Jiaxuan He、Song Zhang、Yuanhao Li、Xiaolong Guo、Di Sun、Yuee Tian、Shengming Liu、Xiaobo Huang

  DOI：10.2174/1386207324666210813114829

  日期：2022.8

  Developing the high-efficiency and low-risk small-molecule greenfungicide is the key to effective control of the plant pathogenic oomycetes. Essential oils play a very important role in novel fungicide discovery for their unique sources and potential target sites. Eugenol, a kind of plant essential oil, was mainly isolated from the unopened and dried flower buds of Syzygium aromaticum of the Myrtaceae family. Due to its unique structural skeleton, eugenol and its derivatives have exhibited a wide range of biological activities. However, a study on the synthesis of novel 1-sulfonyloxy/acyloxyeugenol derivatives as fungicidal agents against Phytophthora capsici has not yet been reported.

  Twenty-six novel 1-sulfonyloxy/acyloxyeugenol derivatives (3a-p and 5a-j) were prepared and their structures were well characterized by 1H NMR, HRMS, and m.p. Their fungicidal activity was evaluated against P. capsici by using the mycelial growth rate method.

  To find novel natural-product-based fungicidal agents to control the plant pathogenic oomycetes, we herein designed and synthesized two series of novel 1-sulfonyloxy/acyloxyeugenol derivatives (3a-p and 5a-j) as fungicidal agents against P. capsici Leonian, in vitro. Results of fungicidal activity revealed that, among all compounds, especially compounds 3a, 3f, and 3n displayed the most potent anti-oomycete activity against P. capsici with EC50 values of 79.05, 75.05, and 70.80, respectively.

  The results revealed that the anti-oomycete activity of eugenol with the sulfonyloxy group was higher than that with the acyloxy group. It is suggested that the fungicidal activity of eugenol can be improved by introducing the sulfonyloxy group. This will pave the way for further design, structural modification, and development of eugenol derivatives as fungicidal agents.

  背景： 开发高效、低风险的小分子绿色杀菌剂是有效控制植物病原真菌的关键。精油因其独特的来源和潜在的靶点，在新型杀菌剂发现中发挥着非常重要的作用。丁香酚是一种植物精油，主要从桃金娘科的丁香属植物的未开放和干燥的花蕾中分离得到。由于其独特的结构骨架，丁香酚及其衍生物展现出了广泛的生物活性。然而，关于合成新型1-磺酰氧基/酰氧基丁香酚衍生物作为对辣椒疫霉菌的杀菌剂的研究尚未报道。 方法： 制备了26种新型1-磺酰氧基/酰氧基丁香酚衍生物（3a-p和5a-j），并通过1H NMR、HRMS和熔点对其结构进行了良好的表征。使用菌丝生长速率法评估了它们对辣椒疫霉菌的杀菌活性。 结果： 为了寻找控制植物病原真菌的新型天然产物杀菌剂，我们设计和合成了两系列新型1-磺酰氧基/酰氧基丁香酚衍生物（3a-p和5a-j）作为对辣椒疫霉菌的杀菌剂。杀菌活性结果显示，在所有化合物中，特别是化合物3a、3f和3n，对辣椒疫霉菌的抗真菌活性最强，EC50值分别为79.05、75.05和70.80。 结论： 结果表明，磺酰氧基的丁香酚的抗真菌活性高于酰氧基。建议通过引入磺酰氧基来提高丁香酚的杀菌活性。这将为进一步设计、结构修饰和开发丁香酚衍生物作为杀菌剂铺平道路。