3-(3-hydroxy-4-methoxyphenyl)prop-2-yn-1-oic acid | 1267949-32-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-(3-hydroxy-4-methoxyphenyl)prop-2-yn-1-oic acid
• 英文别名: 3-(3-Hydroxy-4-methoxyphenyl)prop-2-ynoic acid；3-(3-hydroxy-4-methoxyphenyl)prop-2-ynoic acid
• CAS: 1267949-32-5
• 化学式: C₁₀H₈O₄
• 分子量: 192.171
• InChiKey: RXZZHRRHRGFCOG-UHFFFAOYSA-N

物化性质

• 沸点：
  409.8±45.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3-hydroxy-4-methoxyphenyl)prop-2-yn-1-oic acid 、 邻苯三酚 以 三氟乙酸 为溶剂， 以53.7%的产率得到7,8-dihydroxy-4-(3-hydroxy-4-methoxyphenyl)-3,4-dihydrocoumarin
  参考文献：
  名称：

  Synthesis and antimicrobial activities of 4-aryl-3,4-dihydrocoumarins and 4-arylcoumarins

  摘要：

  通过取代肉桂酸和3-芳基炔酸与相应的酚反应，合成了一系列4-芳基-3,4-二氢香豆素和4-芳基香豆素。这些化合物在体外评估了抗菌活性。合成的化合物对金黄色葡萄球菌、大肠杆菌、痢疾杆菌和白色念珠菌（真菌）表现出不同程度的抗微生物活性。具有羟基苯环和7,8-取代二羟基的A环化合物是最活跃的抗微生物剂。

  DOI：

  10.1007/s10600-012-0149-9
• 作为产物：
  描述：

  3-羟基-4-甲氧基肉桂酸 在 氯化亚砜 、 溴 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 12.33h， 生成 3-(3-hydroxy-4-methoxyphenyl)prop-2-yn-1-oic acid
  参考文献：
  名称：

  Synthesis and antimicrobial activities of 4-aryl-3,4-dihydrocoumarins and 4-arylcoumarins

  摘要：

  通过取代肉桂酸和3-芳基炔酸与相应的酚反应，合成了一系列4-芳基-3,4-二氢香豆素和4-芳基香豆素。这些化合物在体外评估了抗菌活性。合成的化合物对金黄色葡萄球菌、大肠杆菌、痢疾杆菌和白色念珠菌（真菌）表现出不同程度的抗微生物活性。具有羟基苯环和7,8-取代二羟基的A环化合物是最活跃的抗微生物剂。

  DOI：

  10.1007/s10600-012-0149-9

文献信息

• 一种4-芳基香豆素类化合物的制备方法
  申请人：山东省医学科学院药物研究所

  公开号：CN106187969B

  公开（公告）日：2019-03-26

  本发明涉及化学合成领域，具体的说是一种4‑芳基香豆素类化合物的制备方法，其特点是以取代苯甲醛为起始原料，与丙二酸生成取代苯基丙烯酸化合物；取代苯丙烯酸化合物经过加成、消除等反应或经过乙酰化保护酚羟基后再进行溴代、消除反应合成取代苯丙炔酸化合物；以硫酸酸化的蒙脱土K‑10为催化剂，取代苯基丙炔酸化合物与酚类化合物加热反应生成4‑芳基香豆素类化合物。与现有技术相比，本发明的4‑芳基香豆素类化合物的制备方法具有原料廉价易得、操作简单、催化剂可回收利用、绿色环保、后处理简单、生产成本较低等特点，具有很好的推广应用价值。
• Antioxidant and antitumor activities of 4-arylcoumarins and 4-aryl-3,4-dihydrocoumarins
  作者：Keyun Zhang、Weixian Ding、Jie Sun、Bin Zhang、Fujiao Lu、Ren Lai、Yong Zou、Gabriel Yedid

  DOI：10.1016/j.biochi.2014.03.014

  日期：2014.12

  Five 4-arylcoumarins (1c-g) and twelve 3,4-dihydro-4-arylcoumarins (2a-l) were synthesized and tested for antioxidant activity, antitumor activity, toxicity and structure-activity relationships analysis. 4-Arylcoumarins and 3,4-dihydro-4-arylcoumarins that possess two hydroxyl groups in ortho position, such as 1d, 1f, 2a, 2f, 2g and 2h had stronger radical scavenging properties than that of vitamin C (Vit C) in ABTS(center dot+) assay. Kinetic traces of scavenging ABTS(center dot+) and DPPH radicals showed that all the reaction could reached endpoint in 1 min, which was similar with Vit C. 4-Arylcoumarins with 3'-hydroxyl-4'-methylphenyl structural show more efficient NO center dot radical scavenging activity. Three compounds 2e, 1f and 2a, in particular had superior EC50 for NO center dot scavenging than did Vit C. MTT assay indicated that one compound in particular had a potential antitumor effect, inhibiting proliferation of BGC-823 cells and almost completely killing them at a concentration 62.5 mg/L. With same concentration 100 mu g/mL, hemolytic analysis in rabbit red blood cells showed that only two compounds had hemolytic activity with a little more than 5% hemolysis. Injection and oral toxicity tests on Galleria mellonella larvae showed that none of the tested 4-arylcoumarins significantly affected their appetite, viability and mortality. (C) 2014 Elsevier B.V. and Societe francaise de biochimie et biologie Moleculaire (SFBBM). All rights reserved.
• Efficient synthesis and biological evaluation of 4-arylcoumarin derivatives
  作者：Jie Sun、Wei Xian Ding、Ke Yun Zhang、Yong Zou

  DOI：10.1016/j.cclet.2010.12.017

  日期：2011.6

  Two bioactive natural 4-arylcoumarins, 5,7,4'-trimethoxy-4-phenylcoumarin (1a), 5,7-dimethoxy-4-phenylcoumarin (1b) and five closely related derivatives 1c-g were synthesized. In vitro evaluation with a catechol subunit for antioxidant and antimicrobial activity, these compounds using standard methods showed that compounds id, if displayed promise radical scavenging activity and if was found to be the most active one against Bacillus dysenteriae. (C) 2010 Yong Zou. Published by Elsevier BAT. on behalf of Chinese Chemical Society. All rights reserved.
• Synthesis and antimicrobial activities of 4-aryl-3,4-dihydrocoumarins and 4-arylcoumarins
  作者：Jie Sun、Wei-Xian Ding、Xiao-Ping Hong、Ke-Yun Zhang、Yong Zou

  DOI：10.1007/s10600-012-0149-9

  日期：2012.3

  A new series of 4-aryl-3,4-dihydrocoumarins and 4-arylcoumarins were synthesized by the reaction of substituted cinnamic acids and 3-arylpropiolic acid with the corresponding phenols. These compounds were evaluated for antibacterial activity in vitro. The synthesized compounds displayed different degrees of antimicrobial activity against Staphylococcus aureus, Escherichia coli, and Bacillus dysenteriae, and Candida albicans (a fungus). Compounds with catechol moieties and 7,8-substituted dihydroxyls in the A ring were the most active antimicrobial agents.

  通过取代肉桂酸和3-芳基炔酸与相应的酚反应，合成了一系列4-芳基-3,4-二氢香豆素和4-芳基香豆素。这些化合物在体外评估了抗菌活性。合成的化合物对金黄色葡萄球菌、大肠杆菌、痢疾杆菌和白色念珠菌（真菌）表现出不同程度的抗微生物活性。具有羟基苯环和7,8-取代二羟基的A环化合物是最活跃的抗微生物剂。