3-(3-methylphenoxy)-3-oxopropanoic acid | 114223-13-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 3-(3-methylphenoxy)-3-oxopropanoic acid
• 英文别名: malonic acid mono-m-tolyl ester；Malonsaeure-mono-m-tolylester；3-(3-Methylphenoxy)-3-oxopropanoic acid
• CAS: 114223-13-1
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: QIWAXZUXJSHGDH-UHFFFAOYSA-N

物化性质

• 熔点：
  52-54 °C
• 沸点：
  361.4±25.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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-(3-methylphenoxy)-3-oxopropanoic acid 在 Eaton’s reagent 作用下， 反应 5.0h， 生成 4-羟基-7-甲基香豆素
  参考文献：
  名称：

  通过3-烯丙基-4-羟基香豆素的钯催化分子内烷氧羰基化反应选择性合成4,5-二氢-6H-氧庚啶[3,2-c]色烯-2,6（3H）-二酮

  摘要：

  这项工作提出了一种区域选择性途径，以高产率和高区域选择性合成与香豆素骨架融合的七元环内酯。另外，羰基化反应不需要酸性条件，并且可以在不存在任何其他添加剂（例如氢（H 2））的情况下进行。

  DOI：

  10.1002/ejoc.201900649
• 作为产物：
  描述：

  丙二酸 在 氯化亚砜 、 乙醚 作用下， 生成 3-(3-methylphenoxy)-3-oxopropanoic acid
  参考文献：
  名称：

  Matsui; Ota, Nippon Kagaku Zasshi, 1957, vol. 78, p. 517,518

  摘要：

  DOI：

文献信息

• Synthesis and evaluation of antibacterial and anti-inflammatory properties of naturally occurring coumarins
  作者：Jabrane Azelmat、Serena Fiorito、Vito Alessandro Taddeo、Salvatore Genovese、Francesco Epifano、Daniel Grenier

  DOI：10.1016/j.phytol.2015.08.008

  日期：2015.9

  Coumarins are a group of heterocyclic compounds naturally present in a large variety of plant families. Nevertheless, oxyprenylated coumarins have been only recently seen as valuable and promising biologically active phytochemicals. In this study, we synthesized three naturally occurring O-prenylcoumarins (1), (2), and (3), and evaluated their antibacterial and anti-inflammatory properties in view of their therapeutic potential against periodontal disease. The three O-prenylcoumarins were synthesized using well-known schemes leading to the chromen-2-one nucleus. The periodontal pathogen Porphyromonas gingivalis was found to be highly susceptible to all three O-prenylcoumarins with minimal inhibitory concentration values in the range of 12.5-25 mg/ml; the non-prenylated forms of the coumarins did not show any activity. The antibacterial activity of (1), (2), and (3) appeared to result from its ability to permeate the cell membrane. Using the U937-3xkB-LUC human monocytic cell line, compounds (2) and (3) dose-dependently inhibited lipopolysaccharide-induced NF-kB activation, while (1) did not. The non-prenylated forms of the coumarins were either inactive or much less potent. In conclusion, O-prenylcoumarins (2) and (3) by exhibiting a dual mode of action including antibacterial and anti-inflammatory activities may represent promising targeted therapeutic agents for localized treatment of periodontal diseases. (C) 2015 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.
• Regioselective Synthesis of 4,5-Dihydro-6<i>H</i> -oxepino[3,2-<i>c</i> ]chromene-2,6(3<i>H</i> )-diones through Palladium-Catalyzed Intramolecular Alkoxycarbonylation of 3-Allyl-4-hydroxycoumarins
  作者：D. Oliver Sosa、Karla Almaraz、Manuel Amézquita-Valencia

  DOI：10.1002/ejoc.201900649

  日期：2019.8.7

  This work presents a regioselective route to synthesize seven‐membered ring lactones fused to coumarin scaffold in good yields and high regioselectivity. Additionality, the carbonylation reaction does not require acidic conditions and proceeds in the absence of any other additive such as hydrogen (H2).

  这项工作提出了一种区域选择性途径，以高产率和高区域选择性合成与香豆素骨架融合的七元环内酯。另外，羰基化反应不需要酸性条件，并且可以在不存在任何其他添加剂（例如氢（H 2））的情况下进行。
• Matsui; Ota, Nippon Kagaku Zasshi, 1957, vol. 78, p. 517,518
  作者：Matsui、Ota

  DOI：——

  日期：——