4-羟基-4-(甲氧基羰基甲基)环己酮 | 81053-14-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-羟基-4-(甲氧基羰基甲基)环己酮
• 英文名称: methyl 1-hydroxy-4-oxocyclohexanacetate
• 英文别名: Methyl 2-(1-hydroxy-4-oxocyclohexyl)acetate
• CAS: 81053-14-7
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: UYLWRBIQRPNVNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  jacaranone 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以79%的产率得到4-羟基-4-(甲氧基羰基甲基)环己酮
  参考文献：
  名称：

  Isolation and structure–activity relationship studies of jacaranones: Anti-inflammatory quinoids from the Cuban endemic plant Jacaranda arborea (Bignoniaceae)

  摘要：

  The Cuban endemic plant Jacaranda arborea (Bignoniaceae) has been traditionally used in folk medicine as an acaricide and for acne treatment. Two known quinoids, methyl (1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)acetate (jacaranone) (1) and its ethyl ester 2 were isolated from this species as anti-inflammatory substances. Compound 1 prominently inhibited the production of TNF-alpha in both LPS-treated macrophages and mice, with low toxicity. Structure-activity relationship studies revealed that the high electrophilicity of 1 as a Michael acceptor played an important role in these effects. Unlike in previous studies, such as those on antitumor, anti-oxidant, and anti-malarial activities, ester derivatives of 1 retained their potent anti-inflammatory activity. Our results suggest that jacaranones may target specific biomacromolecule(s) at lower concentrations than hitherto expected to exhibit potent activities. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2020.152005

文献信息

• Isolation and structure–activity relationship studies of jacaranones: Anti-inflammatory quinoids from the Cuban endemic plant Jacaranda arborea (Bignoniaceae)
  作者：Minako Hirukawa、Menghua Zhang、Lazaro M. Echenique–Diaz、Koji Mizota、Satoshi D. Ohdachi、Gerardo Begué–Quiala、Jorge L. Delgado–Labañino、Jorgelino Gámez–Díez、José Alvarez–Lemus、Leandro Galano Machado、Miguel Suárez Núñez、Takahiro Shibata、Hideo Kigoshi、Masaki Kita

  DOI：10.1016/j.tetlet.2020.152005

  日期：2020.6

  The Cuban endemic plant Jacaranda arborea (Bignoniaceae) has been traditionally used in folk medicine as an acaricide and for acne treatment. Two known quinoids, methyl (1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)acetate (jacaranone) (1) and its ethyl ester 2 were isolated from this species as anti-inflammatory substances. Compound 1 prominently inhibited the production of TNF-alpha in both LPS-treated macrophages and mice, with low toxicity. Structure-activity relationship studies revealed that the high electrophilicity of 1 as a Michael acceptor played an important role in these effects. Unlike in previous studies, such as those on antitumor, anti-oxidant, and anti-malarial activities, ester derivatives of 1 retained their potent anti-inflammatory activity. Our results suggest that jacaranones may target specific biomacromolecule(s) at lower concentrations than hitherto expected to exhibit potent activities. (C) 2020 Elsevier Ltd. All rights reserved.