1-(2,4,6-三羟基苯基)-1-己酮 | 5665-89-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2,4,6-三羟基苯基)-1-己酮
• 英文名称: 1-(2,4,6-trihydroxyphenyl)hexan-1-one
• 英文别名: 1-(2,4,6-trihydroxyphenyl)-1-hexanone；hexanoyl phloroglucinole；hexanoyl phloroglucinol；hexanoyl phloroglucin；1-(2,4,6-trihydroxy-phenyl)-hexan-1-one；1-(2,4,6-Trihydroxy-phenyl)-hexan-1-on
• CAS: 5665-89-4
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: RGMMTOZHCJCZRW-UHFFFAOYSA-N

物化性质

• 熔点：
  120-121 °C
• 沸点：
  374.9±22.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2914501900

反应信息

• 作为反应物：
  描述：

  1-(2,4,6-三羟基苯基)-1-己酮 在 盐酸 、 汞 、 锌 作用下， 以 乙醇 为溶剂， 反应 100.0h， 以74%的产率得到2-hexyl-phloroglucinol
  参考文献：
  名称：

  Mizobuchi, Shigeyuki; Sato, Yuko, Agricultural and Biological Chemistry, 1985, vol. 49, # 3, p. 719 - 724

  摘要：

  DOI：
• 作为产物：
  描述：

  在 水 作用下， 反应 1.5h， 生成 1-(2,4,6-三羟基苯基)-1-己酮
  参考文献：
  名称：

  A Test for Homology:  Photoactive Crystalline Assemblies Involving Linear Templates Based on a Homologous Series of Phloroglucinols

  摘要：

  Cocrystallization of trans-1,2-bis(4-pyridyl)ethylene (4,4'-bpe) with eight members of a homologous series of phloroglucinols 1a-h yields molecular solids 2(1a-h)-2(4,4'-bpe) with components held together by four O-H...N hydrogen bonds. In each case, the molecules assemble to form a discrete four-component assembly with olefins preorganized for a [2 + 2] photodimerization. UV irradiation of each member in the series of solids produces rctt-tetrakis(4-pyridyl)cyclobutane (4,4'-tpcb), stereospecifically, in up to 100% yield.

  DOI：

  10.1021/ol0484052

文献信息

• Synthesis of Novel 3-Alkyl-3′,4′,5,7-Tetrahydroxyflavones
  作者：Raquel S. G. R. Seixas、Diana C. G. A. Pinto、Artur M. S. Silva、José A. S. Cavaleiro

  DOI：10.1071/ch08162

  日期：——

  Novel 3-alkyl-3′,4′,5,7-tetrahydroxyflavones have been prepared. The synthetic strategy involves the preparation of 1-(2-hydroxy-4,6-dimethoxyphenyl)alkan-1-ones from the Friedel–Crafts acylation of phloroglucinol followed by methylation. These key compounds were submitted to the three-step Baker–Venkataraman method, giving the 3-alkyl-3′,4′,5,7-tetramethoxyflavones, which were demethylated with boron tribromide.

  新型 3-烷基-3′,4′,5,7-四羟基黄酮被制备出来。其合成策略是通过氯代葡萄糖醇的弗里德尔-卡夫斯酰化反应制备 1-(2-羟基-4,6-二甲氧基苯基)烷-1-酮，然后进行甲基化反应。这些关键化合物采用三步贝克-文卡塔拉曼法，得到了 3-烷基-3′,4′,5,7-四甲氧基黄酮，并用三溴化硼进行了脱甲基处理。
• Inhibitory Effect of Acylphloroglucinol Derivatives on the Replication of Vesicular Stomatitis Virus
  作者：Kazuhiro Chiba、Takako Takakuwa、Masahiro Tada、Takao Yoshii

  DOI：10.1271/bbb.56.1769

  日期：1992.1

  The antiviral activity of natural phloroglucinols and of synthesized mono- and diacylphloroglucinols, and 2,6-diacyl-4,4-dialkylcyclohexa-1,3,5-triones was investigated. A correlation between the acyl chain length and inhibitory activity against vesicular stomatitis virus (VSV) was observed. Potent antiviral activity was found in di-isovalerylphoroglucinol. 2,6-Diacyl-4,4-dialkylcyclohexa-1,3,5-triones inhibited replication of the virus with low cytotoxicity.

  研究了天然根皮酚类化合物、合成的一元和二元酰基根皮酚类化合物以及2,6-二酰基-4,4-二烷基环己-1,3,5-三酮的抗病毒活性。观察到酰基链长度与对水泡性口炎病毒（VSV）的抑制活性之间的相关性。二异戊酰基根皮酚显示出强大的抗病毒活性。2,6-二酰基-4,4-二烷基环己-1,3,5-三酮具有抑制病毒复制和低细胞毒性的特点。
• Synthesis and biological evaluation of novel myrtucommulones and structural analogues that target mPGES-1 and 5-lipoxygenase
  作者：Katja Wiechmann、Hans Müller、Volker Huch、David Hartmann、Oliver Werz、Johann Jauch

  DOI：10.1016/j.ejmech.2015.06.001

  日期：2015.8

  The natural acylphloroglucinol myrtucommulone A (1) inhibits microsomal prostaglandin E2 synthase (mPGES)-1 and 5-lipoxygenase (5-LO), and induces apoptosis of cancer cells. Starting from 1 as lead, 28 analogues were synthesized following a straightforward modular strategy with high yielding convergent steps. Major structural variations concerned (I) replacement of the syncarpic acid moieties by dimedone

  天然酰基间苯三酚Myrtucommulone A（1）抑制微粒体前列腺素E 2合酶（mPGES）-1和5-脂氧合酶（5-LO），并诱导癌细胞凋亡。从1个铅开始，按照简单的模块化策略合成了28个类似物，并产生了高收率的收敛步骤。主要的结构变化涉及（I）用二甲基二酮或茚满二酮取代同型二羧酸部分，（II）用酰基间苯三酚核心将同型二羧酸环化，以及（III）用异丙基，异丁基，n取代次甲基桥和酰基残基-戊基或苯基。抑制mPGES-1的效力提高了12.5倍，达到43（2-（1-（3-己基-2,4,6-三羟基-5-（1-（3-羟基-1-氧代-1H-茚满-2-基）-2-甲基丙基）苯基）-2 -甲基丙基）-3-羟基-1H-茚满-1-酮，IC 50  = 0.08μM，5-LO抑制作用被47（2-（（3-hexanoyl-2,4,6-具有IC 50的三羟基-5-（（3-羟基-1-氧代-1H-茚满-2-基）（苯基
• Total Synthesis of Myrtucommulone A
  作者：Hans Müller、Michael Paul、David Hartmann、Volker Huch、Dagmar Blaesius、Andreas Koeberle、Oliver Werz、Johann Jauch

  DOI：10.1002/anie.200903906

  日期：2010.3.8

  In a one‐step conversion, commercially available or known compounds are connected to form myrtucommulone A, an anti‐inflammatory and apoptosis‐inducing substance from the common myrtle Myrtus communis (see scheme). This strategy can be used, as well to prepare myrtucommulone libraries.

  通过一步转换，将市售的或已知的化合物连接起来，形成桃金娘木酮A，这是一种常见的桃金娘Myrtus communis的抗炎和凋亡诱导物质（请参阅方案）。也可以使用此策略来准备myrtucommulone库。
• Synthesis and antibiotic activity of novel acylated phloroglucinol compounds against methicillin-resistant Staphylococcus aureus
  作者：Navriti Mittal、Haben H. Tesfu、Andrew M. Hogan、Silvia T. Cardona、John L. Sorensen

  DOI：10.1038/s41429-019-0153-4

  日期：2019.5

  The rise in antibiotic resistance among pathogenic microorganisms has created an imbalance in the drugs available for treatment, in part due to the slow development of new antibiotics. Cystic fibrosis (CF) patients are highly susceptible to antibiotic-resistant pathogens, including methicillin-resistant Staphylococcus aureus (MRSA). Phloroglucinols and related polyketide natural products have demonstrated antimicrobial activity against a number of Gram-positive bacteria including S. aureus. In this study, we investigated a series of acylated phloroglucinol derivatives to determine their potential as lead compounds for the design of novel therapeutics. To assess the activity of these compounds, we determined the minimum inhibitory and bactericidal concentration (MIC and MBC, respectively), the minimum biofilm inhibitory and biofilm eradication concentration (MBIC and MBEC, respectively), and evaluated hemolytic activity, as well as their interaction with clinically relevant antibiotics. Of the 12 compounds tested against MRSA and methicillin-susceptible strains, four showed MIC values ranging from 0.125 to 8 µg ml−1 and all of them were bactericidal. However, none of the compounds were able to eradicate biofilms at the concentrations tested. Three of the four did not display hemolytic activity under the conditions tested. Further studies on the interactions of these compounds with clinically relevant antibiotics showed that phlorodipropanophenone displayed synergistic activity when paired with doxycycline. Our results suggest that these acylated phloroglucinols have potential for being further investigated as antibacterial leads.

  病原微生物中抗生素抗性的上升造成了治疗用药物的不平衡，这在一定程度上是由于新抗生素的研发缓慢。囊性纤维化(CF)患者极易感染抗生素抗性病原体，包括耐甲氧西林金黄色葡萄球菌(MRSA)。间苯三酚类及其相关多酮天然产物已显示出对多种革兰氏阳性细菌(包括金黄色葡萄球菌)的抗菌活性。在本研究中，我们调查了一系列酰化间苯三酚衍生物质，以确定它们作为新型治疗药物设计的先导化合物的潜力。为了评估这些化合物的活性，我们测定了最低抑制浓度和杀菌浓度(MIC和MBC)、最低生物膜抑制浓度和生物膜消除浓度(MBIC和MBEC)，并评估了溶血活性，以及它们与临床相关抗生素的相互作用。在针对MRSA和甲氧西林敏感菌株测试的12种化合物中，有4种的MIC值在0.125至8 µg/ml之间，且均为杀菌性。然而，在测试的浓度下，这些化合物均无法消除生物膜。其中3种在测试条件下未显示溶血活性。进一步研究这些化合物与临床相关抗生素的相互作用，结果显示，苯二丙酸苯酮在配伍强力霉素时表现出协同活性。我们的结果表明，这些酰化间苯三酚具有作为抗菌先导物进一步研究的潜力。