3-acetyl-2,4,6-trihydroxy-5-methylbenzaldehyde | 59677-81-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-acetyl-2,4,6-trihydroxy-5-methylbenzaldehyde
• 英文别名: 3-acetyl-2,4,6-trihydroxy-5-methyl-benzaldehyde；3-Acetyl-2,4,6-trihydroxy-5-methyl-benzaldehyd；3-Formyl-5-methyl-phloracetophenon；Benzaldehyde, 3-acetyl-2,4,6-trihydroxy-5-methyl-
• CAS: 59677-81-5
• 化学式: C₁₀H₁₀O₅
• 分子量: 210.186
• InChiKey: PKYIEWLPNIBZJS-UHFFFAOYSA-N

物化性质

• 熔点：
  155°C

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-acetyl-2,4,6-trihydroxy-5-methylbenzaldehyde 在 potassium hydroxide 作用下， 以 甲醇 、 乙醚 、 乙醇 、 水 、 乙酸乙酯 为溶剂， 反应 38.0h， 生成 3'-formyl-4',6'-dihydroxy-2'-methoxy-5'-methyl-2-fluorochalcone
  参考文献：
  名称：

  3'-甲酰基-4',6'-二羟基-2'-甲氧基-5'-甲基查尔酮 (FMC) 及其类似物的简明合成和细胞评价

  摘要：

  摘要 3'-甲酰基-4',6'-二羟基-2'-甲氧基-5'-甲基查尔酮(FMC)是从Cleistocalyx operculatus中分离得到的天然产物。首先开发了针对 FMC 及其四种类似物 (1b-1e) 的四步合成策略。所有化合物均由市售的 2,4,6-三羟基苯乙酮合成；在 Vilsmeier-Haack 条件下在 3' 位置进行甲酰化，然后在 5' 位置引入甲基。2'位选择性甲基化的关键步骤是通过三甲基甲硅烷基重氮甲烷（TMSCHN2）实现的。然后在氢氧化钾存在下通过克莱森-施密特反应使取代的芳香醛缩合。所有结构均通过 1H NMR、13C NMR 和高分辨率质谱确认。筛选 FMC 和类似物的抗增殖活性。图形概要

  DOI：

  10.1080/00397911.2014.930492
• 作为产物：
  描述：

  formyl acetyl phloroglucinol 在 盐酸 、 amalgamated zinc 作用下， 生成 3-acetyl-2,4,6-trihydroxy-5-methylbenzaldehyde
  参考文献：
  名称：

  740. C-甲基间苯三酚的新合成

  摘要：

  DOI：

  10.1039/jr9510003355

文献信息

• An Efficient Two-Step Synthesis of Jensenone Isolated from Eucalyptus jensenii. Synthesis of Analogues and Evaluation as Antioxidants
  作者：Sandip B. Bharate、Siddheshwar K. Chauthe、Kamlesh K. Bhutani、Inder P. Singh

  DOI：10.1071/ch05061

  日期：——

  A phloroglucinol derivative, jensenone (1) isolated from leaves of Eucalyptus jensenii has been synthesized for the first time through a short and efficient two-step procedure starting from commercially available phloroglucinol. The methodology provides a simplified route to introduce diformyl moiety for synthesis of biologically active formylated phloroglucinol compounds such as antimalarial robustadials

  一种从桉树叶中分离的间苯三酚衍生物 jensenone (1) 首次通过从市售间苯三酚开始的短而有效的两步程序合成。该方法提供了一种简化的途径来引入二甲酰基部分，以合成具有生物活性的甲酰化间苯三酚化合物，例如抗疟药、癌症化学预防 euglobals 和防污铁木糖醛。还合成了几种詹塞酮类似物并评估了抗氧化能力。
• Biomimetic synthesis, antimicrobial, antileishmanial and antimalarial activities of euglobals and their analogues
  作者：Sandip B. Bharate、Kamlesh K. Bhutani、Shabana I. Khan、Babu L. Tekwani、Melissa R. Jacob、Ikhlas A. Khan、Inder Pal Singh

  DOI：10.1016/j.bmc.2005.10.027

  日期：2006.3

  In the present communication, naturally occurring phloroglucinol-monoterpene adducts, euglobals G1-G4 (3b/a and 4a/b) and 16 new analogues (13a/b-18a/b and 19-22) were synthesized by biomimetic approach. These synthetic compounds differ from natural euglobals in the nature of monoterpene and acyl functionality. All of these compounds were evaluated for their antibacterial, antifungal, antileishmanial and antimalarial activities. Analogue 17b possessed good antibacterial activity against methicillin-resistant Staphylococcus aureus, while analogues 19-22 possessed potent antifungal activity against Candida glabrata with IC(50)s ranging from 1.5 to 2.5 mu g/mL. Euglobals along with all synthesized analogues exhibited antileishmanial activity. Amongst these, euglobal G2 (3a), G3 (4a) and analogues 13a and 14a showed potent antileishmanial activity with IC50s ranging from 2.8 to 3.9 mu g/mL. Analogue 16a possessed antimalarial activity against chloroquine sensitive D6 clone of Plasmodium falciparum. None of the compounds showed toxicity against mammalian kidney fibroblasts (vero cells) upto the concentration of 4.76 mu g/ml. (c) 2005 Elsevier Ltd. All rights reserved.