1-isopentyl-2,4,6-trihydroxybenzene | 26104-00-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1-isopentyl-2,4,6-trihydroxybenzene
• 英文别名: 2-isopentyl-phloroglucinol；2.4.6-Trihydroxy-1-isopentyl-benzol；2-Isopentyl-phloroglucin；Desacetyl-desmethyl-dihydro-acronylin；2-Isoamyl-phloroglucin；Isopentyl-phloroglucin；2-Isoamylphloroglucinol；2-(3-methylbutyl)benzene-1,3,5-triol
• CAS: 26104-00-7
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: KEXFTBDIYZFKGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-isopentyl-2,4,6-trihydroxybenzene 在 盐酸 、 potassium carbonate 、 zinc(II) chloride 作用下， 以 丙酮 为溶剂， 生成 4,6-Dibenzyloxy-2-hydroxy-3-isopentyl-acetophenon
  参考文献：
  名称：

  Radhakrishnan,P.V.; Rao,A.V.R., Indian Journal of Chemistry, 1966, vol. 4, p. 406 - 412

  摘要：

  DOI：
• 作为产物：
  描述：

  prenylphloroglucinol 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 生成 1-isopentyl-2,4,6-trihydroxybenzene
  参考文献：
  名称：

  Mitteldorf,R.; Riedl,W., Chemische Berichte, 1960, vol. 93, p. 309 - 312

  摘要：

  DOI：

文献信息

• cis- and trans-Tetrahydroisohumulones
  作者：W. J. G. Donnelly、P. V. R. Shannon

  DOI：10.1039/j39700000524

  日期：——

  Repeated acylation of phloroglucinol followed by intermediate reduction gave 4-deoxytetrahydrohumulone (VI), which was, by procedures of known type, converted into a mixture of (±)-cis- and (±)-trans-tetrahydroisohumulones [racemates of (XIX) and (XX) respectively]. The isomers were separated by chromatography and differentiated by their u.v. and 220 MHz n.m.r. spectra.

  将间苯三酚重复酰化，然后进行中间还原，得到4-脱氧四氢hydro草酮（VI），通过已知类型的方法将其转化为（±）-顺式-和（±）-反式-四氢异hu草酮[（XIX的外消旋物）的混合物和（XX）]。通过色谱分离异构体，并通过其uv和220 MHz nmr光谱进行区分。
• 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。
• Gruber, Chemische Berichte, 1942, vol. 75, p. 29,31
  作者：Gruber

  DOI：——

  日期：——
• Riedl; Leucht, Chemische Berichte, 1958, vol. 91, p. 2784,2792
  作者：Riedl、Leucht

  DOI：——

  日期：——
• Antiprotozoal and antimicrobial activities of O-alkylated and formylated acylphloroglucinols
  作者：Sandip B. Bharate、Shabana I. Khan、Nafees A.M. Yunus、Siddheshwar K. Chauthe、Melissa R. Jacob、Babu L. Tekwani、Ikhlas A. Khan、Inder Pal Singh

  DOI：10.1016/j.bmc.2006.10.006

  日期：2007.1.1

  In the present article, we examined the antileishmanial, antimalarial, antibacterial, and antifungal activities of several newly synthesized O-alkylated phloroglucinol compounds (11-19) which are analogues of the naturally occurring antimalarial compound 1. Analogues 12 and 16 exhibited antileishmanial activity against, Leishmania donovani promastigotes with IC(50)s of 5.3 and 4.2 mu g/mL, respectively. Naturally occurring monomeric formylated acylphloroglucinol compounds, grandinol (2), jensenone (3), and their analogues (29-37), were also synthesized and evaluated for antileishmanial, antimalarial, antibacterial, and antifungal activities. Amongst these, both grandinol and jensenone showed mild to moderate antibacterial, antifungal, and antileishmanial activities. Jensenone (3) was effective against Candida albicans with an IC50 of 5.5 mu g/mL but was ineffective against Cryptococcus neoformans and methicillin-resistant Staphylococcus aureus. Among the analogues, 34 was the most active against C albicans and C. neoformans with IC(50)s of 2.0 and 2.5 mu g/mL, respectively, and was fungicidal toward Candida albicans. (c) 2006 Elsevier Ltd. All rights reserved.