2,3-二溴-4,5-二羟基苄醇 | 4950-06-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 2,3-二溴-4,5-二羟基苄醇
• 英文名称: lanosol
• 英文别名: 3,4-dibromo-5-(hydroxymethyl)benzene-1,2-diol；2,3-dibromo-4,5-dihydroxybenzyl alcohol；2,3-dibromo-4,5-dihydroxybenzylalcohol；3,4-dibromo-5-(hydroxymethyl)pyrocatechol；3.4-Dihydroxi-5.6-dibromo-benzylalkohol；2,3-Dibrom-4,5-dihydroxy-benzylalkohol
• CAS: 4950-06-5
• 化学式: C₇H₆Br₂O₃
• 分子量: 297.931
• InChiKey: GKZCMEUEEFOXIJ-UHFFFAOYSA-N

物化性质

• 熔点：
  136 °C
• 沸点：
  408.8±40.0 °C(Predicted)
• 密度：
  2.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  2,3-二溴-4,5-二羟基苄醇 在 硫酸 、 溴 作用下， 以 乙醚 、 氯仿 为溶剂， 生成 3,4,3',4'-Tetrabrom-5,5'-methylendibrenzcatechin-tetramethylether
  参考文献：
  名称：

  Lundgren,L. et al., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1979, vol. 33, p. 105 - 108

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-二溴-4-羟基-5-甲氧基苯甲醛 在 sodium tetrahydroborate 、 氢溴酸 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 2,3-二溴-4,5-二羟基苄醇
  参考文献：
  名称：

  Sudalai, A.; Rao, G. S. Krishna, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1989, vol. 28, # 1-11, p. 858 - 859

  摘要：

  DOI：

文献信息

• Total Synthesis of the Biologically Active, Naturally Occurring 3,4-Dibromo-5-[2-bromo-3,4-dihydroxy-6-(methoxymethyl)benzyl]benzene-1,2-diol and Regioselective O-Demethylation of Aryl Methyl Ethers
  作者：Yusuf Akbaba、Halis Türker Balaydın、Süleyman Göksu、Ertan Şahin、Abdullah Menzek

  DOI：10.1002/hlca.200900300

  日期：——

  4‐Dibromo‐5‐[2‐bromo‐3,4‐dihydroxy‐6‐(methoxymethyl)benzyl]benzene‐1,2‐diol (2), a natural product, has been synthesized for the first time starting from (3‐bromo‐4,5‐dimethoxyphenyl)methanol (5) in five steps and with an overall yield of 34%. The reaction of some methoxymethyl‐substituted aryl methyl ethers with BBr3, followed by the addition of MeOH, afforded the corresponding methoxymethyl‐substituted arylphenols

  天然产物3,4-二溴-5- [2-溴-3,4-二羟基-6-（甲氧基甲基）苄基]苯1,2-二醇（2）首次从（3-溴-4,5-二甲氧基苯基）甲醇（5）分五个步骤，总产率为34％。一些甲氧基甲基取代的芳基甲基醚与BBr 3的反应，然后添加MeOH，可以高收率得到相应的甲氧基甲基取代的芳基酚。
• Reexamination of the bromophenols in the red alga Rhodomela larix
  作者：Boris Weinstein、Tracy L. Rold、Clayton E. Harrell、Mark W. Burns、J.Robert Waaland

  DOI：10.1016/0031-9422(75)85247-2

  日期：1975.12

  Abstract A reinvestigation of the red alga Rhodomela larix gave dipotassium 2,3-dibromo-5-hydroxy-benzyl-1′,4-disulfate and 2,3-dibromo-4,5-dihydroxybenzy] methyl ether. Aqueous hydrolysis of the salt yielded 2,3-dibromo-4,5-dihydroxybenzyl alcohol. Simple phenols reported in algae are probably artifacts of the isolation procedure.

  摘要 对红藻落叶松进行再研究，得到了 2,3-二溴-5-羟基-苄基-1',4-二硫酸二钾和 2,3-二溴-4,5-二羟基苄基] 甲基醚。盐的水水解产生2,3-二溴-4,5-二羟基苄醇。藻类中报告的简单酚类可能是分离过程的产物。
• Compositions that include a triterpene and a carrier
  申请人：Krasutsky A. Pavel

  公开号：US20060003948A1

  公开（公告）日：2006-01-05

  The present invention provides for compositions that includes a triterpene (e.g., betulin) and a carrier (e.g., lanolin). The compositions are useful for skin care (e.g., as cosmetic formulations), and as therapeutic formulations, e.g., for treating topical fungal infections.

  本发明提供了包括三萜（如白桦脂）和载体（如羊毛脂）的组合物。这些组合物可用于皮肤护理（如化妆品配方）和治疗配方，如治疗局部真菌感染。
• Vitamin C in organic synthesis: reaction with p-hydroxybenzyl alcohol derivatives
  作者：Andrew J. Poss、Randolph K. Belter

  DOI：10.1021/jo00242a037

  日期：1988.4
• In<i>-</i>vitro Cytotoxic Activities of the Major Bromophenols of the Red Alga<i> Polysiphonia </i><i>l</i><i>anosa</i> and Some Novel Synthetic Isomers
  作者：Nagwa A. Shoeib、Michael C. Bibby、Gerald Blunden、Peter A. Linley、David J. Swaine、Richard T. Wheelhouse、Colin W. Wright

  DOI：10.1021/np0305268

  日期：2004.9.1

  Bioassay-guided fractionation was applied to the cytotoxic chloroform fraction of the red alga Polysiphonia lanosa, The major compounds of the most active fraction were identified using GLC-MS analysis as lanosol (1), methyl, ethyl, and n-propyl ethers of lanosol (1a, 1b, and 1c, respectively), and aldehyde of lanosol (2), although 1b appears to be an artifact arising during the fractionation procedure. These compounds and other known bromophenols were synthesized in addition to four novel isomers (3, 3a-c). The cytotoxic activities of all the synthetic compounds were determined against DLD-1 cells using the MTT assay. Compounds with IC50 < 20 mumol were also tested against HCT-116 cells. Compound 3c (2,5-dibromo-3,4-dihydroxybenzyl n-propyl ether) was the most active compound against both cell lines (IC50 = 1.72 and 0.80 mumol, respectively), and its effect on the cell cycle was studied using flow cytometry.

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