3,4-dibromo-5-(methoxymethyl)benzene-1,2-diol | 14045-42-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4-dibromo-5-(methoxymethyl)benzene-1,2-diol
• 英文别名: 2,3-dibromo-4,5-dihydroxybenzyl methyl ether；α-O-methyllanosol；lanosol methyl ether；3.4-Dihydroxi-5.6-dibromo-methylenoximethylbenzol；2,3-Dibrom-4,5-dihydroxy-α-methoxy-toluol；2,3-Dibrom-4,5-dihydroxy-benzyl-methylether
• CAS: 14045-42-2
• 化学式: C₈H₈Br₂O₃
• 分子量: 311.958
• InChiKey: SOPOZEAOODNSCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-dibromo-5-(methoxymethyl)benzene-1,2-diol 、 硫酸二甲酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 2,3-Dibrom-4,5-dimethoxy-benzyl-methyl-ether
  参考文献：
  名称：

  5,6-二溴原儿茶醛和2,3-二溴-4,5-二羟基苄基甲基醚

  摘要：

  从红色藻类Rhodomela larix中分离出了两种新的二溴酚，它们分别是5,6-二溴原儿茶醛和2,3-二溴-4,5-二羟基苄基甲基醚。

  DOI：

  10.1016/0040-4020(67)85068-3
• 作为产物：
  描述：

  5-溴香兰素 在 钾硼氢 、 溴 、 三溴化硼 、 铁粉 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 32.0h， 生成 3,4-dibromo-5-(methoxymethyl)benzene-1,2-diol
  参考文献：
  名称：

  In-vitro Cytotoxic Activities of the Major Bromophenols of the Red Alga Polysiphonia lanosa and Some Novel Synthetic Isomers

  摘要：

  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.

  DOI：

  10.1021/np0305268

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。
• KUBO, ISAO;OCHI, MASAMITSU;SHIBATA, KOZO;HANKE, FREDERICK J.;NAKATSU, TET+, J. NATUR. PROD., 53,(1990) N, C. 50-56
  作者：KUBO, ISAO、OCHI, MASAMITSU、SHIBATA, KOZO、HANKE, FREDERICK J.、NAKATSU, TET+

  DOI：——

  日期：——
• 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.
• 5,6-dibromoprotocatechualdehyde and 2,3-dibromo-4,5-dihydroxybenzyl methyl ether
  作者：N. Katsui、Y. Suzuki、S. Kitamura、T. Irie

  DOI：10.1016/0040-4020(67)85068-3

  日期：1967.1

  Two new dibromophenols have been isolated from a red alga Rhodomela larix and are shown to be 5,6-dibromoprotocatechualdehyde and 2,3-dibromo-4,5-dihydroxybenzyl methyl ether.

  从红色藻类Rhodomela larix中分离出了两种新的二溴酚，它们分别是5,6-二溴原儿茶醛和2,3-二溴-4,5-二羟基苄基甲基醚。