2-(4-bromo-3-methoxy-benzyloxy)-tetrahydro-pyran | 17100-70-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-bromo-3-methoxy-benzyloxy)-tetrahydro-pyran
• 英文别名: 4-Brom-3-methoxybenzyl-tetrahydropyranylether；2-[(4-Bromo-3-methoxyphenyl)methoxy]oxane；2-[(4-bromo-3-methoxyphenyl)methoxy]oxane
• CAS: 17100-70-8
• 化学式: C₁₃H₁₇BrO₃
• 分子量: 301.18
• InChiKey: BVQWOEOAMQKBFR-UHFFFAOYSA-N

物化性质

• 沸点：
  375.4±42.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-bromo-3-methoxy-benzyloxy)-tetrahydro-pyran 在 盐酸 、 四(三苯基膦)钯 、 正丁基锂 、 18-冠醚-6 、 四溴化碳 、 5%-palladium/activated carbon 、 水 、 氢气 、 sodium methylate 、 三溴化硼 、 sodium carbonate 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 甲苯 为溶剂， -40.0~20.0 ℃ 、300.01 kPa 条件下， 反应 144.5h， 生成 4-[(Dimethylamino)methyl]-14-oxapentacyclo[20.2.2.210,13.115,19.02,7]nonacosa-1(24),2(7),3,5,10(29),11,13(28),15,17,19(27),22,25-dodecaene-3,16,24-triol
  参考文献：
  名称：

  Synthesis of macrocyclic bisbibenzyl derivatives and their anticancer effects as anti-tubulin agents

  摘要：

  Based on the core skeleton of the total synthesized bisbibenzyl marchantin C, riccardin D and plagiochin E, a series of brominated and aminomethylated derivatives of above three bisbibenzyls have been synthesized and their cytotoxic activity against KB, MCF-7 and PC3 cell lines has been preliminary evaluated. The bio-test results revealed that the brominated derivatives 21, 22, 24, 25 and 28 exhibited excellent antiproliferative activity, with IC50 value lower than their parent compounds. As a most potent microtubule depolymerization agent, compound 28 was found to arrest cells at the G(2)/M phase of the cell cycle as determined by the flow cytometry assay in PC3 cell line. The remarkable biological profile and novel structure of these bisbibenzyl derivatives make them possible as promising candidates for clinical development as chemotherapeutic agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.004
• 作为产物：
  描述：

  间甲氧基苯甲醇 在 sodium bromate 、 对甲苯磺酸 、 sodium hydrogensulfite 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 17.5h， 生成 2-(4-bromo-3-methoxy-benzyloxy)-tetrahydro-pyran
  参考文献：
  名称：

  Syntheses of macrocyclic bisbibenzyls on solid support

  摘要：

  We describe a route for the polymer supported total synthesis of the cyclic bisbibenzyls of the isoplagiochin type found in liverworts. TentaGel (R) resins were used as solid support for a sequence involving Suzuki, Wittig and hydrogenation protocols. The polymer linked intermediates could be characterized by HR-MAS NMR. This route is to be extended to the synthesis of small libraries of differently halogenated derivatives. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.048

文献信息

• Synthesis of riccardin D derivatives as potent antimicrobial agents
  作者：Bin Sun、Ming Zhang、Ying Li、Qing-wen Hu、Hong-bo Zheng、Wen-qiang Chang、Hong-xiang Lou

  DOI：10.1016/j.bmcl.2016.06.006

  日期：2016.8

  We describe the synthesis and biological evaluation of riccardin D derivatives, a novel class of antimicrobial molecules. Structural diversification of these derivatives was achieved by introducing hydroxy, methoxy, and bromine into the aromatic rings of riccardin D. The antimicrobial evaluation of these compounds was performed as in vitro assays against clinically isolated bacteria and fungi. The

  我们描述了蓖麻素D衍生物，一类新型的抗菌分子的合成和生物学评估。这些衍生物的结构多样化是通过将羟基，甲氧基和溴引入蓖麻毒素D的芳环中实现的。这些化合物的抗微生物性评估是针对临床分离出的细菌和真菌的体外测定方法。将溴原子引入蓖麻毒素D的芳烃B中导致了几种强活性抗菌化合物，对于金黄色葡萄球菌（对甲氧西林敏感和耐药的菌株）的MIC值为0.5至4μg/ mL 。抗真菌测试发现化合物34是最有效的分子，对白色念珠菌的MIC值为2μg/ mL。最初的生物学评估表明，这些新型分子作为潜在的抗菌剂值得进一步研究。
• Synthesis of macrocyclic bisbibenzyl derivatives and their anticancer effects as anti-tubulin agents
  作者：Juan Jiang、Bin Sun、Yan-yan Wang、Min Cui、Li Zhang、Chang-zhi Cui、Yan-feng Wang、Xi-gong Liu、Hong-xiang Lou

  DOI：10.1016/j.bmc.2012.02.004

  日期：2012.4

  Based on the core skeleton of the total synthesized bisbibenzyl marchantin C, riccardin D and plagiochin E, a series of brominated and aminomethylated derivatives of above three bisbibenzyls have been synthesized and their cytotoxic activity against KB, MCF-7 and PC3 cell lines has been preliminary evaluated. The bio-test results revealed that the brominated derivatives 21, 22, 24, 25 and 28 exhibited excellent antiproliferative activity, with IC50 value lower than their parent compounds. As a most potent microtubule depolymerization agent, compound 28 was found to arrest cells at the G(2)/M phase of the cell cycle as determined by the flow cytometry assay in PC3 cell line. The remarkable biological profile and novel structure of these bisbibenzyl derivatives make them possible as promising candidates for clinical development as chemotherapeutic agents. (C) 2012 Elsevier Ltd. All rights reserved.
• Syntheses of macrocyclic bisbibenzyls on solid support
  作者：Andreas Speicher、Timo Backes、Stefan Grosse

  DOI：10.1016/j.tet.2005.09.048

  日期：2005.12

  We describe a route for the polymer supported total synthesis of the cyclic bisbibenzyls of the isoplagiochin type found in liverworts. TentaGel (R) resins were used as solid support for a sequence involving Suzuki, Wittig and hydrogenation protocols. The polymer linked intermediates could be characterized by HR-MAS NMR. This route is to be extended to the synthesis of small libraries of differently halogenated derivatives. (c) 2005 Elsevier Ltd. All rights reserved.