(2-benzyloxy-3-methoxybenzyl)triphenylphosphonium bromide | 1231977-84-6

• 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: (2-benzyloxy-3-methoxybenzyl)triphenylphosphonium bromide
• 英文别名: (3-Methoxy-2-phenylmethoxyphenyl)methyl-triphenylphosphanium;bromide
• CAS: 1231977-84-6
• 化学式: Br*C₃₃H₃₀O₂P
• 分子量: 569.478
• InChiKey: FHHWAFIWEYWIPT-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-benzyloxy-3-methoxybenzyl)triphenylphosphonium bromide 在 偶氮二异丁腈 、 palladium 10% on activated carbon 、 lithium methanolate 、 氢气 、 三正丁基氢锡 作用下， 以 甲烷磺酸 、 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 100.0~110.0 ℃ 、482.64 kPa 条件下， 反应 27.0h， 生成 9,10-dihydro-2,5-dimethoxyphenanthrene-1,7-diol
  参考文献：
  名称：

  Regioselective synthesis of phenanthrenes and evaluation of their anti-oxidant based anti-inflammatory potential

  摘要：

  Regioselective synthesis of 9,10-Dihydro-2,5-Dimethoxyphenanthrene-1,7-diol (1) and 9,10-Dihydro-2,7-Dimethoxyphenanthrene-1,5-diol (2) was achieved using regioselective methylation, Wittig reaction, intramolecular cyclization and hydrogenation as key steps. The synthesis was successfully completed in total of 15 steps with 3.3% overall yield in case of 1 and in total of 13 steps with 9.0% overall yield in case of 2. All compounds (1-4) showed good antioxidant and anti-inflammatory activity in in vitro assays and these activities were found to be due the presence of phenolic hydroxyl groups. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.016
• 作为产物：
  描述：

  2-苄氧基-3-甲氧基苯甲醛 在 sodium tetrahydroborate 、 三溴化磷 作用下， 以 二氯甲烷 、 异丙醇 、 甲苯 为溶剂， 反应 7.0h， 生成 (2-benzyloxy-3-methoxybenzyl)triphenylphosphonium bromide
  参考文献：
  名称：

  Regioselective synthesis of phenanthrenes and evaluation of their anti-oxidant based anti-inflammatory potential

  摘要：

  Regioselective synthesis of 9,10-Dihydro-2,5-Dimethoxyphenanthrene-1,7-diol (1) and 9,10-Dihydro-2,7-Dimethoxyphenanthrene-1,5-diol (2) was achieved using regioselective methylation, Wittig reaction, intramolecular cyclization and hydrogenation as key steps. The synthesis was successfully completed in total of 15 steps with 3.3% overall yield in case of 1 and in total of 13 steps with 9.0% overall yield in case of 2. All compounds (1-4) showed good antioxidant and anti-inflammatory activity in in vitro assays and these activities were found to be due the presence of phenolic hydroxyl groups. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.016

文献信息

• Synthesis of marchantin C, a novel microtubule inhibitor from liverworts
  作者：Andreas Speicher、Judith Holz

  DOI：10.1016/j.tetlet.2010.03.125

  日期：2010.6

  Recently, remarkable microtubule inhibitor and anti-tumor activities of the bisbibenzyl marchantin C—isolated from liverworts like Marchantia polymorpha since 1983—were found. In this Letter we describe the first and efficient total synthesis of this subtype of bisbibenzylic compounds with two biarylether connections. The structure was confirmed by the spectroscopic data which were analyzed carefully

  最近，人们发现了自1983年以来就从多形玛氏花之类的地草中分离出的双联苄基马氏素C，具有显着的微管抑制剂和抗肿瘤活性。在这封信中，我们描述了具有两个联芳基醚连接的双联二苄基化合物亚型的第一个有效的全合成方法。通过光谱数据证实了该结构，对光谱数据进行了仔细分析以排除芳烃连接和取代模式中的任何错误。