ancistrobrevine B | 146471-74-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: ancistrobrevine B
• 英文别名: (1S,3S)-5-(4,5-dimethoxy-7-methylnaphthalen-1-yl)-8-methoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-6-ol
• CAS: 146471-74-1
• 化学式: C₂₅H₂₉NO₄
• 分子量: 407.51
• InChiKey: XVHCBOXBWSMNHG-GJZGRUSLSA-N

物化性质

• 沸点：
  580.8±50.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  60
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  trans-6,8-Dimethoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline 在 palladium on activated charcoal 四(三苯基膦)钯 、 正丁基锂 、 硼酸三甲酯 、 氨 、 氢溴酸 、 氢气 、 碘 、 碳酸氢钠 、 potassium carbonate 、 silver sulfate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 溶剂黄146 、 丁酮 为溶剂， 反应 4.0h， 生成 ancistrobrevine B
  参考文献：
  名称：

  甲胺苯丙胺C和顺牛膝B的总合成

  摘要：

  首次完成了科鲁苯胺C（3）和antrotrobrevine B（4）的首次合成。描述了与萘部分的构造，四氢异喹啉单元上甲氧基的操纵以及受阻联芳基的形成有关的重要的苯炔化学。

  DOI：

  10.1016/0040-4039(96)00525-4

文献信息

• Total syntheses of korupensamine C and ancistrobrevine B
  作者：Thomas R Hoye、Liang Mi

  DOI：10.1016/0040-4039(96)00525-4

  日期：1996.4

  The first total syntheses of korupensamine C (3) and ancistrobrevine B (4) have been achieved. Important benzyne chemistry related to the construction of the naphthalene moiety, manipulation of methoxy groups on the tetrahydroisoquinoline unit, and hindered biaryl formation are described.

  首次完成了科鲁苯胺C（3）和antrotrobrevine B（4）的首次合成。描述了与萘部分的构造，四氢异喹啉单元上甲氧基的操纵以及受阻联芳基的形成有关的重要的苯炔化学。
• Total Synthesis of Michellamines A−C, Korupensamines A−D, and Ancistrobrevine B
  作者：Thomas R. Hoye、Minzhang Chen、Bac Hoang、Liang Mi、Owen P. Priest

  DOI：10.1021/jo9908187

  日期：1999.9.1

  Efficient syntheses of the title compounds have been developed. Several strategies for preparation of each of the naphthalene and tetrahydroisoquinoline (THIQ) portions were developed. Initial attempts to use benzyne plus furan cycloaddition reactions were thwarted by the unfavorable sense of the regiochemical outcome. An interesting annulation reaction of benzynes derived from 2,4-dibromophenol derivatives formed the core of the shortest naphthalene synthesis. An alternative annulation initiated by the addition of a benzylic sulfone anion to methyl crotonate led to an efficient naphthol synthesis amenable to large scale. The THIQ synthesis of Bringmann was used initially and subsequently complemented by a route whose key step involved the opening of N-tosyl-2-methylethyleneimine by a 3,5-dimethoxyphenylcuprate reagent. The results from a variety of aryl cross-coupling reactions are described. Suzuki coupling of the boronic acid derived from the naphthalene moiety with a THIQ-iodide was the most generally effective method for forming the hindered biaryl bond. The korupensamines and ancistrobrevine B were then revealed by deprotection. The oxidative coupling of several 4-aryl-1-naphthols to indigoids (cross ring naphthoquinones) with silver oxide effected the critical dimerization reaction needed to establish the michellamine skeleton. For the perbenzylated precursor, hydrogen over palladium on carbon both reductively bleached the indigoid and hydrogenolyzed the benzyl ethers and amines to release the free michellamines. The synthesis of several michellamine analogues, including ent-michellamines, is outlined. Results of anti-HIV assays are presented.