5-bromo-8-methoxy-3-methyl-1-naphthalenol | 91571-07-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-bromo-8-methoxy-3-methyl-1-naphthalenol
• 英文别名: 5-bromo-8-methoxy-3-methyl-1-naphthol；5-Brom-8-methoxy-3-methyl-naphthol-(1)；5-Bromo-8-methoxy-3-methylnaphthalen-1-ol
• CAS: 91571-07-2
• 化学式: C₁₂H₁₁BrO₂
• 分子量: 267.122
• InChiKey: GHZUBWHAXBNJQW-UHFFFAOYSA-N

物化性质

• 熔点：
  152-153 °C
• 沸点：
  405.3±40.0 °C(Predicted)
• 密度：
  1.496±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-8-methoxy-3-methyl-1-naphthalenol 在 sodium hydroxide 、 正丁基锂 、 四丁基溴化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 (4,5-二甲氧基-7-甲基-1-萘基)硼酸
  参考文献：
  名称：

  Total Synthesis of Michellamines A−C, Korupensamines A−D, and Ancistrobrevine B

  摘要：

  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.

  DOI：

  10.1021/jo9908187
• 作为产物：
  描述：

  2,6-二甲氧基苯甲酸 在 溴 、 sodium methylate 、 magnesium 、 1,2-二溴乙烷 、 三氟乙酸酐 作用下， 以 六甲基磷酰三胺 、 溶剂黄146 、 苯 为溶剂， 反应 7.17h， 生成 5-bromo-8-methoxy-3-methyl-1-naphthalenol
  参考文献：
  名称：

  Hattori, Tetsutaro; Takeda, Ayanobu; Suzuki, Kenji, Journal of the Chemical Society. Perkin transactions I, 1998, # 22, p. 3661 - 3671

  摘要：

  DOI：

文献信息

• A Convenient Preparation of Functionalized 1,8-Dioxygenated Naphthalenes from 6-Alkoxybenzocyclobutenones
  作者：Christopher J. Bungard、Jonathan C. Morris

  DOI：10.1021/jo015887b

  日期：2002.4.1

  An alternate route for the synthesis of naphthalene building blocks 1-4 has been developed, starting from readily available 6-alkoxybenzocyclobutenones. As thermolysis of a propynylbenzocyclobutenol only provided the naphthalene in low yield, allenyl-substituted benzocyclobutenols were investigated. The desired allenic precursors were prepared by a two-step procedure, which involved hydroxyl-directed

  从容易获得的6-烷氧基苯并环丁烯酮开始，已经开发了另一种合成萘结构单元1-4的途径。由于丙炔基苯并环丁烯醇的热解仅以低产率提供萘，因此研究了烯丙基取代的苯并环丁烯醇。所需的烯丙基前体是通过两步程序制备的，该程序包括通过羟基氧化直接还原由将硫代炔丙基氯加至苯并环丁烯酮而制得的氯炔丙基苯并环丁烯醇。烯丙醇的热解以良好的收率得到了所需的萘。
• 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 the antimalarial naphthylisoquinoline alkaloid 5-epi-4′-O-demethylancistrobertsonine C by asymmetric Suzuki cross-coupling
  作者：Gerhard Bringmann、Stefan Rüdenauer、Torsten Bruhn、Lauren Benson、Reto Brun

  DOI：10.1016/j.tet.2008.03.087

  日期：2008.6

  , 1b, is described. The key step of the synthesis is the construction of the rotationally hindered and thus stereogenic biaryl axis, which was built up by a Suzuki reaction. The use of chiral ligands in the palladium-catalyzed cross-coupling permitted to increase the low internal asymmetric induction up to a diastereomeric ratio of 74:26. The assignment of the axial configurations of the atropo-diastereomers

  的第一全合成抗疟naphthylisoquinoline生物碱5-外延-4'- ø -demethylancistrobertsonine C（1A）及其-尚未非自然-atropo非对映体，1B进行说明。合成的关键步骤是通过Suzuki反应建立旋转受阻的立体立体联芳基轴。在钯催化的交叉偶联中使用手性配体可以将低的内部不对称诱导增加至非对映体比例为74:26。阻转非对映异构体的轴向构型分配通过2D NMR实验获得，并通过量子化学CD计算得到证实。
• A Convenient Synthesis of 1-Bromo- 4,5-dimethoxy-7-methylnaphthalene, a Naphthol Derivative Useful for Construction of Naphthylisoquinoline Alkaloids
  作者：Thomas R. Hoye、Liang Mi

  DOI：10.1021/jo9713262

  日期：1997.11.1
• 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.