5-bromo-8-(methoxymethoxy)-3-methyl-1-naphthalenol | 160538-97-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-bromo-8-(methoxymethoxy)-3-methyl-1-naphthalenol
• 英文别名: 5-Bromo-8-(methoxymethoxy)-3-methylnaphthalen-1-ol
• CAS: 160538-97-6
• 化学式: C₁₃H₁₃BrO₃
• 分子量: 297.148
• InChiKey: KKTIVOZHJZYCTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-8-(methoxymethoxy)-3-methyl-1-naphthalenol 在 sodium hydroxide 、 正丁基锂 、 四丁基溴化铵 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 21.0h， 生成
  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：

  N,N-二乙基-3-甲基-2-丁酰胺 、 2,4-二溴-1-(甲氧基甲氧基)苯 在 lithium cyclohexylisopropylamide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以20%的产率得到5-bromo-8-(methoxymethoxy)-3-methyl-1-naphthalenol
  参考文献：
  名称：

  Total synthesis of Michellamines A-C: Important anti-HIV agents

  摘要：

  Michellamines A-C have been prepared by total synthesis in 7 and 16 linear steps from known and commercial materials, respectively. Key steps include i) palladium(0)-mediated biaryl coupling, ii) silver oxide promoted oxidative 1-naphthol coupling to an atropisomeric mixture of cross-ring quinones (indigoids), and iii) simultaneous per-debenzylation/reductive bleaching to the central 2,2'-binaphthol.

  DOI：

  10.1016/s0040-4039(00)78487-5

文献信息

• Total synthesis of Michellamines A-C: Important anti-HIV agents
  作者：Thomas R. Hoye、Minzhang Chen、Liang Mi、Owen P. Priest

  DOI：10.1016/s0040-4039(00)78487-5

  日期：1994.11

  Michellamines A-C have been prepared by total synthesis in 7 and 16 linear steps from known and commercial materials, respectively. Key steps include i) palladium(0)-mediated biaryl coupling, ii) silver oxide promoted oxidative 1-naphthol coupling to an atropisomeric mixture of cross-ring quinones (indigoids), and iii) simultaneous per-debenzylation/reductive bleaching to the central 2,2'-binaphthol.
• Synthesis of both axially chiral biaryls by cross-coupling of (arene)chromium complexes with naphthylboronic acids and subsequent axial isomerization
  作者：Takashi Watanabe、Ken Kamikawa、Motokazu Uemura

  DOI：10.1016/00404-0399(50)1354-k

  日期：1995.9

  Diastereomerically axial naphthyl(eta(6)-phenyl)Cr(CO)3 complexes were prepared by cross-coupling of (arene)chromium complexes with naphthylboronic acids and subsequent axial isomerization by refluxing of the coupling products in a higher boiling point solvent.
• 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.