Methyl 5-(benzyloxy)-8-bromo-1,4,7-trimethoxy-6-methylnaphth-3-oate | 165258-08-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Methyl 5-(benzyloxy)-8-bromo-1,4,7-trimethoxy-6-methylnaphth-3-oate
• 英文别名: Methyl 5-bromo-1,4,6-trimethoxy-7-methyl-8-phenylmethoxynaphthalene-2-carboxylate
• CAS: 165258-08-2
• 化学式: C₂₃H₂₃BrO₆
• 分子量: 475.336
• InChiKey: YNLXSYSCHCDCEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 5-(benzyloxy)-8-bromo-1,4,7-trimethoxy-6-methylnaphth-3-oate 在 palladium on activated charcoal 吡啶 、 lithium hydroxide 、 正丁基锂 、 ammonium cerium(IV) nitrate 、 air 、 叠氮磷酸二苯酯 、 氢气 、 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 39.83h， 生成 8-<(4'S,2'E)-5'-(tert-Butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-5-hydroxy-7-methoxy-6-methyl-3-carbonyl>amino>-1,4-naphthoquinone
  参考文献：
  名称：

  Synthesis of the Naphthoquinone Nucleus of Awamycin

  摘要：

  A synthesis of ketone 4, corresponding to the fully elaborated naphthoquinone nucleus of awamycin, is described. The synthesis involves the Diels-Alder reaction between diene 8 and quinone 9 to construct naphthoquinone 10, the coupling of bromide 15 and an ansa chain surrogate 17 via an aryllithium intermediate, and a late stage 1,4-addition of NaSMe to naphthoquinone 23 to afford the ketone 4.

  DOI：

  10.1021/jo00119a018
• 作为产物：
  描述：

  5-(Benzyloxy)-1,4,7-trimethoxy-6-methyl-3-naphthoic acid 在 硫酸 N-溴代丁二酰亚胺(NBS) 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 8.0h， 生成 Methyl 5-(benzyloxy)-8-bromo-1,4,7-trimethoxy-6-methylnaphth-3-oate
  参考文献：
  名称：

  Synthesis of the Naphthoquinone Nucleus of Awamycin

  摘要：

  A synthesis of ketone 4, corresponding to the fully elaborated naphthoquinone nucleus of awamycin, is described. The synthesis involves the Diels-Alder reaction between diene 8 and quinone 9 to construct naphthoquinone 10, the coupling of bromide 15 and an ansa chain surrogate 17 via an aryllithium intermediate, and a late stage 1,4-addition of NaSMe to naphthoquinone 23 to afford the ketone 4.

  DOI：

  10.1021/jo00119a018

文献信息

• Synthesis of the Naphthoquinone Nucleus of Awamycin
  作者：William R. Roush、D. Scott Coffey

  DOI：10.1021/jo00119a018

  日期：1995.7

  A synthesis of ketone 4, corresponding to the fully elaborated naphthoquinone nucleus of awamycin, is described. The synthesis involves the Diels-Alder reaction between diene 8 and quinone 9 to construct naphthoquinone 10, the coupling of bromide 15 and an ansa chain surrogate 17 via an aryllithium intermediate, and a late stage 1,4-addition of NaSMe to naphthoquinone 23 to afford the ketone 4.