5-(Benzyloxy)-3-bromo-7-methoxy-6-methyl-1,4-naphthoquinone | 165258-04-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-(Benzyloxy)-3-bromo-7-methoxy-6-methyl-1,4-naphthoquinone
• 英文别名: 2-Bromo-6-methoxy-7-methyl-8-phenylmethoxynaphthalene-1,4-dione
• CAS: 165258-04-8
• 化学式: C₁₉H₁₅BrO₄
• 分子量: 387.23
• InChiKey: SPXADYMYOOIMBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(Benzyloxy)-3-bromo-7-methoxy-6-methyl-1,4-naphthoquinone 在 四丁基溴化铵 氢氧化钾 、 sodium dithionite 、 叔丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 11.75h， 生成 5-(Benzyloxy)-1,4,7-trimethoxy-6-methyl-3-naphthoic acid
  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：

  溴甲苯 、 3-Bromo-5-hydroxy-7-methoxy-6-methyl-1,4-naphthoquinone 在 silver(l) oxide 作用下， 以 氯仿 为溶剂， 反应 6.0h， 以81%的产率得到5-(Benzyloxy)-3-bromo-7-methoxy-6-methyl-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

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.