5-Benzyloxy-4-hydroxy-3,7-dimethoxy-naphthalene-2-carboxylic acid methyl ester | 132019-90-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-Benzyloxy-4-hydroxy-3,7-dimethoxy-naphthalene-2-carboxylic acid methyl ester
• 英文别名: Methyl 4-hydroxy-3,7-dimethoxy-5-phenylmethoxynaphthalene-2-carboxylate
• CAS: 132019-90-0
• 化学式: C₂₁H₂₀O₆
• 分子量: 368.386
• InChiKey: OZVDUAAFJXJVPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-Benzyloxy-4-hydroxy-3,7-dimethoxy-naphthalene-2-carboxylic acid methyl ester 在 硫酸 N-溴代丁二酰亚胺(NBS) 作用下， 以96%的产率得到5-Benzyloxy-8-bromo-4-hydroxy-3,7-dimethoxy-naphthalene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  An efficient synthesis of the naphthalene subunits of the protein kinase C inhibitor calphostin C

  摘要：

  An efficient synthesis of bromonaphthalenes 5b-c, which represent suitably functionalized precursors to the perylenequinone ring system characteristic of the protein kinase C inhibitor calphostin C (1), is described and was based on the Diels-Alder reaction of omicron-quinol acetate 7 with 1,1,3-trioxygenated butadienes 6a-c, followed by selective, acid-promoted elimination of R3SiOH and AcOH to directly afford naphthalenes 11a-c.

  DOI：

  10.1021/jo00004a006
• 作为产物：
  描述：

  methyl 3-(benzyloxy)-2-hydroxybenzoate 在 palladium on activated charcoal 氢气 、 4-甲基苯磺酸吡啶 、 sodium hydride 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 25.0~40.0 ℃ 、98.06 kPa 条件下， 生成 5-Benzyloxy-4-hydroxy-3,7-dimethoxy-naphthalene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  An efficient synthesis of the naphthalene subunits of the protein kinase C inhibitor calphostin C

  摘要：

  An efficient synthesis of bromonaphthalenes 5b-c, which represent suitably functionalized precursors to the perylenequinone ring system characteristic of the protein kinase C inhibitor calphostin C (1), is described and was based on the Diels-Alder reaction of omicron-quinol acetate 7 with 1,1,3-trioxygenated butadienes 6a-c, followed by selective, acid-promoted elimination of R3SiOH and AcOH to directly afford naphthalenes 11a-c.

  DOI：

  10.1021/jo00004a006

文献信息

• COLEMAN, ROBERT S.;GRANT, EUGENE B., J. ORG. CHEM., 56,(1991) N, C. 1357-1359
  作者：COLEMAN, ROBERT S.、GRANT, EUGENE B.

  DOI：——

  日期：——