Methyl 1-hydroxy-3-methyl-6-phenylmethoxynaphthalene-2-carboxylate | 444716-44-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Methyl 1-hydroxy-3-methyl-6-phenylmethoxynaphthalene-2-carboxylate
• CAS: 444716-44-3
• 化学式: C₂₀H₁₈O₄
• 分子量: 322.361
• InChiKey: URARJIQJCOXQBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 1-hydroxy-3-methyl-6-phenylmethoxynaphthalene-2-carboxylate 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 6-Hydroxy-1-methoxy-3-methyl-naphthalene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Regiospecific Synthesis of a Benanomicinone/Pradimicinone Analogue

  摘要：

  Condensation of a phenylsulfinyl naphthoate with an ortho-quinone monoketal has been used to accomplish a total synthesis of a benanomicinone/pradimicinone analogue.

  DOI：

  10.1021/ol026106b
• 作为产物：
  描述：

  4-苯甲氧基苯甲酸 在 dipotassium hydrogenphosphate 、 palladium diacetate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 29.0h， 生成 Methyl 1-hydroxy-3-methyl-6-phenylmethoxynaphthalene-2-carboxylate
  参考文献：
  名称：

  Deleterious effect of 7-methyl group on glycosylation of 2-naphthols

  摘要：

  C-Glycosylations of several 2-naphthols with different glycosyl donors have been investigated in the pursuit of the total synthesis of mayamycin (I). While glycosylations of the parent 2-naphthol are readily achievable, those of 5-methoxy-7-methyl-2-naphthol (6) embodying the target are ineffective under different Lewis acidic conditions. The inefficiency of the glycosylation of 6 has been attributed to the steric effect exerted by C7 methyl group, which was corroborated by glycosylation studies of different 2-naphthols. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.06.045

文献信息

• Deleterious effect of 7-methyl group on glycosylation of 2-naphthols
  作者：Prithiba Mitra、Subhajit Mandal、Soumen Chakraborty、Dipakranjan Mal

  DOI：10.1016/j.tet.2015.06.045

  日期：2015.8

  C-Glycosylations of several 2-naphthols with different glycosyl donors have been investigated in the pursuit of the total synthesis of mayamycin (I). While glycosylations of the parent 2-naphthol are readily achievable, those of 5-methoxy-7-methyl-2-naphthol (6) embodying the target are ineffective under different Lewis acidic conditions. The inefficiency of the glycosylation of 6 has been attributed to the steric effect exerted by C7 methyl group, which was corroborated by glycosylation studies of different 2-naphthols. (C) 2015 Elsevier Ltd. All rights reserved.
• Regiospecific Synthesis of a Benanomicinone/Pradimicinone Analogue
  作者：Frank M. Hauser、Hongbiao Liao、Yuanqiang Sun

  DOI：10.1021/ol026106b

  日期：2002.6.1

  Condensation of a phenylsulfinyl naphthoate with an ortho-quinone monoketal has been used to accomplish a total synthesis of a benanomicinone/pradimicinone analogue.