1-benzoxy-2,6-dimethoxy-3-(hydroxymethyl)-8-(methoxymethoxy)naphthalene | 171013-05-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-benzoxy-2,6-dimethoxy-3-(hydroxymethyl)-8-(methoxymethoxy)naphthalene
• CAS: 171013-05-1
• 化学式: C₂₂H₂₄O₆
• 分子量: 384.429
• InChiKey: UDRRSLNFEKSBEB-UHFFFAOYSA-N

物化性质

• 沸点：
  565.9±50.0 °C(predicted)
• 密度：
  1.212±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-benzoxy-2,6-dimethoxy-3-(hydroxymethyl)-8-(methoxymethoxy)naphthalene 在 manganese(IV) oxide 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 21.5h， 生成 (2'R)-1-benzoxy-3-<2-(benzoxymethoxy)-1-propyl>-5-bromo-2,6-dimethoxy-4-(methoxymethoxy)naphthalene
  参考文献：
  名称：

  Synthesis of Helically Chiral Molecules: Stereoselective Total Synthesis of the Perylenequinones Phleichrome and Calphostin A

  摘要：

  The total syntheses of the perylenequinone natural products phleichrome and calphostin A are detailed. The syntheses were based on (1) the de novo construction of regiospecifically oxygenated and selectively protected naphthalene subunits, (2) the enantiospecific introduction of the stereogenic side chains using a chiral (alpha-alkoxyalkyl)-lithium reagent, and (3) a highly atropdiastereoselective Cu(I)-promoted biaryl synthesis for the stereoselective introduction of the helical axis of the calphostins. The total syntheses were achieved in 13 or 14 steps, respectively, with excellent control of absolute stereochemistry.

  DOI：

  10.1021/ja00149a012
• 作为产物：
  描述：

  3-羟基-2-甲氧基苯甲酸甲酯 在 K₂HPO₃-deactivated silica gel 、 四丁基碘化铵 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 74.5h， 生成 1-benzoxy-2,6-dimethoxy-3-(hydroxymethyl)-8-(methoxymethoxy)naphthalene
  参考文献：
  名称：

  Synthesis of Helically Chiral Molecules: Stereoselective Total Synthesis of the Perylenequinones Phleichrome and Calphostin A

  摘要：

  The total syntheses of the perylenequinone natural products phleichrome and calphostin A are detailed. The syntheses were based on (1) the de novo construction of regiospecifically oxygenated and selectively protected naphthalene subunits, (2) the enantiospecific introduction of the stereogenic side chains using a chiral (alpha-alkoxyalkyl)-lithium reagent, and (3) a highly atropdiastereoselective Cu(I)-promoted biaryl synthesis for the stereoselective introduction of the helical axis of the calphostins. The total syntheses were achieved in 13 or 14 steps, respectively, with excellent control of absolute stereochemistry.

  DOI：

  10.1021/ja00149a012

文献信息

• Synthesis of Helically Chiral Molecules: Stereoselective Total Synthesis of the Perylenequinones Phleichrome and Calphostin A
  作者：Robert S. Coleman、Eugene B. Grant

  DOI：10.1021/ja00149a012

  日期：1995.11

  The total syntheses of the perylenequinone natural products phleichrome and calphostin A are detailed. The syntheses were based on (1) the de novo construction of regiospecifically oxygenated and selectively protected naphthalene subunits, (2) the enantiospecific introduction of the stereogenic side chains using a chiral (alpha-alkoxyalkyl)-lithium reagent, and (3) a highly atropdiastereoselective Cu(I)-promoted biaryl synthesis for the stereoselective introduction of the helical axis of the calphostins. The total syntheses were achieved in 13 or 14 steps, respectively, with excellent control of absolute stereochemistry.