(2'S)-1-benzoxy-3-<2-(benzoxymethoxy)-1-propyl>-5-bromo-2,6,8-trimethoxynaphthalene | 159147-22-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2'S)-1-benzoxy-3-<2-(benzoxymethoxy)-1-propyl>-5-bromo-2,6,8-trimethoxynaphthalene
• 英文别名: 5-bromo-2,6,8-trimethoxy-1-phenylmethoxy-3-[(2S)-2-(phenylmethoxymethoxy)propyl]naphthalene
• CAS: 159147-22-5
• 化学式: C₃₁H₃₃BrO₆
• 分子量: 581.503
• InChiKey: HGXGWHOBBMLKAR-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2'S)-1-benzoxy-3-<2-(benzoxymethoxy)-1-propyl>-5-bromo-2,6,8-trimethoxynaphthalene 在 palladium on activated charcoal sodium hydroxide 、 正丁基锂 、 四甲基乙二胺 、 氢气 、 氧气 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 4.0h， 生成 (2'S,S_a,2''S)-1,12-bis(2-hydroxy-1-propyl)-2,4,6,7,9,11-hexamethoxy-3,10-perylenequinone
  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：

  methyl 1-benzoxy-2,6,8-trimethoxynaphthalene-3-carboxylate 在 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (2'S)-1-benzoxy-3-<2-(benzoxymethoxy)-1-propyl>-5-bromo-2,6,8-trimethoxynaphthalene
  参考文献：
  名称：

  Atropdiastereoselective Total Synthesis of Phleichrome and the Protein Kinase C Inhibitor Calphostin A

  摘要：

  DOI：

  10.1021/ja00098a043

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.
• Atropdiastereoselective Total Synthesis of Phleichrome and the Protein Kinase C Inhibitor Calphostin A
  作者：Robert S. Coleman、Eugene B. Grant

  DOI：10.1021/ja00098a043

  日期：1994.9