8-(hydroxymethyl)naphth-1-yl hexyl ether | 476646-66-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-(hydroxymethyl)naphth-1-yl hexyl ether
• 英文别名: (8-Hexoxynaphthalen-1-yl)methanol
• CAS: 476646-66-9
• 化学式: C₁₇H₂₂O₂
• 分子量: 258.36
• InChiKey: BNYMXISYMHNHDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-(hydroxymethyl)naphth-1-yl hexyl ether 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以85%的产率得到8-hexyloxy-1-naphthaldehyde
  参考文献：
  名称：

  Selective Synthesis of meso-Naphthylporphyrins

  摘要：

  A series of novel meso-(8-substituted naphth-1-yl)porphyrins has been synthesized creating derivatives with a tight recognition environment above the porphyrin plane. The selective synthesis of single atropisomers is discussed. Condensation of bisnaphthaldehyde 12 with phenyldipyrromethane unexpectedly led to selective synthesis of the alpha,alpha-5,10-bridged isomer 14. A mechanism is proposed for this unusual scrambling, and alternative syntheses of alpha,alpha-5,15-bisnaphthylporphyrins are described. Synthesis of 5,15-analogues can be achieved by employing (pentafluorophenyl)dipyrromethane or via presynthesis of a bis(dipyrromethane) derivative 22 (from bisnaphthaldehyde 12) and subsequent condensation with benzaldehyde.

  DOI：

  10.1021/jo0260488
• 作为产物：
  描述：

  2H-萘并[1,8-bc]呋喃-2-酮 在 sodium tetrahydroborate 、 四丁基碘化铵 、 potassium carbonate 作用下， 以 二乙二醇二甲醚 、 丁酮 为溶剂， 反应 4.5h， 生成 8-(hydroxymethyl)naphth-1-yl hexyl ether
  参考文献：
  名称：

  Selective Synthesis of meso-Naphthylporphyrins

  摘要：

  A series of novel meso-(8-substituted naphth-1-yl)porphyrins has been synthesized creating derivatives with a tight recognition environment above the porphyrin plane. The selective synthesis of single atropisomers is discussed. Condensation of bisnaphthaldehyde 12 with phenyldipyrromethane unexpectedly led to selective synthesis of the alpha,alpha-5,10-bridged isomer 14. A mechanism is proposed for this unusual scrambling, and alternative syntheses of alpha,alpha-5,15-bisnaphthylporphyrins are described. Synthesis of 5,15-analogues can be achieved by employing (pentafluorophenyl)dipyrromethane or via presynthesis of a bis(dipyrromethane) derivative 22 (from bisnaphthaldehyde 12) and subsequent condensation with benzaldehyde.

  DOI：

  10.1021/jo0260488

文献信息

• Selective Synthesis of <i>m</i><i>eso</i>-Naphthylporphyrins
  作者：Andrew N. Cammidge、Orhan Öztürk

  DOI：10.1021/jo0260488

  日期：2002.10.1

  A series of novel meso-(8-substituted naphth-1-yl)porphyrins has been synthesized creating derivatives with a tight recognition environment above the porphyrin plane. The selective synthesis of single atropisomers is discussed. Condensation of bisnaphthaldehyde 12 with phenyldipyrromethane unexpectedly led to selective synthesis of the alpha,alpha-5,10-bridged isomer 14. A mechanism is proposed for this unusual scrambling, and alternative syntheses of alpha,alpha-5,15-bisnaphthylporphyrins are described. Synthesis of 5,15-analogues can be achieved by employing (pentafluorophenyl)dipyrromethane or via presynthesis of a bis(dipyrromethane) derivative 22 (from bisnaphthaldehyde 12) and subsequent condensation with benzaldehyde.