α,α'-bis(8-formylnaphth-1-yloxy)-p-xylene | 329735-13-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: α,α'-bis(8-formylnaphth-1-yloxy)-p-xylene
• 英文别名: 8-[[4-[(8-Formylnaphthalen-1-yl)oxymethyl]phenyl]methoxy]naphthalene-1-carbaldehyde
• CAS: 329735-13-9
• 化学式: C₃₀H₂₂O₄
• 分子量: 446.502
• InChiKey: LNDWPVRFYNUMLG-UHFFFAOYSA-N

物化性质

• 沸点：
  685.4±45.0 °C(Predicted)
• 密度：
  1.274±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  α,α'-bis(8-formylnaphth-1-yloxy)-p-xylene 在 三氟化硼乙醚 、 zinc diacetate 作用下， 以 二氯甲烷 、 丙酸 为溶剂， 反应 18.75h， 生成
  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 、 pyridinium chloroformate 、 四丁基碘化铵 、 potassium carbonate 作用下， 以 二氯甲烷 、 二乙二醇二甲醚 、 丁酮 为溶剂， 反应 29.5h， 生成 α,α'-bis(8-formylnaphth-1-yloxy)-p-xylene
  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

• Controlled scrambling in porphyrin synthesis—selective synthesis of 5,10-disubstituted porphyrins
  作者：Andrew N Cammidge、Orhan Öztürk

  DOI：10.1016/s0040-4039(00)01965-1

  日期：2001.1

  Condensation of phenyldipyrromethane with bisnaphthaldehyde 3 leads to unexpected formation of the scrambled 5,10-bridged porphyrin 5; this unprecedented selectivity suggests that an alternative scrambling mechanism to dipyrromethane acidolysis is operating. (C) 2000 Elsevier Science Ltd. All rights reserved.
• 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.