2-[[8-[[4-[[8-[bis(1H-pyrrol-2-yl)methyl]naphthalen-1-yl]oxymethyl]phenyl]methoxy]naphthalen-1-yl]-(1H-pyrrol-2-yl)methyl]-1H-pyrrole | 329735-15-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-[[8-[[4-[[8-[bis(1H-pyrrol-2-yl)methyl]naphthalen-1-yl]oxymethyl]phenyl]methoxy]naphthalen-1-yl]-(1H-pyrrol-2-yl)methyl]-1H-pyrrole
• CAS: 329735-15-1
• 化学式: C₄₆H₃₈N₄O₂
• 分子量: 678.833
• InChiKey: AVEWXTQSWRWWSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  52
• 可旋转键数：
  12
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  81.6
• 氢给体数：
  4
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  五氟苯甲醛 、 2-[[8-[[4-[[8-[bis(1H-pyrrol-2-yl)methyl]naphthalen-1-yl]oxymethyl]phenyl]methoxy]naphthalen-1-yl]-(1H-pyrrol-2-yl)methyl]-1H-pyrrole 在 zinc diacetate 、 氧气 作用下， 以 二氯甲烷 、 丙酸 为溶剂， 反应 16.0h， 以25%的产率得到
  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：

  8-羟基-1-萘甲醛 生成 2-[[8-[[4-[[8-[bis(1H-pyrrol-2-yl)methyl]naphthalen-1-yl]oxymethyl]phenyl]methoxy]naphthalen-1-yl]-(1H-pyrrol-2-yl)methyl]-1H-pyrrole
  参考文献：
  名称：

  Controlled scrambling in porphyrin synthesis—selective synthesis of 5,10-disubstituted porphyrins

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)01965-1

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.
• 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.