α-Bromo-ω-(2-methoxy-4-nitrophenoxy)pentane | 100141-12-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: α-Bromo-ω-(2-methoxy-4-nitrophenoxy)pentane
• 英文别名: 5-(2-Methoxy-4-nitro-phenoxy)-pentylbromid；1-(5-Bromopentoxy)-2-methoxy-4-nitrobenzene
• CAS: 100141-12-6
• 化学式: C₁₂H₁₆BrNO₄
• mdl: MFCD19099050
• 分子量: 318.167
• InChiKey: JHDWBUFWOPTFSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  α-Bromo-ω-(2-methoxy-4-nitrophenoxy)pentane 在 镍 氢气 作用下， 以 乙醇 为溶剂， 生成 5-Acetoxy-1-(4-amino-2-methoxy-phenoxy)-pentan
  参考文献：
  名称：

  363.血吸虫病的化学疗法。第四部分 4-氨基-2-甲氧基苯酚的一些醚

  摘要：

  DOI：

  10.1039/jr9610001863
• 作为产物：
  描述：

  1,5-二溴戊烷 、 potassium 2-methoxy-4-nitrophenolate 以 丙酮 为溶剂， 反应 30.0h， 生成 α-Bromo-ω-(2-methoxy-4-nitrophenoxy)pentane
  参考文献：
  名称：

  Topologically Controlled Coulombic Interactions, a New Tool in the Developing of Novel Reactivity. Photochemical and Electrochemical Cleavage of Phenyl Alkyl Ethers

  摘要：

  The hypothesis that a specific placement of a positive charge would dramatically alter the behavior of a charged intermediate has been tested. Phenyl ethers substituted by electron-attracting groups do not undergo reductive fragmentation. However, related alpha-piperidino-omega-(4-substituted-phenoxy)-alkanes give alkyl ether photocleavage when the linker between the redox centers is short, or the usual substitution-reduction photochemistry when it is long. Mechanistic experiments suggest that the photofragmentation process operates through space intramolecular electron transfer to the triplet aromatic chromophore and that a coplanar relative orientation of the alkyl ether bond and the phenyl ring is compulsory for the photofragmentation to be observed. Configuration interaction AM1 calculations justify the described facts, indicating that the fragmentation process is only operative when a Coulombic stabilization of a sigma* intramolecular electron transfer excited state is produced. Electrochemical studies carried out with the corresponding quaternary salts (intermolecular generation of the phenyl ether radical anion) confirm the conclusions derived from the photochemical experiments.

  DOI：

  10.1021/jo00117a037

文献信息

• 34. The chemotherapy of schistosomiasis. Part V. Cholesteryl and choloyl derivatives of 4-amino-2-methoxyphenyl ethers
  作者：M. Davis

  DOI：10.1039/jr9620000178

  日期：——
• 363. The chemotherapy of schistosomiasis. Part IV. Some ethers of 4-amino-2-methoxyphenol
  作者：R. F. Collins、M. Davis

  DOI：10.1039/jr9610001863

  日期：——
• Topologically Controlled Coulombic Interactions, a New Tool in the Developing of Novel Reactivity. Photochemical and Electrochemical Cleavage of Phenyl Alkyl Ethers
  作者：Jorge Marquet、Eduard Cayon、Xavier Martin、Francisco Casado、Iluminada Gallardo、Miquel Moreno、Jose M. Lluch

  DOI：10.1021/jo00117a037

  日期：1995.6

  The hypothesis that a specific placement of a positive charge would dramatically alter the behavior of a charged intermediate has been tested. Phenyl ethers substituted by electron-attracting groups do not undergo reductive fragmentation. However, related alpha-piperidino-omega-(4-substituted-phenoxy)-alkanes give alkyl ether photocleavage when the linker between the redox centers is short, or the usual substitution-reduction photochemistry when it is long. Mechanistic experiments suggest that the photofragmentation process operates through space intramolecular electron transfer to the triplet aromatic chromophore and that a coplanar relative orientation of the alkyl ether bond and the phenyl ring is compulsory for the photofragmentation to be observed. Configuration interaction AM1 calculations justify the described facts, indicating that the fragmentation process is only operative when a Coulombic stabilization of a sigma* intramolecular electron transfer excited state is produced. Electrochemical studies carried out with the corresponding quaternary salts (intermolecular generation of the phenyl ether radical anion) confirm the conclusions derived from the photochemical experiments.