3-Piperidino-1-(2-hydroxy-4-nitrophenoxy)propane | 136616-38-1

• 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: 3-Piperidino-1-(2-hydroxy-4-nitrophenoxy)propane
• 英文别名: 5-Nitro-2-(3-piperidin-1-ylpropoxy)phenol；5-nitro-2-(3-piperidin-1-ylpropoxy)phenol
• CAS: 136616-38-1
• 化学式: C₁₄H₂₀N₂O₄
• 分子量: 280.324
• InChiKey: RAZDXAOBWJOUCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  78.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-Piperidino-3-(2-methoxy-4-nitrophenoxy)propane 在 水 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以50%的产率得到4-硝基愈创木酚
  参考文献：
  名称：

  Use of intramolecular coulombic interactions to achieve impossible reactions. Photochemical cleavage of 4-nitrophenyl ethers

  摘要：

  DOI：

  10.1021/ja00023a069

文献信息

• Use of intramolecular coulombic interactions to achieve impossible reactions. Photochemical cleavage of 4-nitrophenyl ethers
  作者：Eduard Cayon、Jorge Marquet、Jose M. Lluch、Xavier Martin

  DOI：10.1021/ja00023a069

  日期：1991.11
• 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.