1-Piperidino-5-(4-chlorophenoxy)pentane | 108980-36-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-Piperidino-5-(4-chlorophenoxy)pentane
• 英文别名: 1-[5-(4-chloro-phenoxy)-pentyl]-piperidine；1-[5-(4-Chlor-phenoxy)-pentyl]-piperidin；1-[5-(4-Chlorophenoxy)pentyl]piperidine
• CAS: 108980-36-5
• 化学式: C₁₆H₂₄ClNO
• 分子量: 281.826
• InChiKey: CISLNJILBFCUJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Piperidino-5-(4-chlorophenoxy)pentane 在 sodium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 0.17h， 以20%的产率得到1-Piperidino-5-(4-hydroxyphenoxy)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
• 作为产物：
  描述：

  对氯苯酚 在 乙醇 、 sodium ethanolate 作用下， 生成 1-Piperidino-5-(4-chlorophenoxy)pentane
  参考文献：
  名称：

  Beasley et al., Journal of Pharmacy and Pharmacology, 1958, vol. 10, p. 47,59

  摘要：

  DOI：