5-chloro-1-(3-hydroxyphenyl)-1-pentanone | 501083-63-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-chloro-1-(3-hydroxyphenyl)-1-pentanone
• 英文别名: 5-chloro-1-(3-hydroxyphenyl)pentan-1-one
• CAS: 501083-63-2
• 化学式: C₁₁H₁₃ClO₂
• 分子量: 212.676
• InChiKey: DGMFIBDCWXYNQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-甲氧苯基)哌嗪 、 5-chloro-1-(3-hydroxyphenyl)-1-pentanone 以 乙腈 为溶剂， 以17%的产率得到1-(3-Hydroxy-phenyl)-5-[4-(2-methoxy-phenyl)-piperazin-1-yl]-pentan-1-one
  参考文献：
  名称：

  Synthesis and Structure−Affinity Relationships of 1-[ω-(4-Aryl-1-piperazinyl)alkyl]-1-aryl Ketones as 5-HT₇ Receptor Ligands

  摘要：

  Structural requirements for 5-HT7 receptor affinity and selectivity over that for the 5-HT1A receptor were studied on a series of 1-[omega-(4-aryl-1-piperazinyl)alkyl] - I-aryl ketones. The presence of a hydroxy or methoxy substituent on aryl ketone moiety, alkyl chain length, and the nature of N-1-piperazine substituent were explored. 6-[4-(3-Benzisoxazolyl)-l-piperazinyl]-1-(2-hydroxyphenyl)-1-hexanone (40) and its methoxy analogue 43 exhibited high 5-HT7 receptor affinities (K-i = 2.93 nM and 0.90 nM, respectively) and agonist properties when tested for 5-HT7 receptor-mediated relaxation of substance P-induced guinea-pig ileum contraction.

  DOI：

  10.1021/jm020994z
• 作为产物：
  描述：

  5-氯-1-(3-甲氧基苯基)-1-戊醇 在 jones reagent 、 氢溴酸 作用下， 以 水 为溶剂， 反应 4.0h， 生成 5-chloro-1-(3-hydroxyphenyl)-1-pentanone
  参考文献：
  名称：

  Synthesis and Structure−Affinity Relationships of 1-[ω-(4-Aryl-1-piperazinyl)alkyl]-1-aryl Ketones as 5-HT₇ Receptor Ligands

  摘要：

  Structural requirements for 5-HT7 receptor affinity and selectivity over that for the 5-HT1A receptor were studied on a series of 1-[omega-(4-aryl-1-piperazinyl)alkyl] - I-aryl ketones. The presence of a hydroxy or methoxy substituent on aryl ketone moiety, alkyl chain length, and the nature of N-1-piperazine substituent were explored. 6-[4-(3-Benzisoxazolyl)-l-piperazinyl]-1-(2-hydroxyphenyl)-1-hexanone (40) and its methoxy analogue 43 exhibited high 5-HT7 receptor affinities (K-i = 2.93 nM and 0.90 nM, respectively) and agonist properties when tested for 5-HT7 receptor-mediated relaxation of substance P-induced guinea-pig ileum contraction.

  DOI：

  10.1021/jm020994z

文献信息

• Synthesis and Structure−Affinity Relationships of 1-[ω-(4-Aryl-1-piperazinyl)alkyl]-1-aryl Ketones as 5-HT₇ Receptor Ligands
  作者：Roberto Perrone、Francesco Berardi、Nicola A. Colabufo、Enza Lacivita、Marcello Leopoldo、Vincenzo Tortorella

  DOI：10.1021/jm020994z

  日期：2003.2.1

  Structural requirements for 5-HT7 receptor affinity and selectivity over that for the 5-HT1A receptor were studied on a series of 1-[omega-(4-aryl-1-piperazinyl)alkyl] - I-aryl ketones. The presence of a hydroxy or methoxy substituent on aryl ketone moiety, alkyl chain length, and the nature of N-1-piperazine substituent were explored. 6-[4-(3-Benzisoxazolyl)-l-piperazinyl]-1-(2-hydroxyphenyl)-1-hexanone (40) and its methoxy analogue 43 exhibited high 5-HT7 receptor affinities (K-i = 2.93 nM and 0.90 nM, respectively) and agonist properties when tested for 5-HT7 receptor-mediated relaxation of substance P-induced guinea-pig ileum contraction.