4-(3-Phenoxypropyl)pyridine | 112945-01-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(3-Phenoxypropyl)pyridine
• CAS: 112945-01-4
• 化学式: C₁₄H₁₅NO
• 分子量: 213.279
• InChiKey: TYMHXGLDRUMFJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(3-Phenoxypropyl)pyridine 在 氢溴酸 作用下， 生成 4-(3-溴丙基)吡啶氢溴酸
  参考文献：
  名称：

  Psychotropic agents: synthesis and antipsychotic activity of substituted .beta.-carbolines

  摘要：

  A series of novel substituted beta-carbolines was synthesized and tested for potential antipsychotic activity. Several compounds displayed moderate antipsychotic activity in vitro and in vivo as determined by relevant receptor binding assays and behavioral tests. The effect of substituents on antipsychotic activity was examined. The beta-carbolines 10 and 19 containing 2-(2-pyridinyl)ethyl and 2-(2-quinolinyl)ethyl side chains were the most potent analogues, blocking discrete trial conditioned avoidance responding in rats with AB50's of 23 and 10 mg/kg, respectively. Both showed moderate activity at the D2 receptor sites, but they lacked oral activity. In contrast, the beta-carboline 13 containing the 4-(4-pyridinyl)butyl side chain exhibited oral activity in the discrete trial conditioned avoidance screen with an AB50 of 31 mg/kg. Most compounds did not antagonize apomorphine-induced stereotyped behavior, which is indicative of low potential for extrapyramidal side effect (EPS) liability.

  DOI：

  10.1021/jm00389a022
• 作为产物：
  描述：

  4-吡啶丙醇 、 甲磺酸苯酯 在 sodium t-butanolate 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以67%的产率得到4-(3-Phenoxypropyl)pyridine
  参考文献：
  名称：

  Synthesis of Aryl Ethers via a Sulfonyl Transfer Reaction

  摘要：

  A general synthesis of aryl ethers from primary and secondary alcohols and aryl mesylates is presented. The reaction proceeds via a sulfonyl-transfer mechanism. In this paper, we compare the sulfonyl transfer reaction to Mitsunobu ether formation. The reaction can be employed in a multistep synthesis where the aryl mesylate is used as a phenol protecting group and then as an activating group for ether formation. This protecting/activating group strategy is demonstrated using raloxifene as the target.

  DOI：

  10.1021/ol301615z

文献信息

• Synthesis of Aryl Ethers via a Sulfonyl Transfer Reaction
  作者：Neal W. Sach、Daniel T. Richter、Stephan Cripps、Michelle Tran-Dubé、Huichun Zhu、Buwen Huang、Jean Cui、Scott C. Sutton

  DOI：10.1021/ol301615z

  日期：2012.8.3

  A general synthesis of aryl ethers from primary and secondary alcohols and aryl mesylates is presented. The reaction proceeds via a sulfonyl-transfer mechanism. In this paper, we compare the sulfonyl transfer reaction to Mitsunobu ether formation. The reaction can be employed in a multistep synthesis where the aryl mesylate is used as a phenol protecting group and then as an activating group for ether formation. This protecting/activating group strategy is demonstrated using raloxifene as the target.
• Psychotropic agents: synthesis and antipsychotic activity of substituted .beta.-carbolines
  作者：Magid Abou-Gharbia、Usha R. Patel、John A. Moyer、Eric A. Muth

  DOI：10.1021/jm00389a022

  日期：1987.6

  A series of novel substituted beta-carbolines was synthesized and tested for potential antipsychotic activity. Several compounds displayed moderate antipsychotic activity in vitro and in vivo as determined by relevant receptor binding assays and behavioral tests. The effect of substituents on antipsychotic activity was examined. The beta-carbolines 10 and 19 containing 2-(2-pyridinyl)ethyl and 2-(2-quinolinyl)ethyl side chains were the most potent analogues, blocking discrete trial conditioned avoidance responding in rats with AB50's of 23 and 10 mg/kg, respectively. Both showed moderate activity at the D2 receptor sites, but they lacked oral activity. In contrast, the beta-carboline 13 containing the 4-(4-pyridinyl)butyl side chain exhibited oral activity in the discrete trial conditioned avoidance screen with an AB50 of 31 mg/kg. Most compounds did not antagonize apomorphine-induced stereotyped behavior, which is indicative of low potential for extrapyramidal side effect (EPS) liability.