4-(4-chlorophenoxy)butanenitrile | 501941-41-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(4-chlorophenoxy)butanenitrile
• 英文别名: 4-(4-chlorophenoxy)butyronitrile；4-(4-chloro-phenoxy)-butyronitrile；4-(4-Chlor-phenoxy)-buttersaeure-nitril；4-(4-Chlor-phenoxy)-butyronitril
• CAS: 501941-41-9
• 化学式: C₁₀H₁₀ClNO
• mdl: MFCD07348582
• 分子量: 195.648
• InChiKey: PJOZPLWZTFMIOS-UHFFFAOYSA-N

物化性质

• 熔点：
  44.5-45.3 °C
• 沸点：
  324.1±17.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(4-chlorophenoxy)butanenitrile 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 异戊醇 为溶剂， 反应 16.5h， 生成 N-[4-(4-chlorophenoxy)butyl]-1H-benzimidazol-2-amine
  参考文献：
  名称：

  Synthesis and biological evaluation of new non-imidazole H3-receptor antagonists of the 2-aminobenzimidazole series

  摘要：

  A novel series of non-imidazole H-3-receptor antagonists was developed, by chemical modification of a potent lead H-3-antagonist composed by an imidazole ring connected through an alkyl spacer to a 2-aminobenzimidazole moiety (e.g., 2-[[3-[4(5)-imidazolyl]propyl]amino]benzimidazole), previously reported by our research group. We investigated whether the removal of the imidazole ring could allow retaining high affinity for the H-3-receptor, thanks to the interactions undertaken by the 2-aminobenzimidazole moiety at the binding site. The imidazole ring of the lead was replaced by a basic piperidine or by a lipophilic p-chlorophenoxy substituent, modulating the spacer length from three to eight methylene groups; moreover, the substituents were moved to the 5(6) position of the benzimidazole nucleus. Within both the 2-alkylaminobenzimidazole series and the 5(6)-alkoxy-2-amino-benzimidazole one, the greatest H-3-receptor affinity was obtained for the piperidine-substituted compounds, while the presence of the p-chlorophenoxy group resulted in a drop in affinity. The optimal chain length was different in the two series. Even if the new compounds did not reach the high receptor affinity shown by the imidazole-containing lead compound, it was possible to get good H-3-antagonist potencies with 2-aminobenzimidazoles having a tertiary amino group at appropriate distance. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.063
• 作为产物：
  描述：

  对氯苯酚 、 4-溴丁腈 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 20.0h， 以85%的产率得到4-(4-chlorophenoxy)butanenitrile
  参考文献：
  名称：

  取代苯基醚的Truce–Smiles重排†

  摘要：

  研究了分子内亲核芳族取代反应（称为Truce-Smiles重排）中底物中强电子吸收取代基对芳环活化的要求。初步的力学实验支持S N Ar机理，包括原位形成的Meisenheimer中间体的1 H和13 C NMR光谱。通常观察到重排对于具有强吸电子取代基（例如硝基，氰基和苯甲酰基官能团）的底物是成功的，但对于具有多个弱吸电子取代基（例如氯和溴官能团）的底物也是如此组。这些结果提供进一步的澄清的芳基取代基在这种类型的S的影响Ñ的Ar反应。另外，该调查还揭示了某些底物进行的一些串联环化和/或消除反应。

  DOI：

  10.1039/c5ob00812c

文献信息

• Ligand-Free, Palladium-Catalyzed Dihydrogen Generation from TMDS: Dehalogenation of Aryl Halides on Water
  作者：Anish Bhattacharjya、Piyatida Klumphu、Bruce H. Lipshutz

  DOI：10.1021/ol5037369

  日期：2015.3.6

  A mild and environmentally attractive dehalogenation of functionalized aryl halides has been developed using nanoparticles formed from PdCl2 in the presence of tetramethyldisiloxane (TMDS) on water. The active catalyst and reaction medium can be recycled. This method can also be applied to cascade reactions in a one-pot sequence.

  在水上存在四甲基二硅氧烷（TMDS）的情况下，使用由PdCl 2形成的纳米颗粒，开发了一种功能化的芳基卤化物，具有温和且对环境有吸引力的脱卤作用。活性催化剂和反应介质可以再循环。该方法也可以应用于一锅法级联反应。
• Fawcett et al., Proceedings of the Royal Society of London. Series B, Biological sciences, 1959, vol. 150, p. 95,100
  作者：Fawcett et al.

  DOI：——

  日期：——
• New Compounds. New Compounds as Plant Growth Regulators
  作者：Melvin Newman、William Fones、Mary Renoll

  DOI：10.1021/ja01195a604

  日期：1947.3
• Truce–Smiles rearrangement of substituted phenyl ethers
  作者：Joel R. Kosowan、Zemane W'Giorgis、Ravneet Grewal、Tabitha E. Wood

  DOI：10.1039/c5ob00812c

  日期：——

  ring activation by strong-electron withdrawing substituents in substrates for the intramolecular nucleophilic aromatic substitution reaction known as the Truce–Smiles rearrangement was examined. Preliminary mechanistic experiments support the SNAr mechanism, including 1H and 13C NMR spectra of a Meisenheimer intermediate formed in situ. The rearrangement was generally observed to be successful for substrates

  研究了分子内亲核芳族取代反应（称为Truce-Smiles重排）中底物中强电子吸收取代基对芳环活化的要求。初步的力学实验支持S N Ar机理，包括原位形成的Meisenheimer中间体的1 H和13 C NMR光谱。通常观察到重排对于具有强吸电子取代基（例如硝基，氰基和苯甲酰基官能团）的底物是成功的，但对于具有多个弱吸电子取代基（例如氯和溴官能团）的底物也是如此组。这些结果提供进一步的澄清的芳基取代基在这种类型的S的影响Ñ的Ar反应。另外，该调查还揭示了某些底物进行的一些串联环化和/或消除反应。
• Synthesis and biological evaluation of new non-imidazole H3-receptor antagonists of the 2-aminobenzimidazole series
  作者：Mirko Rivara、Valentina Zuliani、Giuseppe Cocconcelli、Giovanni Morini、Mara Comini、Silvia Rivara、Marco Mor、Fabrizio Bordi、Elisabetta Barocelli、Vigilio Ballabeni、Simona Bertoni、Pier Vincenzo Plazzi

  DOI：10.1016/j.bmc.2005.09.063

  日期：2006.3

  A novel series of non-imidazole H-3-receptor antagonists was developed, by chemical modification of a potent lead H-3-antagonist composed by an imidazole ring connected through an alkyl spacer to a 2-aminobenzimidazole moiety (e.g., 2-[[3-[4(5)-imidazolyl]propyl]amino]benzimidazole), previously reported by our research group. We investigated whether the removal of the imidazole ring could allow retaining high affinity for the H-3-receptor, thanks to the interactions undertaken by the 2-aminobenzimidazole moiety at the binding site. The imidazole ring of the lead was replaced by a basic piperidine or by a lipophilic p-chlorophenoxy substituent, modulating the spacer length from three to eight methylene groups; moreover, the substituents were moved to the 5(6) position of the benzimidazole nucleus. Within both the 2-alkylaminobenzimidazole series and the 5(6)-alkoxy-2-amino-benzimidazole one, the greatest H-3-receptor affinity was obtained for the piperidine-substituted compounds, while the presence of the p-chlorophenoxy group resulted in a drop in affinity. The optimal chain length was different in the two series. Even if the new compounds did not reach the high receptor affinity shown by the imidazole-containing lead compound, it was possible to get good H-3-antagonist potencies with 2-aminobenzimidazoles having a tertiary amino group at appropriate distance. (c) 2005 Elsevier Ltd. All rights reserved.