1,5-Ditosyloxy-3-phenylpentan | 863-69-4

• 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: 1,5-Ditosyloxy-3-phenylpentan
• 英文别名: [5-(4-Methylphenyl)sulfonyloxy-3-phenylpentyl] 4-methylbenzenesulfonate
• CAS: 863-69-4
• 化学式: C₂₅H₂₈O₆S₂
• 分子量: 488.626
• InChiKey: NASYVYZFZDECNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,5-Ditosyloxy-3-phenylpentan 在 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 48.0h， 生成 1-[5-(4'-chlorobiphenyl-4-yloxy)-3-phenylpentyl]-3-pyridin-4-ylimidazolidin-2-one
  参考文献：
  名称：

  Design, Synthesis, and Antipicornavirus Activity of 1-[5-(4-Arylphenoxy)alkyl]-3-pyridin-4-ylimidazolidin-2-one Derivatives

  摘要：

  A series of pyridylimidazolidinone derivatives was synthesized and tested in vitro against enterovirus 71 (EV71). On the basis of compound 33 (DBPR103), introduction of a methyl group at the 2- or 3-position of the linker between the imidazolidinone and the biphenyl resulted in markedly improved antiviral activity toward EV71 with IC50 values of 5.0 nM (24b) and 9.3 nM (14a), respectively. Increasing the branched chain to propyl resulted in a progressive decrease in activity, while inserting different heteroatoms entirely rendered the compound only weakly active. The introduction of a bulky group (cyclohexyl, phenyl, or benzyl) led to loss of activity against EV71. The 4-chlorophenyl moiety in 14a was replaced with bioisosteric groups such as oxadiazole (28a-d) or tetrazole (32a,b), dramatically improving anti-EV71 activity and selectivity indices. Compounds 14a, 24b, 28b, 28d, and 32a exhibited a strong activity against lethal EV71, and no apparent cellular toxicity was observed. Three of the more potent imidazolidinone compounds, 14a, 28b, and 32b, were subjected to a large group of picornaviruses to determine their spectrum of antiviral activity.

  DOI：

  10.1021/jm050033v
• 作为产物：
  描述：

  3-苯基戊二酸 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 1,5-Ditosyloxy-3-phenylpentan
  参考文献：
  名称：

  Design, Synthesis, and Antipicornavirus Activity of 1-[5-(4-Arylphenoxy)alkyl]-3-pyridin-4-ylimidazolidin-2-one Derivatives

  摘要：

  A series of pyridylimidazolidinone derivatives was synthesized and tested in vitro against enterovirus 71 (EV71). On the basis of compound 33 (DBPR103), introduction of a methyl group at the 2- or 3-position of the linker between the imidazolidinone and the biphenyl resulted in markedly improved antiviral activity toward EV71 with IC50 values of 5.0 nM (24b) and 9.3 nM (14a), respectively. Increasing the branched chain to propyl resulted in a progressive decrease in activity, while inserting different heteroatoms entirely rendered the compound only weakly active. The introduction of a bulky group (cyclohexyl, phenyl, or benzyl) led to loss of activity against EV71. The 4-chlorophenyl moiety in 14a was replaced with bioisosteric groups such as oxadiazole (28a-d) or tetrazole (32a,b), dramatically improving anti-EV71 activity and selectivity indices. Compounds 14a, 24b, 28b, 28d, and 32a exhibited a strong activity against lethal EV71, and no apparent cellular toxicity was observed. Three of the more potent imidazolidinone compounds, 14a, 28b, and 32b, were subjected to a large group of picornaviruses to determine their spectrum of antiviral activity.

  DOI：

  10.1021/jm050033v

文献信息

• Conformational effects in compounds with 6-membered rings—X
  作者：P.J. Halfpenny、P.J. Johnson、M.J.T. Robinson、M.G. Ward

  DOI：10.1016/0040-4020(76)85189-7

  日期：1976.1

  relative kinetic and thermodynamic stereoselectivities shown in the reaction between methyl iodide and either N-methylpiperidines or thians is explained by different directions of approach to these 6-membered rings during axial attack.

  顺式和反式-3,5-二叔丁基噻烷（1和2的便捷立体定向合成）） 已经开发了。已经研究了具有不受阻碍的S原子的anantomeromer thian与甲基碘之间的反应，以及动力学（从6.5到11：1）和热力学（从1.25到2.8：1）的立体选择性范围，其中赤道S + -Me一直受到青睐，已经观察到。可以得出结论，观察到的立体选择性可以用硫在轴向位点的位阻来最好地解释，并且扭曲构象异构体对这类反应中大多数噻吩的反应性没有显着贡献。甲基碘与N-甲基哌啶或噻吩之间的反应中显示的相对动力学和热力学立体选择性之间的差异，是通过在轴向攻击过程中接近这些6元环的不同方向来解释的。
• cis- and trans-1,5-Diphenylcyclooctane
  作者：Arthur C. Cope、Robert J. Cotter

  DOI：10.1021/jo01035a005

  日期：1964.12
• PYRROLIDINE AND PIPERIDINE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY
  申请人：MERCK & CO., INC.

  公开号：EP1009405A1

  公开（公告）日：2000-06-21
• EP1009405A4
  申请人：——

  公开号：EP1009405A4

  公开（公告）日：2001-05-09
• US6166037A
  申请人：——

  公开号：US6166037A

  公开（公告）日：2000-12-26