N¹-(p-Chlorophenyl)-N⁵-n-propylbiguanide | 49871-96-7

• 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: N¹-(p-Chlorophenyl)-N⁵-n-propylbiguanide
• 英文别名: 1-(4-chloro-phenyl)-5-propyl-biguanide；1-(4-Chlor-phenyl)-5-propyl-biguanid；N¹-p-Chlorphenyl-N⁵-n-propylbiguanid；Paludrin；1-(4-Chlorophenyl)-4-propyl-biguanide；(1E)-1-[amino-(4-chloroanilino)methylidene]-2-propylguanidine
• CAS: 49871-96-7
• 化学式: C₁₁H₁₆ClN₅
• 分子量: 253.735
• InChiKey: CJJMEOOXAVSNFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  88.8
• 氢给体数：
  3
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-(4-chloro-phenyl)-N-cyano-triazene-1-carboxamidine 在 盐酸 、 乙醇 、 1-乙氧基乙醇 、 copper(II) sulfate 作用下， 生成 N¹-(p-Chlorophenyl)-N⁵-n-propylbiguanide
  参考文献：
  名称：

  149.合成抗疟药。第十部分。一些芳基-双胍（“-双胍”）衍生物

  摘要：

  DOI：

  10.1039/jr9460000729

文献信息

• On the anomalous sorption behaviour of chlorhexidine with poly(2-hydroxyethyl methacrylate)
  作者：B S Plaut、B J Meakin、D J G Davies

  DOI：10.1111/j.2042-7158.1980.tb12989.x

  日期：2011.4.12

  General observations of solute: plastic interactions would suggest that the sorption of the cationic preservative, chlorhexidine, with poly (2-hydroxyethyl methacrylate) (PHEMA) is not only unexpected but also atypical in its properties. The polymer and preservative were investigated independently and the sorption of PHEMA with simple solutes, namely benzoic acid, benzocaine and aniline found to exhibit conventional properties. The single exception was the uptake of small amounts of benzocaine and aniline cations at acidic pH's. In order to elucidate the sorption characteristics of chlorhexidine a series of N1-(p-chlorophenyl)-N5-alkylbiguanide acetates were synthesized. The anomalous sorption behaviour observed between PHEMA and the bis biguanide, chlorhexidine, was also found to be characteristic of these monofunctional biguanide derivatives. The extent of the interactions increased with increasing alkyl chain length (R = methyl to n-octyl), this being interpreted in terms of an interaction binding mechanism via the biguanide functional group stabilized by van der Waal's forces between the alkyl chain and the polymer backbone. Atypical sorption behaviour was observed for simple organic cations, biguanide and N1-phenylbiguanide acetate with PHEMA, a possible inference being that this is a general characteristic of all cationic sorption with PHEMA.

  关于溶质：塑料相互作用的总体观察表明，阳离子防腐剂氯己定的吸附与聚（2-羟基乙基甲基丙烯酸酯）（PHEMA）的吸附不仅是出乎意料的，而且在其性质上也是非典型的。研究了聚合物和防腐剂，发现PHEMA与简单溶质（即苯甲酸、苯佐卡因和苯胺）的吸附表现出常规性质。唯一的例外是在酸性pH下，苯佐卡因和苯胺阳离子的小量吸收。为了阐明氯己定的吸附特性，合成了一系列N1-（对氯苯基）-N5-烷基双胍醋酸盐。在PHEMA与双胍，氯己定之间的异常吸附行为也发现是这些单功能双胍衍生物的特征。随着烷基链长（R =甲基至正辛基）的增加，相互作用的程度增加，这被解释为通过双胍功能团介导的相互作用结合机制，该机制通过烷基链与聚合物主链之间的范德华力得到稳定。简单有机阳离子、双胍和N1-苯基双胍醋酸盐与PHEMA的吸附表现出非典型的吸附行为，可能的推断是这是所有阳离子与PHEMA吸附的一般特征。

• Manufacture of biguanide derivatives
  申请人：ICI LTD

  公开号：US02544827A1

  公开（公告）日：1951-03-13
• DE815344
  申请人：——

  公开号：——

  公开（公告）日：——
• DE812667
  申请人：——

  公开号：——

  公开（公告）日：——
• US7172867B2
  申请人：——

  公开号：US7172867B2

  公开（公告）日：2007-02-06