1,8-bis(N,N'-dimethyl-ethyleneguanidino)naphthalene | 501931-38-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,8-bis(N,N'-dimethyl-ethyleneguanidino)naphthalene
• 英文别名: N,N'-bis(1,3-dimethyl-2-imidazolidinylidene)-1,8-naphthalenediamine；N-[8-[(1,3-dimethylimidazolidin-2-ylidene)amino]naphthalen-1-yl]-1,3-dimethylimidazolidin-2-imine
• CAS: 501931-38-0
• 化学式: C₂₀H₂₆N₆
• 分子量: 350.467
• InChiKey: IXKPXWWDTIXSTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  37.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,8-bis(N,N'-dimethyl-ethyleneguanidino)naphthalene 在 ammonium hexafluorophosphate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以96%的产率得到1,8-bis(N,N'-dimethyl-ethyleneguanidinio)naphthalene hexafluorophosphate
  参考文献：
  名称：

  1,8-Bis(dimethylethyleneguanidino)naphthalene:  Tailoring the Basicity of Bisguanidine “Proton Sponges” by Experiment and Theory

  摘要：

  1,8-Bis(dimethylethyleneguanidino)naphthalene (DMEGN), the second example of a peralkyl guanidine "proton sponge" based on the 1,8-naphthalene backbone, was prepared and fully characterized. The crystal structure analysis of monoprotonated DMEGN reveals an unsymmetrical intramolecular hydrogen bridge. A decrease in the basicity with respect to the noncyclic parent 1,8-bis(tetramethylguanidino)naphthalene was found. Nevertheless, a new proton sponge provides a new crossbar in the ladder of highly basic neutral organic compounds. A detailed theoretical study of DMEGN and related cyclic guanidines explains this surprising experimental result. Homodesmotic reactions reveal that the intramolecular hydrogen bond contributes effectively 10 kcal/mol to proton affinity of DMEGN.

  DOI：

  10.1021/jo034906+
• 作为产物：
  描述：

  1,3-二甲基-2-咪唑啉酮 在 三乙胺 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 17.0h， 生成 1,8-bis(N,N'-dimethyl-ethyleneguanidino)naphthalene
  参考文献：
  名称：

  1,8-Bis(dimethylethyleneguanidino)naphthalene:  Tailoring the Basicity of Bisguanidine “Proton Sponges” by Experiment and Theory

  摘要：

  1,8-Bis(dimethylethyleneguanidino)naphthalene (DMEGN), the second example of a peralkyl guanidine "proton sponge" based on the 1,8-naphthalene backbone, was prepared and fully characterized. The crystal structure analysis of monoprotonated DMEGN reveals an unsymmetrical intramolecular hydrogen bridge. A decrease in the basicity with respect to the noncyclic parent 1,8-bis(tetramethylguanidino)naphthalene was found. Nevertheless, a new proton sponge provides a new crossbar in the ladder of highly basic neutral organic compounds. A detailed theoretical study of DMEGN and related cyclic guanidines explains this surprising experimental result. Homodesmotic reactions reveal that the intramolecular hydrogen bond contributes effectively 10 kcal/mol to proton affinity of DMEGN.

  DOI：

  10.1021/jo034906+

文献信息

• Composition de défrisage des cheveux comprenant au moins une multiguanidine hors hydroxyde
  申请人：L'ORÉAL

  公开号：EP1723946A1

  公开（公告）日：2006-11-22

  L'invention a pour objet une composition cosmétique de défrisage des fibres kératiniques prête à l'emploi, le milieu cosmétiquement acceptable, contenant, en tant qu'agent actif de défrisage, une multiguanidine n'appartenant pas à la famille des hydroxydes. Elle vise également un kit contenant des compartiments à mettre en contact pour former la composition prête à l'emploi, ainsi qu'un procédé mettant en oeuvre cette composition.

  本发明的目的是一种用于拉直角蛋白纤维的即用型化妆品组合物，该化妆品可接受介质含有一种不属于氢氧化物家族的多胍作为活性拉直剂。本发明还包括一种含有可接触形成即用组合物的隔室的试剂盒，以及使用这种组合物的工艺。
• Hair shaping composition comprising at least one polyguanidine other than hydroxide
  申请人：Malle Gerard

  公开号：US20060269498A1

  公开（公告）日：2006-11-30

  Disclosed herein is a ready-to-use cosmetic composition for shaping keratin fibers, comprising, in a cosmetically acceptable medium, as active agent for shaping, a polyguanidine not belonging to the hydroxide family. Also disclosed herein is a kit comprising at least two compartments to be brought into contact to form the ready-to-use composition. Further disclosed herein is a method for shaping keratin fibers comprising applying this composition to the keratin fibers.
• 1,8-Bis(dimethylethyleneguanidino)naphthalene:  Tailoring the Basicity of Bisguanidine “Proton Sponges” by Experiment and Theory
  作者：Volker Raab、Klaus Harms、Jörg Sundermeyer、Borislav Kovačević、Zvonimir B. Maksić

  DOI：10.1021/jo034906+

  日期：2003.11.1

  1,8-Bis(dimethylethyleneguanidino)naphthalene (DMEGN), the second example of a peralkyl guanidine "proton sponge" based on the 1,8-naphthalene backbone, was prepared and fully characterized. The crystal structure analysis of monoprotonated DMEGN reveals an unsymmetrical intramolecular hydrogen bridge. A decrease in the basicity with respect to the noncyclic parent 1,8-bis(tetramethylguanidino)naphthalene was found. Nevertheless, a new proton sponge provides a new crossbar in the ladder of highly basic neutral organic compounds. A detailed theoretical study of DMEGN and related cyclic guanidines explains this surprising experimental result. Homodesmotic reactions reveal that the intramolecular hydrogen bond contributes effectively 10 kcal/mol to proton affinity of DMEGN.