N2,N2,N4,N4,8-pentamethylquinoline-2,4,5-triamine | 1392408-76-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N2,N2,N4,N4,8-pentamethylquinoline-2,4,5-triamine
• 英文别名: 5-amino-2,4-bis(dimethylamino)-8-methylquinoline
• CAS: 1392408-76-2
• 化学式: C₁₄H₂₀N₄
• 分子量: 244.34
• InChiKey: XNEYXYRLDNDHDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  45.39
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N2,N2,N4,N4,8-pentamethylquinoline-2,4,5-triamine 在 sodium carbonate decahydrate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 96.0h， 生成 2,4,5-tris(dimethylamino)-8-methylquinolinium monopicrate
  参考文献：
  名称：

  4,5-Bis(dimethylamino)quinolines: Proton Sponge versus Azine Behavior

  摘要：

  Two first representatives, 5 and 6, of the still unknown 4,5-bis(dimethylamino)quinoline have been synthesized and studied. While the former, being protonated either at the peri-NMe2 groups or at the ring nitrogen, has been shown to display properties of both a proton sponge and azine, its counterpart 6 behaves exclusively as azine giving only a quinolinium salt.

  DOI：

  10.1021/ol301777s
• 作为产物：
  描述：

  邻甲苯胺 在 硫酸 、 水 、 硝酸 、 铁粉 、 溶剂黄146 、 三氯氧磷 作用下， 以 乙醇 、 正丁醇 为溶剂， 反应 115.0h， 生成 N2,N2,N4,N4,8-pentamethylquinoline-2,4,5-triamine
  参考文献：
  名称：

  4,5-Bis(dimethylamino)quinolines: Proton Sponge versus Azine Behavior

  摘要：

  Two first representatives, 5 and 6, of the still unknown 4,5-bis(dimethylamino)quinoline have been synthesized and studied. While the former, being protonated either at the peri-NMe2 groups or at the ring nitrogen, has been shown to display properties of both a proton sponge and azine, its counterpart 6 behaves exclusively as azine giving only a quinolinium salt.

  DOI：

  10.1021/ol301777s

文献信息

• Nucleophilic Substitution of Hydrogen Atom in Initially Inactivated Pyrrole Ring
  作者：Alexander F. Pozharskii、Valery A. Ozeryanskii、Olga V. Dyablo、Olga G. Pogosova、Gennady S. Borodkin、Aleksander Filarowski

  DOI：10.1021/acs.orglett.8b04098

  日期：2019.4.5

  7-dialkyl-7H-pyrrolo[1,2-a]perimidine-7-ium tetrafluoroborates 5 and 7, respectively. The reaction proceeds in a highly selective manner and represents the first case of nucleophilic substitution of hydrogen in the initially inactivated pyrrole ring. The scope and limitations of the transformation, apparently operating due to the joint action of the “proximity effect” and proton catalysis, are outlined.

  已经发现1-二烷基氨基-8-（吡咯基-1）萘1和6在环境条件下用等摩尔量的HBF 4处理后，产生1-二烷基铵盐，其被转化为7,7-二烷基-7。H-吡咯并[1,2 - a ] perimidine-7-四氟硼酸盐5和7。该反应以高度选择性的方式进行，代表了最初失活的吡咯环中氢的亲核取代的第一种情况。概述了由于“邻近效应”和质子催化的共同作用而明显起作用的转变的范围和局限性。
• Synthesis of 4,5-Bis(Dimethylamino)Quinolines and the Dual Direction of their Protonation
  作者：E. A. Shmoilova、O. V. Dyablo、A. F. Pozharskii

  DOI：10.1007/s10593-013-1380-4

  日期：2013.12

  A study on the synthesis of derivatives of 4,5-bis(dimethylamino)quinoline, which is a quinoline analog of 1,8-bis(dimethylamino)naphthalene (also known by its trade name Proton Sponge) was carried out. The first two representatives of this series were obtained. Depending on the aggregate state, solvent, and structural features, these compounds may be protonated either at the quinoline heteroatom or peri-NMe2 groups.
• 4,5-Bis(dimethylamino)quinolines: Proton Sponge versus Azine Behavior
  作者：Olga V. Dyablo、Elena A. Shmoilova、Alexander F. Pozharskii、Valery A. Ozeryanskii、Oleg N. Burov、Zoya A. Starikova

  DOI：10.1021/ol301777s

  日期：2012.8.17

  Two first representatives, 5 and 6, of the still unknown 4,5-bis(dimethylamino)quinoline have been synthesized and studied. While the former, being protonated either at the peri-NMe2 groups or at the ring nitrogen, has been shown to display properties of both a proton sponge and azine, its counterpart 6 behaves exclusively as azine giving only a quinolinium salt.