2,6-bis(allylamino)pyridine | 1195970-62-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2,6-bis(allylamino)pyridine
• 英文别名: 2-N,6-N-bis(prop-2-enyl)pyridine-2,6-diamine
• CAS: 1195970-62-7
• 化学式: C₁₁H₁₅N₃
• 分子量: 189.26
• InChiKey: XQCOILOEMGZGKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  37
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-二溴吡啶 、 2,6-bis(allylamino)pyridine 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以77%的产率得到N2,N6-bis(6-bromopyridin-2-yl)-N2,N6-diallylpyridine-2,6-diamine
  参考文献：
  名称：

  Synthesis of (NH)_m(NMe)_4−m-Bridged Calix[4]pyridines and the Effect of NH Bridge on Structure and Properties

  摘要：

  The (NH)(m)(NMe)(4-m)-bridged calix[4]pyridines (m = 1-4) 19-23 were synthesized in excellent yields from deprotection of N-allyl groups of (NAllyl)(m)(NMe)(4-m)-bridged calix[4]pyridine derivatives 8 and 15-18, which were prepared in moderate yields by macrocyclic 2+2 and 1+3 coupling reactions between simple diamino- and dibromo-substituted fragments, In the solid state, (NH)(m)(NMe)(4-m)-bridged calix[4]pyridines adopted different 1,3-alternate conformations due to mainly the formation of varied conjugation systems of bridging NH units with their neighboring pyridines. In solution, all (NH)(m)(NMe)(4-m)-bridged calix[4]pyridines were very fluxional and the rates of interconversion of various conformational structures were very rapid relative to the NMR time scale, While (NH)(4)-bridged calix[4]pyridine 23 formed the strongest conjugation system, (NH)(2)(NMe)(2)-bridged calix[4]pyridine 21 acted as a selective fluorescence probe in the recognition of zinc(II) ion in solution with the dramatic enhancement of fluorescence intensity.

  DOI：

  10.1021/jo901609u
• 作为产物：
  描述：

  2,6-二溴吡啶 、 丙烯胺 在 copper(l) iodide 、 potassium carbonate 、 L-脯氨酸 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 24.0h， 以62%的产率得到2,6-bis(allylamino)pyridine
  参考文献：
  名称：

  Synthesis of (NH)_m(NMe)_4−m-Bridged Calix[4]pyridines and the Effect of NH Bridge on Structure and Properties

  摘要：

  The (NH)(m)(NMe)(4-m)-bridged calix[4]pyridines (m = 1-4) 19-23 were synthesized in excellent yields from deprotection of N-allyl groups of (NAllyl)(m)(NMe)(4-m)-bridged calix[4]pyridine derivatives 8 and 15-18, which were prepared in moderate yields by macrocyclic 2+2 and 1+3 coupling reactions between simple diamino- and dibromo-substituted fragments, In the solid state, (NH)(m)(NMe)(4-m)-bridged calix[4]pyridines adopted different 1,3-alternate conformations due to mainly the formation of varied conjugation systems of bridging NH units with their neighboring pyridines. In solution, all (NH)(m)(NMe)(4-m)-bridged calix[4]pyridines were very fluxional and the rates of interconversion of various conformational structures were very rapid relative to the NMR time scale, While (NH)(4)-bridged calix[4]pyridine 23 formed the strongest conjugation system, (NH)(2)(NMe)(2)-bridged calix[4]pyridine 21 acted as a selective fluorescence probe in the recognition of zinc(II) ion in solution with the dramatic enhancement of fluorescence intensity.

  DOI：

  10.1021/jo901609u

文献信息

• Liquid crystalline macrocyclic azacalix[4]pyridine and its complexes with the zinc ion: conformational change from the saddle to flattened shape
  作者：Shi-Xin Fa、Xiao-Fang Chen、Shuang Yang、De-Xian Wang、Liang Zhao、Er-Qiang Chen、Mei-Xiang Wang

  DOI：10.1039/c5cc01018g

  日期：——

  Substituted with four 3,4,5-tris(alkoxy)benzyl mini-dendrons, azacalix[4]pyridine (1) with the saddle-shaped core is the first liquid crystal (LC) of heteracalixaromatics. Conformational regulation of azacalix[4]pyridine by complexing with the zinc ion leads to a significant change in LC properties.

  具有马鞍形核的azacalix [4]吡啶（1）取代了四个3,4,5-三（烷氧基）苄基迷你树枝状结构，是杂芳烃的第一个液晶（LC）。通过与锌离子络合，构象调节氮杂杯[4]吡啶导致LC特性发生重大变化。
• JP2003261568A
  申请人：——

  公开号：JP2003261568A

  公开（公告）日：2003-09-19
• Synthesis of (NH)_<i>m</i>(NMe)_4−<i>m</i>-Bridged Calix[4]pyridines and the Effect of NH Bridge on Structure and Properties
  作者：En-Xuan Zhang、De-Xian Wang、Zhi-Tang Huang、Mei-Xiang Wang

  DOI：10.1021/jo901609u

  日期：2009.11.20

  The (NH)(m)(NMe)(4-m)-bridged calix[4]pyridines (m = 1-4) 19-23 were synthesized in excellent yields from deprotection of N-allyl groups of (NAllyl)(m)(NMe)(4-m)-bridged calix[4]pyridine derivatives 8 and 15-18, which were prepared in moderate yields by macrocyclic 2+2 and 1+3 coupling reactions between simple diamino- and dibromo-substituted fragments, In the solid state, (NH)(m)(NMe)(4-m)-bridged calix[4]pyridines adopted different 1,3-alternate conformations due to mainly the formation of varied conjugation systems of bridging NH units with their neighboring pyridines. In solution, all (NH)(m)(NMe)(4-m)-bridged calix[4]pyridines were very fluxional and the rates of interconversion of various conformational structures were very rapid relative to the NMR time scale, While (NH)(4)-bridged calix[4]pyridine 23 formed the strongest conjugation system, (NH)(2)(NMe)(2)-bridged calix[4]pyridine 21 acted as a selective fluorescence probe in the recognition of zinc(II) ion in solution with the dramatic enhancement of fluorescence intensity.