1-(3-bromopropyl)-4-dimethylaminopyridinium bromide

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(3-bromopropyl)-4-dimethylaminopyridinium bromide
• 英文别名: 1-(3-bromopropyl)-N,N-dimethylpyridin-1-ium-4-amine;bromide
• 化学式: Br*C₁₀H₁₆BrN₂
• 分子量: 324.058
• InChiKey: JUSOMCUSEWZQKA-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.17
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  7.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3-bromopropyl)-4-dimethylaminopyridinium bromide 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺-d7 、 乙腈 为溶剂， 反应 75.0h， 生成 dimethyl-(1-methyl-5,6-dihydro-1H,4H-1,3a,6a-triaza-benzo[e]azulen-9-yl)amine
  参考文献：
  名称：

  混合超级电子供体 - 制备和反应性。

  摘要：

  报道了中性有机电子给体，其特征是亚吡啶基-咪唑基、亚吡啶基-苯并咪唑基和咪唑基-苯并咪唑基键。吡啶亚-苯并咪唑亚和咪唑亚-苯并咪唑亚杂化系统被设计为第一个在室温下将碘芳烃转化为芳基的超级电子给体，并且实际上两者都显示出在室温下显着芳基形成的证据。更强的亚吡啶亚-咪唑亚基供体在适当条件下（供体的 3 当量）有效地将碘芳烃转化为芳基阴离子。过量氢化钠碱的存在对其中一些电子转移反应具有非常重要和选择性的影响，并提出了其基本原理。

  DOI：

  10.3762/bjoc.8.112
• 作为产物：
  描述：

  4-二甲氨基吡啶 、 1,3-二溴丙烷 以 乙腈 为溶剂， 以88%的产率得到1-(3-bromopropyl)-4-dimethylaminopyridinium bromide
  参考文献：
  名称：

  Search for the Pharmacophore of Bispyridinium-Type Allosteric Modulators of Muscarinic Receptors

  摘要：

  The bis(dichlorobenzyl) ether of the bispyridinium oxime TMB 4 stabilizes antagonist binding to M(2)-cholinoceptors which is indicative of an allosteric action. More than 10 derivatives of the lead compound were synthesized to investigate structure-activity relationships. The allosteric potency of the compounds was indicated by the concentrations which retarded the rate of dissociation of [H-3]N-methylscopolamine from porcine cardiac cholinoceptors by a factor of 2 (EC(50)). Compared with TMB 4, the bis(dichlorobenzyl) derivative 4a displayed a more than 200-fold higher potency (EC(50) = 4.7 mu M). One of the dichlorobenzyl groups could be replaced by a methyl group without loss of activity (EC(50) = 4.5 mu M). Further shortening of this end of the molecule was accompanied by a moderate decline in potency to a minimum of EC(50) = 26 mu M. The second quaternary nitrogen was not a prerequisite for an allosteric activity. It is concluded that one half of the lead compound is pivotal for an interaction with the allosteric site of the M(2)-cholinoceptor, whereas the opposite end of the molecule modulates the allosteric activity.

  DOI：

  10.1021/jm00036a008

文献信息

• Hybrid super electron donors – preparation and reactivity
  作者：Jean Garnier、Douglas W Thomson、Shengze Zhou、Phillip I Jolly、Leonard E A Berlouis、John A Murphy

  DOI：10.3762/bjoc.8.112

  日期：——

  for significant aryl radical formation at room temperature. The stronger pyridinylidene-imidazolylidene donor converts iodoarenes to aryl anions efficiently under appropriate conditions (3 equiv of donor). The presence of excess sodium hydride base has a very important and selective effect on some of these electron-transfer reactions, and a rationale for this is proposed.

  报道了中性有机电子给体，其特征是亚吡啶基-咪唑基、亚吡啶基-苯并咪唑基和咪唑基-苯并咪唑基键。吡啶亚-苯并咪唑亚和咪唑亚-苯并咪唑亚杂化系统被设计为第一个在室温下将碘芳烃转化为芳基的超级电子给体，并且实际上两者都显示出在室温下显着芳基形成的证据。更强的亚吡啶亚-咪唑亚基供体在适当条件下（供体的 3 当量）有效地将碘芳烃转化为芳基阴离子。过量氢化钠碱的存在对其中一些电子转移反应具有非常重要和选择性的影响，并提出了其基本原理。
• Search for the Pharmacophore of Bispyridinium-Type Allosteric Modulators of Muscarinic Receptors
  作者：Mario H. Botero Cid、Ulrike Holzgrabe、Evi Kostenis、Klaus Mohr、Christian Traenkle

  DOI：10.1021/jm00036a008

  日期：1994.5

  The bis(dichlorobenzyl) ether of the bispyridinium oxime TMB 4 stabilizes antagonist binding to M(2)-cholinoceptors which is indicative of an allosteric action. More than 10 derivatives of the lead compound were synthesized to investigate structure-activity relationships. The allosteric potency of the compounds was indicated by the concentrations which retarded the rate of dissociation of [H-3]N-methylscopolamine from porcine cardiac cholinoceptors by a factor of 2 (EC(50)). Compared with TMB 4, the bis(dichlorobenzyl) derivative 4a displayed a more than 200-fold higher potency (EC(50) = 4.7 mu M). One of the dichlorobenzyl groups could be replaced by a methyl group without loss of activity (EC(50) = 4.5 mu M). Further shortening of this end of the molecule was accompanied by a moderate decline in potency to a minimum of EC(50) = 26 mu M. The second quaternary nitrogen was not a prerequisite for an allosteric activity. It is concluded that one half of the lead compound is pivotal for an interaction with the allosteric site of the M(2)-cholinoceptor, whereas the opposite end of the molecule modulates the allosteric activity.