6'-chloroanabaseine | 475589-04-9

• 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: 6'-chloroanabaseine
• 英文别名: 2-(6-chloro-pyridin-3-yl)-3,4,5,6-tetrahydropyridine；2-Chloro-5-(2,3,4,5-tetrahydropyridin-6-yl)pyridine
• CAS: 475589-04-9
• 化学式: C₁₀H₁₁ClN₂
• 分子量: 194.664
• InChiKey: JCXKHMWMMJYXRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4-二甲氧基苯甲醛 、 6'-chloroanabaseine 在 sodium acetate 、 溶剂黄146 作用下， 以35%的产率得到6'-chloro-3-(2,4-dimethoxybenzylidene)anabaseine
  参考文献：
  名称：

  Structure–activity relationships of benzylidene anabaseines in nicotinic acetylcholine receptors of cockroach nerve cords

  摘要：

  Ten analogues of 6'-chloro-3-benzylideneanabaseine (CBA) bearing substituents Lit the ortho- and the para-positions of the phenyl group were synthesized, together with two related compounds, The affinity of the synthesized compounds for nicotinic acetylcholine receptors (nAChRs) in the nerve cord of the American cockroach (Periplancta americana L.) was examined by the radioligand binding assay using [H-3]epibatidine (EPI), a nAChR agonist. All 12 tested compounds inhibited [3H]EPI binding, showing K-i values ranging from 14.6 to 6830 nM. The potency variation of para-substituted CBA analogues was explained by the steric (DeltaB(1)) and electronic (sigma(p)) parameters of the para-substituents, or by the steric parameter and the charge of the NI nitrogen atom (qN(1)). Among the CBA analogues. only two compounds containing a dimethylamino group and a methoxy group at the paraposition showed high insecticidal activity against the German cockroach (Blattella germanica) when injected after pretreatment with metabolic inhibitors. High-affinity analogues of CBA might be suitable probes for use in classifying and characterizing insect nAChR subtypes. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00139-6
• 作为产物：
  描述：

  3,4,5,6-Tetrahydro-[2,3']bipyridinyl-6'-ol; compound with GENERIC INORGANIC NEUTRAL COMPONENT 在 三氯氧磷 作用下， 生成 6'-chloroanabaseine
  参考文献：
  名称：

  Structure–activity relationships of benzylidene anabaseines in nicotinic acetylcholine receptors of cockroach nerve cords

  摘要：

  Ten analogues of 6'-chloro-3-benzylideneanabaseine (CBA) bearing substituents Lit the ortho- and the para-positions of the phenyl group were synthesized, together with two related compounds, The affinity of the synthesized compounds for nicotinic acetylcholine receptors (nAChRs) in the nerve cord of the American cockroach (Periplancta americana L.) was examined by the radioligand binding assay using [H-3]epibatidine (EPI), a nAChR agonist. All 12 tested compounds inhibited [3H]EPI binding, showing K-i values ranging from 14.6 to 6830 nM. The potency variation of para-substituted CBA analogues was explained by the steric (DeltaB(1)) and electronic (sigma(p)) parameters of the para-substituents, or by the steric parameter and the charge of the NI nitrogen atom (qN(1)). Among the CBA analogues. only two compounds containing a dimethylamino group and a methoxy group at the paraposition showed high insecticidal activity against the German cockroach (Blattella germanica) when injected after pretreatment with metabolic inhibitors. High-affinity analogues of CBA might be suitable probes for use in classifying and characterizing insect nAChR subtypes. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00139-6

文献信息

• Iridium-Catalyzed Asymmetric Hydrogenation of 2-Pyridyl Cyclic Imines: A Highly Enantioselective Approach to Nicotine Derivatives
  作者：Cui Guo、Dong-Wei Sun、Shuang Yang、Shen-Jie Mao、Xiao-Hua Xu、Shou-Fei Zhu、Qi-Lin Zhou

  DOI：10.1021/ja511422q

  日期：2015.1.14

  A highly efficient asymmetric hydrogenation of cyclic imines containing a pyridyl moiety was established by using iridium catalysts with chiral spiro phosphine-oxazoline ligands. This process will facilitate the development of new nicotine-related pharmaceuticals. The introduction of a substituent at the ortho position of the pyridyl ring to reduce its coordinating ability ensures the success of the

  通过使用具有手性螺环膦-恶唑啉配体的铱催化剂，建立了含有吡啶基部分的环状亚胺的高效不对称氢化。这一过程将促进新的尼古丁相关药物的开发。在吡啶环的邻位引入取代基以降低其配位能力确保了氢化的成功和优异的对映选择性。