methyl 2-(3-pyridyl)mercaptoacetate

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: methyl 2-(3-pyridyl)mercaptoacetate
• 英文别名: Methyl 2-pyridin-3-ylsulfanylacetate；methyl 2-pyridin-3-ylsulfanylacetate
• 化学式: C₈H₉NO₂S
• 分子量: 183.231
• InChiKey: VNJGTRCCFYVKKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  64.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-甲基乙二胺 、 methyl 2-(3-pyridyl)mercaptoacetate 在 三甲基铝 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 3-(1-Methyl-4,5-dihydro-1H-imidazol-2-ylmethylsulfanyl)-pyridine
  参考文献：
  名称：

  Homoazanicotine:  A Structure-Affinity Study for Nicotinic Acetylcholine (nACh) Receptor Binding

  摘要：

  We have recently identified 3-[(1-methyl)-4,5-dihydro-1H-imidazol-2-yl)methyl]pyridine (homo-azanicotine, 8) as a novel nicotinic acetylcholinergic (nACh) receptor ligand. In the present investigation, after we determined that 8 binds selectively at nicotinic (K-i = 7.8 nM) vs muscarinic (K-i > 10 000 nM) acetylcholinergic receptors, we examined its structure-affinity relationships for nACh receptor binding. The features investigated included the influence of (i) the composition of connector that separates the two rings, (ii) the N-methyl group, (iii) the ring opening of the imidazoline ring, (iv) the pyridine nitrogen atom, and (v) the aromatization of the imidazoline ring on nACh receptor affinity. As with nicotine, the parent structure seems optimal and most structural changes reduce nACh receptor affinity. Also, as with nicotine analogues, alteration of the spacer group influences affinity in a manner that is somewhat different than that seen with the parent structure.

  DOI：

  10.1021/jm020188s
• 作为产物：
  描述：

  氯乙酸甲酯 、 sodium 3-mercaptopyridine 以 乙二醇二甲醚 为溶剂， 反应 12.0h， 以68%的产率得到methyl 2-(3-pyridyl)mercaptoacetate
  参考文献：
  名称：

  Homoazanicotine:  A Structure-Affinity Study for Nicotinic Acetylcholine (nACh) Receptor Binding

  摘要：

  We have recently identified 3-[(1-methyl)-4,5-dihydro-1H-imidazol-2-yl)methyl]pyridine (homo-azanicotine, 8) as a novel nicotinic acetylcholinergic (nACh) receptor ligand. In the present investigation, after we determined that 8 binds selectively at nicotinic (K-i = 7.8 nM) vs muscarinic (K-i > 10 000 nM) acetylcholinergic receptors, we examined its structure-affinity relationships for nACh receptor binding. The features investigated included the influence of (i) the composition of connector that separates the two rings, (ii) the N-methyl group, (iii) the ring opening of the imidazoline ring, (iv) the pyridine nitrogen atom, and (v) the aromatization of the imidazoline ring on nACh receptor affinity. As with nicotine, the parent structure seems optimal and most structural changes reduce nACh receptor affinity. Also, as with nicotine analogues, alteration of the spacer group influences affinity in a manner that is somewhat different than that seen with the parent structure.

  DOI：

  10.1021/jm020188s

文献信息

• General cross-coupling reactions with adaptive dynamic homogeneous catalysis
  作者：Indrajit Ghosh、Nikita Shlapakov、Tobias A. Karl、Jonas Düker、Maksim Nikitin、Julia V. Burykina、Valentine P. Ananikov、Burkhard König

  DOI：10.1038/s41586-023-06087-4

  日期：——

  (AD-HoC) with nickel under visible-light-driven redox reaction conditions for general C(sp2)–(hetero)atom coupling reactions. The self-adjustive nature of the catalytic system allowed the simple classification of dozens of various classes of nucleophiles in cross-coupling reactions. This is synthetically demonstrated in nine different bond-forming reactions (in this case, C(sp2)–S, Se, N, P, B, O, C(sp3, sp2

  交叉偶联反应是现代有机合成中最重要的转化之一1,2,3。尽管考虑到各种方案，报道的（杂）芳基卤化物和亲核试剂偶联配偶体的范围非常大，但化合物类别之间的反应条件差异很大，因此需要根据具体情况重新优化反应条件4。在这里，我们介绍了在可见光驱动的氧化还原反应条件下镍的自适应动态均相催化（AD-HoC），用于一般的 C( sp 2 )–(杂)原子偶联反应。催化系统的自我调节性质允许在交叉偶联反应中对数十种不同类别的亲核试剂进行简单分类。这在九种不同的成键反应（在本例中为 C( sp 2 )–S、Se、N、P、B、O、C( sp 3、  sp 2、  sp )、Si、Cl）中得到了综合证明在可预测的反应条件下进行数百个合成实例。催化反应中心和条件因添加的亲核试剂或如果需要而添加市售的廉价胺碱而彼此不同。
• Homoazanicotine:  A Structure-Affinity Study for Nicotinic Acetylcholine (nACh) Receptor Binding
  作者：G. Ferretti、M. Dukat、M. Giannella、A. Piergentili、M. Pigini、W. Quaglia、M. I. Damaj、B. R. Martin、R. A. Glennon

  DOI：10.1021/jm020188s

  日期：2002.10.1

  We have recently identified 3-[(1-methyl)-4,5-dihydro-1H-imidazol-2-yl)methyl]pyridine (homo-azanicotine, 8) as a novel nicotinic acetylcholinergic (nACh) receptor ligand. In the present investigation, after we determined that 8 binds selectively at nicotinic (K-i = 7.8 nM) vs muscarinic (K-i > 10 000 nM) acetylcholinergic receptors, we examined its structure-affinity relationships for nACh receptor binding. The features investigated included the influence of (i) the composition of connector that separates the two rings, (ii) the N-methyl group, (iii) the ring opening of the imidazoline ring, (iv) the pyridine nitrogen atom, and (v) the aromatization of the imidazoline ring on nACh receptor affinity. As with nicotine, the parent structure seems optimal and most structural changes reduce nACh receptor affinity. Also, as with nicotine analogues, alteration of the spacer group influences affinity in a manner that is somewhat different than that seen with the parent structure.