Methyl 2-(pyridin-4-ylthio)acetate | 78526-48-4

• 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-(pyridin-4-ylthio)acetate
• 英文别名: methyl 2-pyridin-4-ylsulfanylacetate
• CAS: 78526-48-4
• 化学式: C₈H₉NO₂S
• 分子量: 183.231
• InChiKey: KAEKXTVKSXUPON-UHFFFAOYSA-N

物化性质

• 沸点：
  283.7±20.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

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：

  Methyl 2-(pyridin-4-ylthio)acetate 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 2-(pyridin-4-ylthio)acetohydrazide
  参考文献：
  名称：

  N-Acylhydrazones as inhibitors of PDE10A

  摘要：

  Cyclic nucleotide phosphodiesterases (PDEs) are represented by a large superfamily of enzymes. A series of hydrazone-based inhibitors was synthesized and shown to be novel, potent, and selective against PDE10A. Optimized compounds of this class were efficacious in animal models of schizophrenia and may be useful for the treatment of this disease. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.100
• 作为产物：
  描述：

  4-羟基吡啶 在 劳森试剂 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 Methyl 2-(pyridin-4-ylthio)acetate
  参考文献：
  名称：

  N-Acylhydrazones as inhibitors of PDE10A

  摘要：

  Cyclic nucleotide phosphodiesterases (PDEs) are represented by a large superfamily of enzymes. A series of hydrazone-based inhibitors was synthesized and shown to be novel, potent, and selective against PDE10A. Optimized compounds of this class were efficacious in animal models of schizophrenia and may be useful for the treatment of this disease. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.100

文献信息

• Synthetic applications of N–N linked heterocycles. Part 12. The preparation of 4-alkylthio- and 4-arylthio-pyridines by regiospecific attack of thioalkoxide lons on N-(4-oxopyridin-1-yl)pyridinium salts
  作者：Michael P. Sammes、Christopher W. F. Leung、Chi Keung Mak、Alan R. Katritzky

  DOI：10.1039/p19810001585

  日期：——

  Thiolate ions add regiospecifically to N-(4-oxopyridin-1-yl)pyridinium salts (2)–(7) to give in good to excellent yields only the 1,4-dihydropyridine adducts (8)–(13), regardless of whether or not the pyridone moiety carries substituents for sterically shielding the 2- and 6-positions of the pyridinium ring. The addition is believed to be thermodynamically controlled. Decomposition of the dihydro-adducts

  硫醇离子对N-（4-氧代吡啶-1-基）吡啶鎓盐（2）-（7）呈区域特异性添加，仅产生1,4-二氢吡啶加合物（8）-（13）即可获得优异的优良收率吡啶酮部分是否带有取代基以立体屏蔽吡啶鎓环的2位和6位。据信该添加是热力学控制的。在自由基条件下或通过热解分解二氢加合物，尽管2-甲基加合物（9）反应失败，但吡啶4-基硫醚（14）和（16）的收率很高。还描述了6-甲基-4-氧杂吡喃-2-羧酸的改进的合成。
• 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。
• Ceric(IV) ammonium nitrate in the selective conversion of hydrazides to esters
  作者：Bogdan Štefane、Marijan Kočevar、Slovenko Polanc

  DOI：10.1016/s0040-4039(99)00764-9

  日期：1999.6

  Hydrazides were treated with ceric(IV) ammonium nitrate (CAN) in the presence of the appropriate alcohol as a nucleophile to afford esters in good yields. Reactions took place exclusively at the hydrazino moiety even when other sensitive groups were present in either of the partners. (C) 1999 Elsevier Science Ltd, All rights reserved.
• SAMMES M. P.; LEUNG C. W. F.; MAK C. K.; KATRITZKY A. R., J. CHEM. SOC. PERKIN TRANS., 1981, PART 1, NO 5, 1589-1590
  作者：SAMMES M. P.、 LEUNG C. W. F.、 MAK C. K.、 KATRITZKY A. R.

  DOI：——

  日期：——
• N-Acylhydrazones as inhibitors of PDE10A
  作者：Jennifer L. Gage、Rene Onrust、Derek Johnston、Andrew Osnowski、Wendy MacDonald、Lee Mitchell、László Ürögdi、Alex Rohde、Kevin Harbol、Sasha Gragerov、György Dormán、Tom Wheeler、Vince Florio、Neil S. Cutshall

  DOI：10.1016/j.bmcl.2011.05.100

  日期：2011.7

  Cyclic nucleotide phosphodiesterases (PDEs) are represented by a large superfamily of enzymes. A series of hydrazone-based inhibitors was synthesized and shown to be novel, potent, and selective against PDE10A. Optimized compounds of this class were efficacious in animal models of schizophrenia and may be useful for the treatment of this disease. (C) 2011 Elsevier Ltd. All rights reserved.