4-methoxy-1-methylpyridinium trifluoromethanesulfonate | 1542131-22-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 4-methoxy-1-methylpyridinium trifluoromethanesulfonate
• 英文别名: 4-Methoxy-1-methylpyridin-1-ium trifluoromethanesulfonate；4-methoxy-1-methylpyridin-1-ium;trifluoromethanesulfonate
• CAS: 1542131-22-5
• 化学式: CF₃O₃S*C₇H₁₀NO
• 分子量: 273.233
• InChiKey: FQMMOTWIPHDWNQ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.57
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  78.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-methoxy-1-methylpyridinium trifluoromethanesulfonate 在 盐酸 、 水 、 lithium tri-t-butoxyaluminum hydride 、 copper(I) bromide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 乙基苯 为溶剂， 反应 10.84h， 生成 2-(1H-benzo[d]imidazol-2-yl)-1-methylpiperidin-4-one
  参考文献：
  名称：

  Development of a Concise, Asymmetric Synthesis of a Smoothened Receptor (SMO) Inhibitor: Enzymatic Transamination of a 4-Piperidinone with Dynamic Kinetic Resolution

  摘要：

  A concise, asymmetric synthesis of a smoothened receptor inhibitor (1) is described. The synthesis features an enzymatic transamination with concurrent dynamic kinetic resolution (DKR) of a 4-piperidone (4). to establish the two stereogenic centers required in a single step. This efficient reaction affords the desired anti amine (3) in >10:1 dr and >99% ee. The title compound is prepared in only five steps with 40% overall yield.

  DOI：

  10.1021/ol403630g
• 作为产物：
  描述：

  4-甲氧基吡啶 、 三氟甲烷磺酸甲酯 以 二氯甲烷 为溶剂， 反应 1.0h， 以99%的产率得到4-methoxy-1-methylpyridinium trifluoromethanesulfonate
  参考文献：
  名称：

  Development of a Concise, Asymmetric Synthesis of a Smoothened Receptor (SMO) Inhibitor: Enzymatic Transamination of a 4-Piperidinone with Dynamic Kinetic Resolution

  摘要：

  A concise, asymmetric synthesis of a smoothened receptor inhibitor (1) is described. The synthesis features an enzymatic transamination with concurrent dynamic kinetic resolution (DKR) of a 4-piperidone (4). to establish the two stereogenic centers required in a single step. This efficient reaction affords the desired anti amine (3) in >10:1 dr and >99% ee. The title compound is prepared in only five steps with 40% overall yield.

  DOI：

  10.1021/ol403630g
• 作为试剂：
  描述：

  4-methoxy-1-methylpyridinium trifluoromethanesulfonate 、 1-对甲苯磺酰基苯并咪唑 在 4-methoxy-1-methylpyridinium trifluoromethanesulfonate 作用下， 以75的产率得到1-methyl-2-(1-tosyl-1H-benzo[d]imidazol-2-yl)-2,3-dihydropyridin-4(1H)-one
  参考文献：
  名称：

  Org. Lett. 2014, 16, 860-863

  摘要：

  DOI：

文献信息

• IR and NMR Reaction Monitoring Techniques for Nucleophilic Addition Reactions: In Situ Monitoring of the Addition of Benzimidazole to a Pyridinium Salt
  作者：Michele T. Drexler、David A. Foley、Howard W. Ward、Hugh J. Clarke

  DOI：10.1021/acs.oprd.5b00029

  日期：2015.9.18

  of in situ FTIR spectroscopy and online NMR to study the nucleophilic addition of benzimidazole analogues to an N-methylpyridinium salt. The reaction consists of two stages. First, the protected benzimidazole was lithiated with LDA to form the C-2 lithiated benzimidazole. The lithiated benzimidazole was then added to the pyridinium salt to generate the coupled product. The lithiated benzimidazole was

  这项研究集中于使用原位FTIR光谱和在线NMR研究苯并咪唑类似物向N的亲核加成-甲基吡啶鎓盐。该反应包括两个阶段。首先，将受保护的苯并咪唑用LDA锂化以形成C-2锂化的苯并咪唑。然后将锂化的苯并咪唑添加到吡啶鎓盐中以产生偶联产物。锂化的苯并咪唑不是热稳定的，因此离线采样具有挑战性。需要对锂化反应的完成有一个很好的了解，以便对过程有所了解，并为确定整个添加顺序中锂化苯并咪唑的去向提供基础。原位FTIR和在线NMR提供了在线方法来监测反应顺序和研究锂化苯并咪唑的温度依赖性稳定性。
• Development of a Concise, Asymmetric Synthesis of a Smoothened Receptor (SMO) Inhibitor: Enzymatic Transamination of a 4-Piperidinone with Dynamic Kinetic Resolution
  作者：Zhihui Peng、John W. Wong、Eric C. Hansen、Angela L. A. Puchlopek-Dermenci、Hugh J. Clarke

  DOI：10.1021/ol403630g

  日期：2014.2.7

  A concise, asymmetric synthesis of a smoothened receptor inhibitor (1) is described. The synthesis features an enzymatic transamination with concurrent dynamic kinetic resolution (DKR) of a 4-piperidone (4). to establish the two stereogenic centers required in a single step. This efficient reaction affords the desired anti amine (3) in >10:1 dr and >99% ee. The title compound is prepared in only five steps with 40% overall yield.
• Org. Lett. 2014, 16, 860-863
  作者：

  DOI：——

  日期：——