Phenylmethyl 3,6-dihydro-2-propyl-4-[[(trifluoromethyl)sulfonyl]oxy]-1(2H)-pyridinecarboxylate | 145100-59-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Phenylmethyl 3,6-dihydro-2-propyl-4-[[(trifluoromethyl)sulfonyl]oxy]-1(2H)-pyridinecarboxylate
• 英文别名: benzyl 2-propyl-4-(trifluoromethylsulfonyloxy)-3,6-dihydro-2H-pyridine-1-carboxylate
• CAS: 145100-59-0
• 化学式: C₁₇H₂₀F₃NO₅S
• 分子量: 407.411
• InChiKey: IRHOWPRVXUMLEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-[N,正双(三氟甲烷烷磺酰)氨基]-5-氯吡啶 、 4-氧代-2-丙基-3,4-二氢吡啶-1(2H)-羧酸苄酯 在 L-Selectride 作用下， 生成 Phenylmethyl 3,6-dihydro-2-propyl-4-[[(trifluoromethyl)sulfonyl]oxy]-1(2H)-pyridinecarboxylate
  参考文献：
  名称：

  Pyridine-derived triflating reagents: An improved preparation of vinyl triflates from metallo enolates.

  摘要：

  Metallo enolates of ketones are trapped with an N-(2-pyridyl)triflimide at low temperatures to give vinyl triflates.

  DOI：

  10.1016/s0040-4039(00)60957-7

文献信息

• Thermodynamic equilibration of dihydropyridone enolates: application to the total synthesis of (+/−)-epiuleine
  作者：Edward S. Tasber、Robert M. Garbaccio

  DOI：10.1016/j.tetlet.2003.10.030

  日期：2003.12

  as its vinyl triflate (3). This enolate interconversion is dependent on the dihydropyridone C-2 substituent and can be interpreted in terms of conformational analysis. This novel scaffold (3) opens another avenue for the strategic deployment of dihydropyridones into both natural product synthesis and drug discovery. To this end, this method is highlighted by its use as a key step in a total synthesis

  在将2-取代的二氢吡啶酮（1）还原成1,4-之后，可以将所需的“动力学”烯醇酸酯在加热后进行异构化，以分离出热力学烯醇酸酯作为其三氟甲磺酸乙烯酯（3）。该烯醇化物相互转化取决于二氢吡啶酮C-2取代基，并且可以根据构象分析来解释。这种新颖的支架（3）为将二氢吡啶酮类策略性部署到天然产物合成和药物发现中开辟了另一条途径。为此，该方法通过将其用作（+/-）Epiuleine（14）的全合成中的关键步骤而得到强调。
• Pyridine-derived triflating reagents: An improved preparation of vinyl triflates from metallo enolates.
  作者：Daniel L. Comins、Ali Dehghani

  DOI：10.1016/s0040-4039(00)60957-7

  日期：1992.10

  Metallo enolates of ketones are trapped with an N-(2-pyridyl)triflimide at low temperatures to give vinyl triflates.