dimethyl 1,4-dihydro-2-methyl-6-<(methylthio)methyl>-4-<2-(trifluoromethyl)phenyl>-3,5-pyridinedicarboxylate | 149143-25-9

• 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: dimethyl 1,4-dihydro-2-methyl-6-<(methylthio)methyl>-4-<2-(trifluoromethyl)phenyl>-3,5-pyridinedicarboxylate
• 英文别名: dimethyl 2-methyl-6-(methylsulfanylmethyl)-4-[2-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 149143-25-9
• 化学式: C₁₉H₂₀F₃NO₄S
• 分子量: 415.433
• InChiKey: SUPRTSSJGSUSMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  dimethyl 1,4-dihydro-2-methyl-6-<(methylthio)methyl>-4-<2-(trifluoromethyl)phenyl>-3,5-pyridinedicarboxylate 在 正丁基锂 、 氘代甲醇-d 作用下， 反应 2.5h， 生成 dimethyl 2-(monodeuteromethyl)-1,4-dihydro-6-bis<(methylthio)methyl>-4-<2-(trifluoromethyl)phenyl>-3,5-pyridinedicarboxylate
  参考文献：
  名称：

  Metalation of Hantzsch esters and mixed amide esters: a general route to C-2 functionalized 1,4-dihydropyridines

  摘要：

  1,4-Dihydropyridine (Hantzsch) diesters 3a-e readily undergo metalation at the C-2 methyl (vinylogous ester) position on treatment with alkyllithium bases. The resulting anion intermediates can be treated with electrophilic reagents to afford 1,4-dihydropyridine products that have been chemically elaborated at the C-2 methyl position. The methodology permits a variety of electrophilic functionalities to be regiospecifically introduced at the C-2 methyl position of 1,4-dihydropyridines. Deuterium distribution studies with mixed dihydropyridine amide esters 20a and 20b having nonequivalent C-2 and C-6 methyl groups indicate specific metalation occurs at the C-2 methyl (vinylogous ester) position. Tri- and tetraanion formation is also possible at both vinylogous methyl and NH positions when the metalation reactions are performed with excess equivalents of n-BuLi or 8-BuLi bases.

  DOI：

  10.1021/jo00067a012
• 作为产物：
  描述：

  二甲基二硫 、 1,4-二氢-2,6-二甲基-4-[O-(三氟甲基)苯基]-3,5-吡啶二甲酸二甲酯 在 正丁基锂 作用下， 生成 dimethyl 1,4-dihydro-2-methyl-6-<(methylthio)methyl>-4-<2-(trifluoromethyl)phenyl>-3,5-pyridinedicarboxylate 、 dimethyl 1,4-dihydro-2,6-bis<(methylthio)methyl>-4-<2-(trifluoromethyl)phenyl>-3,5-pyridinedicarboxylate
  参考文献：
  名称：

  Metalation of Hantzsch esters and mixed amide esters: a general route to C-2 functionalized 1,4-dihydropyridines

  摘要：

  1,4-Dihydropyridine (Hantzsch) diesters 3a-e readily undergo metalation at the C-2 methyl (vinylogous ester) position on treatment with alkyllithium bases. The resulting anion intermediates can be treated with electrophilic reagents to afford 1,4-dihydropyridine products that have been chemically elaborated at the C-2 methyl position. The methodology permits a variety of electrophilic functionalities to be regiospecifically introduced at the C-2 methyl position of 1,4-dihydropyridines. Deuterium distribution studies with mixed dihydropyridine amide esters 20a and 20b having nonequivalent C-2 and C-6 methyl groups indicate specific metalation occurs at the C-2 methyl (vinylogous ester) position. Tri- and tetraanion formation is also possible at both vinylogous methyl and NH positions when the metalation reactions are performed with excess equivalents of n-BuLi or 8-BuLi bases.

  DOI：

  10.1021/jo00067a012