diethyl 1,4-dihydro-2-(2-hydroxy-2-methylpropyl)-6-methyl-4-<2-(trifluoromethyl)phenyl>-3,5-pyridinedicarboxylate | 126179-79-1

• 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: diethyl 1,4-dihydro-2-(2-hydroxy-2-methylpropyl)-6-methyl-4-<2-(trifluoromethyl)phenyl>-3,5-pyridinedicarboxylate
• 英文别名: diethyl 2-(2-hydroxy-2-methylpropyl)-6-methyl-4-[2-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 126179-79-1
• 化学式: C₂₃H₂₈F₃NO₅
• 分子量: 455.474
• InChiKey: AJZSFZWSFOWRJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.21
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  84.86
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  diethyl 1,4-dihydro-2-(2-hydroxy-2-methylpropyl)-6-methyl-4-<2-(trifluoromethyl)phenyl>-3,5-pyridinedicarboxylate 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 22.0h， 以50%的产率得到diethyl 1,4-dihydro-2-(2-methyl-1-propenyl)-6-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：

  SKF 24260 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 diethyl 1,4-dihydro-2-(2-hydroxy-2-methylpropyl)-6-methyl-4-<2-(trifluoromethyl)phenyl>-3,5-pyridinedicarboxylate
  参考文献：
  名称：

  Metalation of 1,4-dihydropyridine esters

  摘要：

  DOI：

  10.1016/s0040-4039(00)99253-0

文献信息

• POINDEXTER, GRAHAM S.;FOLEY, MICHAEL A.;LICAUSE, JOSEPH F., TETRAHEDRON LETT., 30,(1989) N6, C. 3393-3396
  作者：POINDEXTER, GRAHAM S.、FOLEY, MICHAEL A.、LICAUSE, JOSEPH F.

  DOI：——

  日期：——