dimethyl 1-tert-butyloxycarbonyl-1,4-dihydro-4-phenylpyridine-3,5-dicarboxylate | 252669-41-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: dimethyl 1-tert-butyloxycarbonyl-1,4-dihydro-4-phenylpyridine-3,5-dicarboxylate
• 英文别名: 1-O-tert-butyl 3-O,5-O-dimethyl 4-phenyl-4H-pyridine-1,3,5-tricarboxylate
• CAS: 252669-41-3
• 化学式: C₂₀H₂₃NO₆
• 分子量: 373.406
• InChiKey: PAVJVXLOSFYILB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 1-tert-butyloxycarbonyl-1,4-dihydro-4-phenylpyridine-3,5-dicarboxylate 以 四氢呋喃 为溶剂， 反应 672.0h， 以70%的产率得到
  参考文献：
  名称：

  笼二聚体4-芳基-1,4-二氢吡啶类化合物作为开发新型HIV-1蛋白酶抑制剂的有前途的先导结构。

  摘要：

  DOI：

  10.1002/(sici)1521-4184(19991)332:1<3::aid-ardp3>3.0.co;2-1
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 dimethyl 4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以79%的产率得到dimethyl 1-tert-butyloxycarbonyl-1,4-dihydro-4-phenylpyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Rotameric Properties of Novel N-Acyl and N-Acyloxy Dimeric 4-Phenyl-1,4-dihydropyridines Derived from Developed Solid-State Synthesis

  摘要：

  Novel N-acyl and N-acyloxy dimeric 4-phenyl-1,4-dihydropyridines are given by solid-state photodimerization of their monomeric educts in excellent yields. The existence of rotamers was demonstrated by H-1 NMR spectroscopical measurement at certain temperatures and additionally supported by X-Ray crystal structure analysis of centrosymmetrical cage-dimeric N-acetyl-3,5-dimethoxycarbonyl-4-phenyl-1,4-dihydropyridine (3b). Topochemical investigations by X-Ray crystal structure analysis prove the formation of anti-dimeric N-Boc-3,5-dimethoxycarbonyl-4-phenyl-1,4-dihydropyridine (4e) to be controlled by the nearest distance of potentially reacting double bonds with 3.667(3) Angstrom.

  DOI：

  10.3987/com-99-8627

文献信息

• Cage DimericN-Acyl- andN-Acyloxy-4-aryl-1,4-dihydropyridines as First Representatives of a Novel Class of HIV-1 Protease Inhibitors
  作者：Andreas Hilgeroth、Andreas Billich

  DOI：10.1002/(sici)1521-4184(199911)332:11<380::aid-ardp380>3.0.co;2-t

  日期：1999.11

  The synthesis of a series of novel cage dimeric N-acyl and N-acyl-oxy-3-aryl-1,4-dihydropyridines starting either from solid-state synthetic ester dimers or hom monomeric 4-aryl-1,4-dihydropyridines is presented. Their biological evaluation as novel HIV-1 protease inhibitors showed the most active compounds to be 5c and 5i with inhibitory activities of 52% (50 mu M) and 49% (25 mu M), respectively. Within each series of N-acyl- and N-acyloxy derivatives NCOBz and NBoc groups were found to be the best substituents. Although they exhibiting only moderate activities these cage dimers hold promise as a class of novel non-peptidic HIV-1 protease inhibitors.
• Rotameric Properties of Novel N-Acyl and N-Acyloxy Dimeric 4-Phenyl-1,4-dihydropyridines Derived from Developed Solid-State Synthesis
  作者：Andreas Hilgeroth、Ute Baumeister、Frank Heinemann

  DOI：10.3987/com-99-8627

  日期：——

  Novel N-acyl and N-acyloxy dimeric 4-phenyl-1,4-dihydropyridines are given by solid-state photodimerization of their monomeric educts in excellent yields. The existence of rotamers was demonstrated by H-1 NMR spectroscopical measurement at certain temperatures and additionally supported by X-Ray crystal structure analysis of centrosymmetrical cage-dimeric N-acetyl-3,5-dimethoxycarbonyl-4-phenyl-1,4-dihydropyridine (3b). Topochemical investigations by X-Ray crystal structure analysis prove the formation of anti-dimeric N-Boc-3,5-dimethoxycarbonyl-4-phenyl-1,4-dihydropyridine (4e) to be controlled by the nearest distance of potentially reacting double bonds with 3.667(3) Angstrom.
• 10.1002/(sici)1521-4184(19991)332:1<3::aid-ardp3>3.0.co;2-1
  作者：Hilgeroth, Andreas、Billich, Andreas

  DOI：10.1002/(sici)1521-4184(19991)332:1<3::aid-ardp3>3.0.co;2-1

  日期：——