ethyl 1-methoxycarbonyl-4-phenyl-1,4-dihydropyridine-3-carboxylate | 461679-42-5

• 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: ethyl 1-methoxycarbonyl-4-phenyl-1,4-dihydropyridine-3-carboxylate
• 英文别名: 3-O-ethyl 1-O-methyl 4-phenyl-4H-pyridine-1,3-dicarboxylate
• CAS: 461679-42-5
• 化学式: C₁₆H₁₇NO₄
• 分子量: 287.315
• InChiKey: IPZOCKMNFSPPOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 1-methoxycarbonyl-4-phenyl-1,4-dihydropyridine-3-carboxylate 反应 672000.0h， 以70%的产率得到Ethyl 4-phenylpyridine-3-carboxylate
  参考文献：
  名称：

  First Rotameric Anti Dimers and 3,9-Diazatetraasteranes from Unsymmetrically Substituted N-Acyl and N-Acyloxy-4-aryl-1,4-dihydropyridines

  摘要：

  A series of unsymmetrically substituted N-acyl- and N-acyloxy-1,4-dihydropyridines (1) have been photochemically investigated. On irradiating the crystals of one derivative (la) containing centrosymmetrical pairs of molecules with a distance of 3.894(3) Angstrom between the potentially reacting double bonds favorable for a photodimerisation reaction, the formation of an anti-dimer (2a) was observed. Two other solid derivatives (1b, c) merely decomposed on irradiation to give substituted pyridine compound (3). Solution irradiation of 1,4-dihydropyridines (1) led to the centrosymmetric cage compounds 3,9-diazatetraasteranes (4) and to anti dimers (2) as main products, both existing as rotamers. Symmetric as well as rotameric properties of selected compounds (4) have been demonstrated by X-Ray crystal structure analysis and H-1 NMR spectroscopy.

  DOI：

  10.3987/com-01-9423
• 作为产物：
  描述：

  烟酸乙酯 在 copper(l) iodide 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 生成 ethyl 1-methoxycarbonyl-4-phenyl-1,4-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  First Rotameric Anti Dimers and 3,9-Diazatetraasteranes from Unsymmetrically Substituted N-Acyl and N-Acyloxy-4-aryl-1,4-dihydropyridines

  摘要：

  A series of unsymmetrically substituted N-acyl- and N-acyloxy-1,4-dihydropyridines (1) have been photochemically investigated. On irradiating the crystals of one derivative (la) containing centrosymmetrical pairs of molecules with a distance of 3.894(3) Angstrom between the potentially reacting double bonds favorable for a photodimerisation reaction, the formation of an anti-dimer (2a) was observed. Two other solid derivatives (1b, c) merely decomposed on irradiation to give substituted pyridine compound (3). Solution irradiation of 1,4-dihydropyridines (1) led to the centrosymmetric cage compounds 3,9-diazatetraasteranes (4) and to anti dimers (2) as main products, both existing as rotamers. Symmetric as well as rotameric properties of selected compounds (4) have been demonstrated by X-Ray crystal structure analysis and H-1 NMR spectroscopy.

  DOI：

  10.3987/com-01-9423

文献信息

• Using Molecular Symmetry to Form New Drugs: Hydroxymethyl-Substituted 3,9-Diazatetraasteranes as the First Class of Symmetric MDR Modulators
  作者：Andreas Hilgeroth、Jósef Molnár、Eric De Clercq

  DOI：10.1002/1521-3773(20021004)41:19<3623::aid-anie3623>3.0.co;2-v

  日期：2002.10.4