ethyl 4-phenyl-1-phenoxycarbonyl-1,4-dihydropyridine-3-carboxylate | 461679-43-6

• 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 4-phenyl-1-phenoxycarbonyl-1,4-dihydropyridine-3-carboxylate
• 英文别名: 3-O-ethyl 1-O-phenyl 4-phenyl-4H-pyridine-1,3-dicarboxylate
• CAS: 461679-43-6
• 化学式: C₂₁H₁₉NO₄
• 分子量: 349.386
• InChiKey: KFQCCIJQGJDPPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 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 4-phenyl-1-phenoxycarbonyl-1,4-dihydropyridine-3-carboxylate 以 四氢呋喃 为溶剂， 反应 672000.5h， 生成 diethyl 1,5-di-tert-butoxycarbonyl-1,5,8,8bα-tetrahydro-4,8-diphenylcyclobuta[1,2-b:3,4-b']dipyridine-4a,8aβ(4H,4bβH)-dicarboxylate
  参考文献：
  名称：

  Using Molecular Symmetry to Form New Drugs: Hydroxymethyl-Substituted 3,9-Diazatetraasteranes as the First Class of Symmetric MDR Modulators

  摘要：

  DOI：

  10.1002/1521-3773(20021004)41:19<3623::aid-anie3623>3.0.co;2-v
• 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 4-phenyl-1-phenoxycarbonyl-1,4-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  Using Molecular Symmetry to Form New Drugs: Hydroxymethyl-Substituted 3,9-Diazatetraasteranes as the First Class of Symmetric MDR Modulators

  摘要：

  DOI：

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

文献信息

• Observations on the DDQ Oxidation of 1-Acyldihydropyridines - A Synthetic Application
  作者：Debra J. Wallace、Andrew D. Gibb、Ian F. Cottrell、Derek J. Kennedy、Karel M. J. Brands、Ulf H. Dolling

  DOI：10.1055/s-2001-17509

  日期：——

  A synthetic application of the rate difference in oxidation of regioisomerically substituted N-acyldihydropyridines is reported. This has allowed for isolation of pure 4-substituted pyridine isomers without the need for chromatography. Diels-Alder adducts between a dihydropyridine and DDQ were isolated and formation of novel hydroquinone ethers was also observed during some reactions.

  报道了区域异构取代的N-酰基二氢吡啶氧化速率差异的综合应用。这一方法使得无需色谱分离即可获得纯的4-取代吡啶异构体。在某些反应中，二氢吡啶与DDQ的Diels-Alder加合物被分离出来，并且观察到了新型的氢醌醚的形成。
• First Rotameric Anti Dimers and 3,9-Diazatetraasteranes from Unsymmetrically Substituted N-Acyl and N-Acyloxy-4-aryl-1,4-dihydropyridines
  作者：Andreas Hilgeroth、Frank W. Heinemann、Ute Baumeister

  DOI：10.3987/com-01-9423

  日期：——

  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.