methyl 1-benzyl-4-phenyl-1,4-dihydropyridine-3-carboxylate | 263747-27-9

• 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: methyl 1-benzyl-4-phenyl-1,4-dihydropyridine-3-carboxylate
• 英文别名: methyl 1-benzyl-4-phenyl-4H-pyridine-3-carboxylate
• CAS: 263747-27-9
• 化学式: C₂₀H₁₉NO₂
• 分子量: 305.376
• InChiKey: ZJWXAJHLHOWUID-UHFFFAOYSA-N

物化性质

• 熔点：
  80-82 °C
• 沸点：
  455.9±45.0 °C(Predicted)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 1-benzyl-4-phenyl-1,4-dihydropyridine-3-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1344000.0h， 生成 3,9-dibenzyl-1,7-dihydroxymethyl-6,12-diphenyl-3,9-diazahexacyclo[6.4.0.0^2.7.0^4.11.0^5.10]dodecane
  参考文献：
  名称：

  Biological Evaluation of Bishydroxymethyl-Substituted Cage Dimeric 1,4-Dihydropyridines as a Novel Class of P-Glycoprotein Modulating Agents in Cancer Cells

  摘要：

  A series of N-substituted cage dimeric 1,4-dihydropyridines 3a-e was evaluated as inhibitors of membrane efflux pump P-glycoprotein (P-gp) in multidrug resistant (mdr) cancer cells. Structure-activity relationships (SAR) and cytotoxic properties are discussed. Effective concentrations for overcoming mdr have been demonstrated in competition studies with the P-gp substrate epirubicin.

  DOI：

  10.1021/jm058046w
• 作为产物：
  描述：

  肉桂醛 、 (E/Z)-methyl 3-(benzylamino)acrylate 在 lanthanum(lll) triflate 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到methyl 1-benzyl-4-phenyl-1,4-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  杂化化合物4H-吡喃并[2,3-b]吡啶衍生物的有机催化合成及生物活性评价

  摘要：

  摘要 1,4-二氢吡啶和4H-吡喃衍生物是各种药物化合物中常见且重要的结构。二氢吡啶是化合物中众所周知的部分，具有镇痛、杀真菌和抗菌活性，4H-吡喃结构在具有抗菌和抗癌潜力的化合物中很常见；通过探索具有这两种杂环官能团组合的杂化化合物来利用 1,4-二氢吡啶和 4H-吡喃部分的生物活性是一个有趣的研究途径。在这项研究中，我们开发了在有机催化条件下产生的新型 1,4-二氢吡啶和 4H-吡喃杂化化合物，并评估了它们对 KB 和 HepG2 癌细胞系的细胞毒活性。图形概要

  DOI：

  10.1080/00397911.2020.1757717

文献信息

• Organocatalyzed regioselective and enantioselective synthesis of 1,4- and 1,2-dihydropyridines
  作者：Truong-Giang Le、Hoai-Thu Pham、James P. Martin、Isabelle Chataigner、Jean-Luc Renaud

  DOI：10.1080/00397911.2020.1778034

  日期：2020.9.1

  first examples of asymmetric organocatalyzed synthesis of 1,2-dihydropyridines, affording enantioselective access to and partially solving regioselectivity challenges in the synthesis of dihydropyridines. We demonstrate that through modification of organocatalysts both 1,2- and 1,4-dihydropyridines (1,2- and 1,4-DHPs) can be obtained with high regioselectivity (ratio of 1,2-DHP/1,4-DHP from 95/5 to 0/100)

  摘要在此，我们介绍了 1,2-二氢吡啶不对称有机催化合成的第一个例子，提供了对映选择性访问并部分解决了二氢吡啶合成中的区域选择性挑战。我们证明，通过有机催化剂的改性，可以以高区域选择性（1,2-DHP/1,4-DHP 的比率）获得 1,2- 和 1,4- 二氢吡啶（1,2- 和 1,4-DHP）从 95/5 到 0/100）和对映选择性（1,2-DHP 的 ee 为 33%，1,4-DHP 的 ee 高达 98%），产率高（高达 87%）。图形概要
• 10.3762/bjoc.20.126
  作者：Chen, Xiu-Yu、Han, Ying、Sun, Jing、Yan, Chao-Guo

  DOI：10.3762/bjoc.20.126

  日期：——

  polyfunctionalized tetrahydrocyclopenta[4,5]pyrrolo[2,3-b]pyridine-3,4b,5,6,7(1H)-pentacarboxylates was developed by a three-component reaction. In the absence of any catalyst, the three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates and 5,6-unsubstituted 1,4-dihydropyridines in refluxing acetonitrile afforded polyfunctionalized tetrahydrocyclopenta[4,5]pyrrolo[2,3-b]pyridine-3,4b,5,6,7(1H)-pentacarboxylates

   抽象的 通过三组分反应开发了一种有效合成多官能化四氢环戊[4,5]吡咯并[2,3- b ]吡啶-3,4b,5,6,7(1 H )-五甲酸酯的方案。在不存在任何催化剂的情况下，烷基异氰化物、二烷基丁-2-炔二酸酯和5,6-未取代的1,4-二氢吡啶在回流乙腈中发生三组分反应，得到多官能化四氢环戊[4,5]吡咯并[2,3- b ]吡啶-3,4b,5,6,7(1 H )-五甲酸酯，产率高，非对映选择性高。该反应通过将烷基异氰化物加成到两分子丁-2-炔二酸酯上原位生成活化的5-(烷基亚氨基)环戊-1,3-二烯，并与5,6进行连续的正式[3 + 2]环加成反应来完成-未取代的1,4-二氢吡啶。 Beilstein J. Org. Chem. 2024, 20, 1436–1443. doi:10.3762/bjoc.20.126
• Formation of Novel Photodimers from 4-Aryl-1,4-dihydropyridines
  作者：Andreas Hilgeroth、Ute Baumeister

  DOI：10.1002/1521-3765(20011105)7:21<4599::aid-chem4599>3.0.co;2-u

  日期：2001.11.5

  N-substituted 3-alkoxycarbonyl-4-aryl-1,4-dihydropyridines have been photochemically investigated for the first time. In contrast to reports of analogous 3,5-dialkoxycarbonyl derivatives, they are unreactive in the solid state with shortest distances of potentially reacting double bonds of 6.883(3) A for one derivative examined by x-ray crystal structure analysis. Solution irradiation with unfiltered light (lambda greater than or equal to 270 nm) led to novel diazatetrakis-homocubanes in 30-50% yields. Diazatetrakishomocubanes were also obtained by irradiation with filtered light (lambda > 313 nm) besides head-to-tail connected syn-dimers. The irradiation of the syn-dimers with unfiltered light led to centrosymmetric cage dimers accompanied by some dimer fragmentation. Formation of the homocubanes via intermediate biradicals is supported by the available data.
• The First Functionalized 6,12-Diazatetrakishomocubanes
  作者：Andreas Hilgeroth、Ute Baumeister

  DOI：10.1002/(sici)1521-3773(20000204)39:3<576::aid-anie576>3.0.co;2-g

  日期：2000.2.4

  The photodimerization of asymmetric 4-aryl-1,4-dihydropyridines results, totally unexpectedly, in the new 6,12-diazatetrakishomocubanes 1. This is in contrast to the previously observed [2+2] photocycloaddition reactions of symmetrical 4-aryl-1,4-dihydropyridines
• Organocatalyzed synthesis and biological activity evaluation of hybrid compounds 4<i>H</i>-pyrano[2,3-<i>b</i>]pyridine derivatives
  作者：Hoai-Thu Pham、James P. Martin、Truong-Giang Le

  DOI：10.1080/00397911.2020.1757717

  日期：2020.6.17

  pharmaceutical compounds. Dihydropyridines are well-known moieties in compounds that have analgesic, fungicidal, and antibacterial activities and 4H-pyran structures are populous in compounds with antibacterial and anti-cancer potential; exploiting the biological activities of both 1,4-dihydropyridines and 4H-pyran moieties through the exploration of hybrid compounds featuring combinations of these two

  摘要 1,4-二氢吡啶和4H-吡喃衍生物是各种药物化合物中常见且重要的结构。二氢吡啶是化合物中众所周知的部分，具有镇痛、杀真菌和抗菌活性，4H-吡喃结构在具有抗菌和抗癌潜力的化合物中很常见；通过探索具有这两种杂环官能团组合的杂化化合物来利用 1,4-二氢吡啶和 4H-吡喃部分的生物活性是一个有趣的研究途径。在这项研究中，我们开发了在有机催化条件下产生的新型 1,4-二氢吡啶和 4H-吡喃杂化化合物，并评估了它们对 KB 和 HepG2 癌细胞系的细胞毒活性。图形概要