dimethyl 4-(4-formylphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate | 121497-14-1

• 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 4-(4-formylphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 121497-14-1
• 化学式: C₁₈H₁₉NO₅
• 分子量: 329.353
• InChiKey: UXEINALMTKRBNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 4-(4-formylphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate 在 三氟化硼乙醚 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 tetramethyl 4,4'-(10,20-diphenylporphyrin-5,15-diyldibenzene-4,1-diyl)bis(2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate)
  参考文献：
  名称：

  Synthesis and photophysical evaluation of meso-phenyl-1,4-dihydropyridineand pyridine-porphyrin hybrids

  摘要：

  在本研究中，我们合成了一种新的分子杂化物，它由卟啉环系统组成，在中间位置与苯基连接，并通过对苯基连接子与1,4-二氢吡啶或吡啶部分连接。通常，在时间修正的Adler-Longo程序下，定向使用二氢吡啶醛可获得最佳的总产量，得到以下一般式为A1B3、A2B2或A4的中间取代二氢吡啶-卟啉，其中A代表苯基-二氢吡啶，B代表苯基取代基。相应的中间取代吡啶-卟啉杂化物是通过用2,3-二氯-5,6-二氰基-1,4-苯醌氧化二氢吡啶-卟啉得到的。A4二氢吡啶-卟啉的紫外-可见光谱带出乎意料地发生了红移，具有罗多卟啉Q带谱。还发现，1O2的产生增加与杂化分子中二氢吡啶或吡啶部分的数量增加有关。所有卟啉杂化物

  DOI：

  10.1007/s10593-021-03043-w
• 作为产物：
  描述：

  3-氨基巴豆酸甲酯 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 25.0h， 生成 dimethyl 4-(4-formylphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Syntheses and bioevaluation of substituted dihydropyridines for pregnancy-interceptive activity in hamsters

  摘要：

  A number of 2,6-dimethyl-3,5-bis(methoxycarbonyl)-4-substituted-1,4- dihydropyridines were synthesized and evaluated for pregnancy-interceptive activity in mated hamsters. Out of 24 compounds, 12, 15, 21, 22, 28, and 34 caused a marked reduction in the number of implantations when administered on days 3-8 postcoitum. In an in vitro competition assay, none of the compounds exhibited noticeable binding affinity for uterine progesterone receptors. The results reported here have helped to identify new leads for developing pregnancy-interceptive agents and the active compounds do not seem to elicit their interceptive effect through receptor-mediated inhibition of progesterone action in hamster uterus.

  DOI：

  10.1021/jm00130a012

文献信息

• <scp>l</scp>-Tyrosine loaded nanoparticles: an efficient catalyst for the synthesis of dicoumarols and Hantzsch 1,4-dihydropyridines
  作者：Anamika Khaskel、Pranjit Barman、Utpal Jana

  DOI：10.1039/c4ra16627b

  日期：——

  l-Tyrosine loaded nanoparticles catalyzed organic reactions.

  -酪氨酸载荷的纳米颗粒催化有机反应。
• MUKHERJEE, ANITA;AKHTAR, MOHAMMAD S.;SHARMA, VISHNU L.;SETH, MANJU;BHADUR+, J. MED. CHEM., 32,(1989) N0, C. 2297-2300
  作者：MUKHERJEE, ANITA、AKHTAR, MOHAMMAD S.、SHARMA, VISHNU L.、SETH, MANJU、BHADUR+

  DOI：——

  日期：——
• Syntheses and bioevaluation of substituted dihydropyridines for pregnancy-interceptive activity in hamsters
  作者：Anita Mukherjee、Mohammad S. Akhtar、Vishnu L. Sharma、Manju Seth、Amiya P. Bhaduri、Anila Agnihotri、Purshottam K. Mehrotra、Ved Prakash Kamboj

  DOI：10.1021/jm00130a012

  日期：1989.10

  A number of 2,6-dimethyl-3,5-bis(methoxycarbonyl)-4-substituted-1,4- dihydropyridines were synthesized and evaluated for pregnancy-interceptive activity in mated hamsters. Out of 24 compounds, 12, 15, 21, 22, 28, and 34 caused a marked reduction in the number of implantations when administered on days 3-8 postcoitum. In an in vitro competition assay, none of the compounds exhibited noticeable binding affinity for uterine progesterone receptors. The results reported here have helped to identify new leads for developing pregnancy-interceptive agents and the active compounds do not seem to elicit their interceptive effect through receptor-mediated inhibition of progesterone action in hamster uterus.
• Synthesis and photophysical evaluation of meso-phenyl-1,4-dihydropyridineand pyridine-porphyrin hybrids
  作者：Lais Danciguer Guanaes、Matheus Murmel Guimarães、Diogo R. B. Ducatti、Maria Eugênia R. Duarte、Sandra M. W. Barreira、Miguel D. Noseda、Alan Guilherme Gonçalves

  DOI：10.1007/s10593-021-03043-w

  日期：2021.12

  In the present work, we have synthesized new molecular hybrids consisting of porphyrin ring system connected at the meso positions with phenyl groups and/or, through p-phenylene linkers, with 1,4-dihydropyridine or pyridine moieties. In general, the directed use of dihydropyridine aldehyde, under time-modified Adler–Longo procedures, gave the best overall yields of the following meso-substituted dihydropyridine-porphyrins of general formula A1B3, A2B2, or A4, where A stands for phenyl-dihydropyridine and B for phenyl substituents. The corresponding meso-substituted pyridine-porphyrin hybrids were obtained from oxidation of the dihydropyridineporphyrins with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. The UV-vis spectra bands of the A4 dihydropyridine-porphyrin were unexpectedly red-shifted, having a rhodoporphyrin Q-bands profile. It was also found that an increased production of 1O2 correlates with a higher number of dihydropyridine or pyridine moieties in the hybrid molecule. All porphyrin hybrids were considered adequate candidates to be employed in photodynamic therapy.

  在本研究中，我们合成了一种新的分子杂化物，它由卟啉环系统组成，在中间位置与苯基连接，并通过对苯基连接子与1,4-二氢吡啶或吡啶部分连接。通常，在时间修正的Adler-Longo程序下，定向使用二氢吡啶醛可获得最佳的总产量，得到以下一般式为A1B3、A2B2或A4的中间取代二氢吡啶-卟啉，其中A代表苯基-二氢吡啶，B代表苯基取代基。相应的中间取代吡啶-卟啉杂化物是通过用2,3-二氯-5,6-二氰基-1,4-苯醌氧化二氢吡啶-卟啉得到的。A4二氢吡啶-卟啉的紫外-可见光谱带出乎意料地发生了红移，具有罗多卟啉Q带谱。还发现，1O2的产生增加与杂化分子中二氢吡啶或吡啶部分的数量增加有关。所有卟啉杂化物