2,6-dimethyl-4-(3-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester | 23118-50-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,6-dimethyl-4-(3-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester
• 英文别名: 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(alpha,alpha,alpha-trifluoro-m-tolyl)-, diethyl ester；diethyl 2,6-dimethyl-4-[3-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 23118-50-5
• 化学式: C₂₀H₂₂F₃NO₄
• 分子量: 397.394
• InChiKey: VWCSDMYARWZKBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,6-dimethyl-4-(3-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester 在 air 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Hantzsch 1,4-二氢吡啶的高非对映选择性光重排合成2,3-二氢吡咯

  摘要：

  发现Hantzsch 1,4-二氢吡啶在高非对映选择性（dr> 20：1）的LED光（410 nm）照射下通过空气进行光重排而转变为2,3-二氢吡咯。该反应包括串联光氧化/重排。从醛，乙酸铵和乙酰乙酸乙酯开始，通过一锅法成功地以中等收率获得了2,3-二氢吡咯。

  DOI：

  10.1016/j.tetlet.2017.02.041
• 作为产物：
  描述：

  diethyl (1R,9R,13R)-9,11-dimethyl-4-(trifluoromethyl)-8-thia-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5,11-tetraene-12,13-dicarboxylate 生成 2,6-dimethyl-4-(3-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  CLAREMON, D. A.;YOUNG, S. D., TETRAHEDRON LETT., 1985, 26, N 44, 5417-5420

  摘要：

  DOI：

文献信息

• 1,3,5-Tricarbo-1,4-dihydropyridines
  申请人：SmithKline Corporation

  公开号：US03956341A1

  公开（公告）日：1976-05-11

  N-Substituted 1,4-dihydropyridines are prepared by reaction of the corresponding N-unsubstituted 1,4-dihydropyridines with an alkyl haloformate, an acid halide or a carbamyl halide in the presence of base. These compounds have hypotensive activity.

  N-取代的1,4-二氢吡啶是通过在碱的存在下，将相应的N-未取代的1,4-二氢吡啶与烷基卤酸酯、酸卤或者氨基甲酸酯反应制备而成。这些化合物具有降压活性。
• Dihydropyridines as inhibitors of capacitative calcium entry in leukemic HL-60 cells
  作者：Jacquie L Harper、Carol S Camerini-Otero、An-Hu Li、Soon-Ai Kim、Kenneth A Jacobson、John W Daly

  DOI：10.1016/s0006-2952(02)01488-0

  日期：2003.2

  A series of 1,4-dihydropyridines (DHPs) were investigated as inhibitors of capacitative calcium influx through store-operated calcium (SOC) channels. Such channels activate after ATP-elicited release of inositol trisphosphate (IP3)-sensitive calcium stores in leukemia HL-60 cells. The most potent DHPs were those containing a 4-phenyl group with an electron-withdrawing substituent, such as m- or p-nitro- or in-trifluoromethyl (IC50 values: 3-6 muM). Benzyl esters, corresponding to the usual ethyl/methyl esters of the DHPs developed as L-type calcium channel blockers, retained potency at SOC channels, as did N-substituted DHPs. N-Methylation reduced by orders of magnitude the potency at L-type channels resulting in DHPs nearly equipotent at SOC and L-type channels. DHPs with N-ethyl, N-allyl, and N-propargyl groups also had similar potencies at SOC and L-type channels. Replacement of the usual 6-methyl group of DHPs with larger groups, such as cyclobutyl or phenyl, eliminated activity at the SOC channels; such DHPs instead elicited formation of inositol phosphates and release of IP3-sensitive calcium stores. Other DHPs also caused a release of calcium stores, but usually at significantly higher concentrations than those required for the inhibition of capacitative calcium influx. Certain DHPs appeared to cause an incomplete blockade of SOC channel-dependent elevations of calcium, suggesting the presence of more than one class of such channels in HL-60 cells. N-Methylnitrendipine (IC50 2.6 muM, MRS 1844) and N-propargylnifrendipine (IC50 1.7 muM, MRS 1845) represent possible lead compounds for the development of selective SOC channel inhibitors. Published by Elsevier Science Inc.
• Synthesis and pharmacological activity of furo-1,4-dihydropyridines
  作者：I. P. Skrastin'sh、V. V. Kastron、R. O. Vitolin'、G. Ya. Dubur、M. I. Stivrinya、K. A. Kaidaka

  DOI：10.1007/bf00764614

  日期：1989.11
• Synthesis and pharmacological activity of 4-aryl-l,4-dihydropyridines
  作者：V. V. Kastron、G. Ya. Dubur、R. O. Vitolin'、A. A. Kimenis、M. Ya. Selga、N. V. Kondratenko、L. M. Yagupol'skii、D. Ya. Tirzite、Yu. A. Fialkov、S. V. Shelezhenko

  DOI：10.1007/bf00770311

  日期：1982.11
• Hantzsch 1,2,3,4-tetrahydropyridines related to calcium antagonists. Two synthetic approaches.
  作者：David A. Claremon、Steven D. Young

  DOI：10.1016/s0040-4039(00)98223-6

  日期：1985.1