2,6-dimethyl-3,5-diisopropoxycarbonyl-4-phenyl-pyridine | 88258-15-5

• 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: 2,6-dimethyl-3,5-diisopropoxycarbonyl-4-phenyl-pyridine
• 英文别名: Dipropan-2-yl 2,6-dimethyl-4-phenylpyridine-3,5-dicarboxylate
• CAS: 88258-15-5
• 化学式: C₂₁H₂₅NO₄
• 分子量: 355.434
• InChiKey: CMMONRZQCRBWBC-UHFFFAOYSA-N

物化性质

• 熔点：
  84.0-89.0 °C(Solv: isopropyl ether (108-20-3))
• 沸点：
  437.5±45.0 °C(Predicted)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  diisopropyl 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate 在 urea-hydrogen peroxide 、 碘 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 以93%的产率得到2,6-dimethyl-3,5-diisopropoxycarbonyl-4-phenyl-pyridine
  参考文献：
  名称：

  分子碘催化尿素-过氧化氢加合物对Hantzsch-1,4-二氢吡啶进行高效，无金属的室温芳构化

  摘要：

  开发了一种温和，高效，无金属的合成方法，该方法以20 mol％的分子碘为催化剂，使用脲-过氧化氢加合物作为氧化剂进行1,4-二氢吡啶的芳构化。该反应在室温下在乙酸乙酯中进行，并且以高至优异的产率分离出产物。基于在1，4-二氢吡啶环中具有烷基和芳基取代基的衍生物所获得的结果，提出了一种可能的自由基机理。

  DOI：

  10.1016/j.tet.2008.04.040

文献信息

• Oxidative aromatization of 1,4-dihydropyridines and pyrazolines using HbA–H2O2: An efficient biomimetic catalyst system providing metabolites of drug candidates
  作者：Atul Kumar、Ram Awatar Maurya、Siddharth Sharma

  DOI：10.1016/j.bmcl.2009.05.056

  日期：2009.8

  Human hemoglobin (HbA) efficiently catalyses the oxidative aromatization of 1,4-dihydropyridines (1,4-DHPs) and pyrazolines with hydrogen peroxide in phosphate buffer. The results of the study reveal that the rates of oxidative aromatization of 1,4-DHPs are substituent dependent. Thus, the present study is very useful in understanding the metabolism of 1,4-DHP drugs in liver by cytochrome P450 and designing novel drugs as well as modifying the existing drugs for better pharmacokinetic profile. (C) 2009 Elsevier Ltd. All rights reserved.
• A highly efficient biomimetic aromatization of Hantzsch-1,4-dihydropyridines with t-butylhydroperoxide, catalysed by iron(III) phthalocyanine chloride
  作者：Mirela Filipan-Litvić、Mladen Litvić、Vladimir Vinković

  DOI：10.1016/j.bmc.2008.09.004

  日期：2008.10

  Rapid aromatization of Hantzsch-1,4-DHPswith t-butylhydroperoxide catalysed by iron(III) phthalocyanine chloride is described. The reaction proceeds smoothly at room temperature within 1-35 min and the products of high purity were isolated in excellent yields. To explain the reactivity of this catalytical system plausible mechanism have been proposed to involve formation of high-valent oxoferryl species as in cytochrome P450 itself. (C) 2008 Elsevier Ltd. All rights reserved.
• US4497821A
  申请人：——

  公开号：US4497821A

  公开（公告）日：1985-02-05