diethyl 4-(4-hydroxyphenyl)-2,6-dimethyl-3,5-pyridinedicarboxylate | 81014-98-4

• 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: diethyl 4-(4-hydroxyphenyl)-2,6-dimethyl-3,5-pyridinedicarboxylate
• 英文别名: diethyl 4-(4-hydroxyphenyl)-2,6-dimethylpyridine-3,5-dicarboxylate；Diethyl 4-(4-hydroxyphenyl)-2,6-dimethylpyridine-3,5-dicarboxylate
• CAS: 81014-98-4
• 化学式: C₁₉H₂₁NO₅
• 分子量: 343.379
• InChiKey: CPUHFNXAASGWCL-UHFFFAOYSA-N

物化性质

• 熔点：
  174-176 °C
• 沸点：
  452.9±45.0 °C(Predicted)
• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  85.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 4-(4-hydroxyphenyl)-2,6-dimethyl-3,5-pyridinedicarboxylate 在 bismuth(III) nitrate 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以70%的产率得到4-(4-Hydroxy-3-nitro-phenyl)-2,6-dimethyl-pyridine-3,5-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Bismuth Nitrate Pentahydrate: A Convenient Reagent for the Oxidation of Hantzsch 1,4-Dihydropyridines

  摘要：

  DOI：

  10.1055/s-1998-4516
• 作为产物：
  描述：

  4-(4-hydroxy-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester 在 叔丁基过氧化氢 、 sodium dithionite 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 6.0h， 以83%的产率得到diethyl 4-(4-hydroxyphenyl)-2,6-dimethyl-3,5-pyridinedicarboxylate
  参考文献：
  名称：

  A new oxidation system for the oxidation of Hantzsch-1,4-dihydropyridines and polyhydroquinoline derivatives under mild conditions

  摘要：

  已开发出一种氧化系统，通过氧化1,4-二氢吡啶和多羟基喹啉衍生物，可以高产率合成吡啶衍生物。

  DOI：

  10.1039/c5ra20977c

文献信息

• Certain antihypertensive 1-[2-[3-carbamoyl-4-hydroxy phenoxy]alkylene
  申请人：Ciba-Geigy Corporation

  公开号：US04559354A1

  公开（公告）日：1985-12-17

  The invention relates to novel substituted phenyl ethers of the formula ##STR1## in which Ar represents a mono- or bi-cyclic carbocyclic aryl radical, or a mono- or bi-cyclic heterocyclic aryl radical bonded to a phenylene radical by way of a ring carbon atom, Ph represents a phenylene radical, n has the value 0 to 1 and alk represents alkylene having from 2 to 5 carbon atoms, the nitrogen atom and the oxygen atom or, if n is 0, the aromatic radical being separated from each other by at least two carbon atoms in the unbranched chain, and R.sub.1 and R.sub.2 each represents, independently of the other, hydrogen or lower alkyl, or together represent lower alkylene, oxa-lower alkylene, thia-lower alkylene, aza-lower alkylene or N-lower alkyl-aza-lower alkylene, and salts thereof, especially pharmaceutically acceptable non-toxic acid addition salts. Such compounds possess, on the one hand, blocking properties towards .beta.-adrenergic receptors and can therefore be used as .beta.-receptor-blockers with or without cardioselectivity for the treatment of Angina pectoris, hypertrophic cardiomyopathy and heart rhythm disorders and also as blood-pressure-reducing agents. On the other hand, such compounds possess .beta.-receptor-stimulating properties and can therefore be used as positively inotropically active agents, especially as cardiotonics, for the treatment of heart muscle insufficiency.

  该发明涉及新型取代苯醚化合物，其化学式为##STR1##其中Ar代表单环或双环碳环芳基，或通过环碳原子与苯基相连的单环或双环杂环芳基，Ph代表苯基，n取值为0至1，alk代表具有2至5个碳原子的烷基，氮原子和氧原子或者如果n为0，则芳基在直链中至少被至少两个碳原子分隔，R.sub.1和R.sub.2分别独立地代表氢或低烷基，或者一起代表低烷基，氧杂低烷基，硫杂低烷基，氮杂低烷基或N-低烷基-氮杂低烷基，以及其盐，特别是药学上可接受的无毒酸盐。这类化合物一方面具有对β-肾上腺素受体的阻滞作用，因此可用作具有或不具有心脏选择性的β-受体阻滞剂，用于治疗心绞痛、肥厚型心肌病和心律失常，也可用作降压药。另一方面，这类化合物具有β-受体激动作用，因此可用作具有正肌力作用的药剂，特别是作为心力衰竭的治疗药物。
• Facile Aromatisation of Hantzsch 1,4-Dihydropyridines by Autoxidation in the Presence of <i>P</i>-toluenesulfonic Acid in Acetic Acid
  作者：Ding Zhang、Min Sha

  DOI：10.3184/174751918x15208600846791

  日期：2018.3

  A simple protocol to achieve the aromatisation of Hantzsch dihydropyridines in high yield was established using p-toluenesulfonic acid in acetic acid and yields of 90% were obtained at room temperature. With regards to the Hantzsch 1,4-dihydropyridines derived from alkyl aldehydes bearing one or more á-hydrogens, dealkylation products were obtained through a proposed autoxidation mechanism.

  使用乙酸中的对甲苯磺酸建立了以高产率实现 Hantzsch 二氢吡啶芳构化的简单方案，并且在室温下获得了 90% 的产率。对于衍生自带有一个或多个 α-氢的烷基醛的 Hantzsch 1,4-二氢吡啶，通过提出的自氧化机制获得了脱烷基产物。
• Silica-supported ceric ammonium nitrate (CAN): a simple, mild and solid-supported reagent for quickest oxidative aromatization of Hantzsch 1,4-dihydropyridines
  作者：Parvin Kumar、Kulbir Kadyan、Meenakshi Duhan、Jayant Sindhu、Khalid Hussain、Sohan Lal

  DOI：10.1007/s11696-018-0666-5

  日期：2019.5

  An efficient and environmentally benign methodology for the oxidative aromatization of 1,4-dihydropyridines to their corresponding pyridine derivatives is developed. The oxidative aromatization of 1,4-dihydropyridines was explored using silica-supported ceric ammonium nitrate as catalyst in CH3CN with or without sonication at room temperature. This supported catalyst acts as a more efficient oxidising

  开发了一种有效和环境友好的方法，用于将1，4-二氢吡啶氧化成相应的吡啶衍生物。使用二氧化硅负载的硝酸铈铈铵作为催化剂在CH 3 CN中进行室温或不超声处理，探索了1,4-二氢吡啶的氧化芳构化作用。这种负载型催化剂起着更有效的氧化剂的作用，并且在反应时间和收率方面都比其他报道的试剂更具优势。与不支持的形式相比，发现支持的试剂更有效和更具选择性。在本反应中未观察到Belousov–Zhabotinskii反应。在4-正烷基/ n情况下观察到的脱烷基在当前情况下也未观察到-烯基与其他氧化剂的结合。
• Aromatization of Hantzsch 1,4-Dihydropyridines with I2-MeOH
  作者：Jhillu S. Yadav、Basi V. Subba Reddy、Gowravaram Sabitha、Garudammagari S. Kiran Kumar Reddy

  DOI：10.1055/s-2000-7613

  日期：——

  4-Alkyl or aryl substituted Hantzsch 1,4-dihydropyridines are aromatized to the corresponding pyridines in high yields by iodine in refluxing methanol. The method tolerates several substituents such as alkyl, benzyl, aryl and heterocyclic groups present in the 4-position of pyridines.

  4-烷基或芳基取代的 Hantzsch 1,4-二氢吡啶通过碘在回流甲醇中以高产率芳构化为相应的吡啶。该方法容许存在于吡啶的 4 位上的几个取代基，例如烷基、苄基、芳基和杂环基团。
• Oxidative aromatization of Hantzsch 1,4-dihydropyridines by sodium chlorite
  作者：Xiali Liao、Wenbin Lin、Jun Lu、Chun Wang

  DOI：10.1016/j.tetlet.2010.05.091

  日期：2010.7

  Hantzsch 1,4-dihydropyridines were converted to the corresponding pyridines efficiently by sodium chlorite under mild conditions in excellent yields.

  在温和的条件下，亚氯酸钠可有效地将Hantzsch 1,4-二氢吡啶有效转化为相应的吡啶，并具有优异的收率。