diethyl 4-(4-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylate | 83301-14-8

• 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-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 83301-14-8
• 化学式: C₁₈H₂₁NO₅
• 分子量: 331.368
• InChiKey: PYNQZIAPEOTGMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 4-(4-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylate 生成 tetraethyl 6,12-bis(4-methoxyphenyl)-3,9-diazahexacyclo[6.4.0.0^2,7.0^4,11.0^5,10]dodecane-1,5,7,11-tetracarboxylate
  参考文献：
  名称：

  二聚体4-芳基-1,4-二氢吡啶的新型固态合成

  摘要：

  在固态辐射下，4-芳基-1,4-二氢吡啶1经历[2 + 2]环二酮至中心对称的头对尾二聚体3和4a。该笼二聚体几乎只形成3 经由与c 2 -对称顺-dimers 2发生在几乎定量的产率，在与所述的环加成反应对比度抗-dimer 4a中，这是伴随着光氧化，以吡啶5a中。

  DOI：

  10.1002/jhet.5570350217
• 作为产物：
  描述：

  (E)-3-<(triphenylphosphoranylidene)amino>propenoic acid ethyl ester 在 盐酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 24.5h， 生成 diethyl 4-(4-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Reaction of N-Vinylic Phosphazenes Derived from β-Amino Acids with Aldehydes. Azadiene-Mediated Synthesis of Dihydropyridines, Pyridines, and Polycyclic Nitrogen Derivatives

  摘要：

  Enamino phosphonium salts 2 are obtained by 1,2-addition of hydrogen chloride to N-vinylic phosphazenes 1 derived from triphenylphosphine. Aza-Wittig reaction of phosphazenes 1 derived from triphenylphosphine and 6 derived from diphenylmethylphosphine with aldehydes 3 leads to the formation of 2-azadienes 7. Reaction of azadienes 7 with enamines affords dihydropyridines 9 and 11, pyridines 12, and bicyclic nitrogen heterocycles 15-18 in a regioselective fashion, while heterodiene 20 reacts in the same way with pyrrolidinocyclohexanone giving 1-azaphenanthrene compound 21. Reaction of enamino phosphonium salts 2 with aldehydes 3 gives symmetrical dihydropyridines 5.

  DOI：

  10.1021/jo9902650

文献信息

• Synthesis of 1,4-Dihydropyridines and Their Fluorescence Properties
  作者：Shunsuke Sueki、Ryo Takei、Yuto Zaitsu、Junya Abe、Akane Fukuda、Keisuke Seto、Yukio Furukawa、Isao Shimizu

  DOI：10.1002/ejoc.201402426

  日期：2014.8

  We have successfully synthesized 3,4,5-substituted 1,4-dihydropyridines (1,4-DHPs) from amine hydrochloride salts, aldehydes, and acetals in good yields without the addition of a catalyst. The synthesized 1,4-DHPs exhibit various wavelengths of fluorescence, which could be tuned by changing the substituents at the 3- and 5-positions of the 1,4-DHPs.

  我们已经成功地从胺盐酸盐、醛和缩醛中合成了 3,4,5-取代的 1,4-二氢吡啶 (1,4-DHPs)，且收率良好，无需添加催化剂。合成的 1,4-DHPs 显示出不同波长的荧光，可以通过改变 1,4-DHPs 3-和 5-位的取代基来调节。
• Multicomponent Reactions for Diverse Synthesis of<i>N</i>-Substituted and NH 1,4-Dihydropyridines
  作者：Jieping Wan、Youyi Zhou、Yunyun Liu、Zheng Fang、Chengping Wen

  DOI：10.1002/cjoc.201300918

  日期：2014.3

  The multicomponent reactions of aldehydes, electron deficient alkynes and amines have been successfully performed to yield a number of symmetrical 2,6‐unsubstituted 1,4‐dihydropyridines (1,4‐DHPs). This method has been found generally applicable for the synthesis of both N‐substituted and N‐unsubstituted 1,4‐DHPs by employing secondary amine to activate the alkyne component via enaminoester intermediates

  醛，缺乏电子的炔烃和胺的多组分反应已成功进行，得到了许多对称的2,6-未取代的1,4-二氢吡啶（1,4-DHPs）。已经发现该方法通常可用于合成N-取代的和N-未取代的1,4-DHP，方法是使用仲胺通过烯胺酯中间体活化炔烃组分。本方法通过烯胺型活化进行，这不同于采用AcOH作为溶剂的已知方法。
• Unusual Reactivity of (Vinylimino)phosphoranes and Their Utility in the Preparation of Pyridine and Dihydropyridine Derivatives
  作者：Pedro Molina、Aurelia Pastor、María Jesús Vilaplana

  DOI：10.1021/jo960940v

  日期：1996.11.15

  New reactions of (vinylimino)phosphoranes with aldehydes involving an initial nucleophilic attack of the beta-carbon atom of the vinyl side chain on the carbonyl carbon atom are reported. Iminophosphorane 4 derived from ethyl beta-azidoacrylate reacts with substituted cinnamyl aldehydes to give a mixture of 2-arylpyridine and 4-styryldihydropyridine derivatives, whereas the reaction with substituted

  据报道，（乙烯基亚氨基）磷杂环戊烷与醛的新反应涉及乙烯基侧链的β-碳原子在羰基碳原子上的初始亲核攻击。衍生自β-叠氮丙烯酸乙酯的亚氨基磷烷4与取代的肉桂醛反应生成2-芳基吡啶和4-苯乙烯基二氢吡啶衍生物的混合物，而与取代的苯甲醛的反应提供4-芳基二氢吡啶衍生物。然而，衍生自叠氮富马酸二乙酯的亚氨基磷烷16通过预期的氮杂-维蒂希方式与肉桂醛反应，在所得二氢吡啶脱氢后得到4-芳基吡啶衍生物。
• Hetero-intermolecular [2+2] photocycloaddition of 1,4-dihydropyridines: a combined experimental and DFT study
  作者：Qiangwen Fan、Hongbo Tan、Peng Li、Hong Yan

  DOI：10.1039/c8nj02192a

  日期：——

  In this article, the hetero-intermolecular [2+2] photocycloaddition of 1,4-dihydropyridines (1,4-DHPs) in solution was reported, wherein head-to-tail (HT) dimeric products (syn-dimers and cage dimers) were formed exclusively through successive inter- and intra-molecular [2+2] cycloaddition. The effects of irradiation wavelength, solvents and substituents on the efficiency of these transformations were

  在本文中，在异质的分子间[2 + 2]的溶液中1,4-二氢吡啶（1,4-DHP类）光环被报道，其特征在于，头-尾（HT）的二聚产物（顺式-dimers和笼二聚体）仅通过连续的分子间和分子内[2 + 2]环加成反应形成。研究了辐照波长，溶剂和取代基对这些转化效率的影响。为了阐明光环加成反应的内在特征和立体选择性，进行了DFT和TDDFT理论计算，以揭示详细的反应过程。
• Highly regioselective photodimerization of 1,4-dihydropyridines: An efficient synthesis of novel 3,6-diazatetraasteranes
  作者：Hong-Bo Tan、Zhi-Chang Zhao、Zong-Shan Ma、Hong Yan

  DOI：10.1016/j.tet.2017.10.019

  日期：2018.2

  1,4-dihydropyridines does not afford novel head-to-head 3,6-diazatetraasteranes. Herein, we describe a highly regioselective method to synthesize 3,6-diazatetraasteranes via an intramolecular photodimerization of 1,4-dihydropyridines. First, the 1,4-dihydropyridines were tethered by phthaloyl to direct a proximate parallel arrangement in head-to-head orientation by the rotation of CC single bonds in

  传统的1，4-二氢吡啶的光环加成不能提供新颖的头对头的3，6-二氮杂四硬脂烷。在这里，我们描述了一种高度区域选择性的方法，通过1，4-二氢吡啶的分子内光二聚作用来合成3,6-二氮杂四环烷。首先，通过邻苯二甲酰基将1,4-二氢吡啶束缚在一起，以通过C的旋转在头对头方向上指导近似的平行排列溶液中的C单键。随后进行分子内[2 + 2]光环加成反应，以高收率（92–97％）和优异的区域选择性得到所需的3,6-二氮杂四硬脂烷。此外，两种不同的1,4-二氢吡啶也可以通过这种策略进行区域控制，并以简洁有效的方式通过交叉光二聚化产生多取代的3,6-二氮杂四硬脂烷。另外，该方法可以提供从1，4-二氢吡啶类似物直接进入其他多取代的多面体支架的途径。