2,6-dimethyl-3,5-diethoxycarbonyl-4-(3-hydroxyphenyl)-1,4-dihydropyridine | 34148-68-0

• 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-diethoxycarbonyl-4-(3-hydroxyphenyl)-1,4-dihydropyridine
• 英文别名: diethyl 4-(3-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate；diethyl 2,6-dimethyl-4-(3-hydroxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 34148-68-0
• 化学式: C₁₉H₂₃NO₅
• mdl: MFCD00375879
• 分子量: 345.395
• InChiKey: YSZFCIOQLMLJEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,6-dimethyl-3,5-diethoxycarbonyl-4-(3-hydroxyphenyl)-1,4-dihydropyridine 在 chromium(VI) oxide 、 溶剂黄146 作用下， 生成 4-(3-acetoxy-phenyl)-2,6-dimethyl-pyridine-3,5-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Kahn et al., Journal of the Chemical Society, 1949, p. 2128,2133

  摘要：

  DOI：
• 作为产物：
  描述：

  3-氨基巴豆酸乙酯 、 间羟基苯甲醛 在 溶剂黄146 作用下， 反应 1.0h， 以85%的产率得到2,6-dimethyl-3,5-diethoxycarbonyl-4-(3-hydroxyphenyl)-1,4-dihydropyridine
  参考文献：
  名称：

  Synthesis of Some C‐3,4,5‐Substituted 2,6‐Dimethyl‐1,4‐dihydropyridines (4‐DHPs)

  摘要：

  DOI：

  10.1080/00397910701357007

文献信息

• USE OF COMPOSITIONS OBTAINED BY CALCINING PARTICULAR METAL-ACCUMULATING PLANTS FOR IMPLEMENTING CATALYTICAL REACTIONS
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE

  公开号：US20150376224A1

  公开（公告）日：2015-12-31

  The use of metal-accumulating plants for implementing chemical reactions especially catalytical reactions.

  金属积累植物用于实现化学反应，特别是催化反应的使用。
• The efficient synthesis of Hantzsch 1,4-dihydropyridines via metal-free oxidative C C coupling by HBr and DMSO
  作者：Narjes Rezaei、Parviz Rashidi Ranjbar

  DOI：10.1016/j.tetlet.2018.10.010

  日期：2018.11

  synthesis of Hantzsch 1,4-dihydropyridines through metal-free oxidative CC coupling process was described. The reaction between benzylic alcohols, 1,3-dicarbonyl compounds and ammonium hydroxide in the presence of HBr in DMSO at 75 °C led to afford 1,4-dihydropyridine in excellent yields. This protocol introduces the use of benzyl alcohols instead of aldehydes as a new modification of the Hantzsch reaction

  描述了一种通过无金属的氧化性C C偶联过程新型高效合成Hantzsch 1,4-二氢吡啶的方法。苄醇，1，3-二羰基化合物与氢氧化铵在HBr存在下于DMSO中于75°C进行反应，从而以极佳的收率得到1,4-二氢吡啶。该协议引入了使用苯甲醇代替醛作为Hantzsch反应的一种新方法。
• Synthesis of 3,4-dihydropyrimidin-2(1H)-ones and 1,4-dihydropyridines using ammonium carbonate in water
  作者：Fatemeh Tamaddon、Zahra Razmi、Abbas Ali Jafari

  DOI：10.1016/j.tetlet.2009.12.098

  日期：2010.2

  known and new 3,4-dihydropyrimidin-2(1H)-ones and 1,4-dihydropyridines are prepared efficiently via Biginelli and Hantzsch reactions using ammonium carbonate in water. Competition between Biginelli and Hantzsch reactions is observed with pyridine carbaldehydes. Using this methodology, Hantzsch esters are synthesized in higher yields and purities than with other procedures without the use of a catalyst

  通过Biginelli和Hantzsch反应，使用碳酸铵在水中有效地制备了各种已知的和新的3,4-二氢嘧啶-2（1 H）-酮和1,4-二氢吡啶。用吡啶甲醛观察到Biginelli反应和Hantzsch反应之间的竞争。使用这种方法，无需使用催化剂或有机溶剂，即可比其他方法以更高的收率和纯度合成汉茨酯。
• [Fesipmim]Cl as highly efficient and reusable catalyst for solventless synthesis of dihydropyridine derivatives through Hantzsch reaction
  作者：Akansha Agrwal、Virendra Kasana

  DOI：10.1007/s12039-020-01770-9

  日期：2020.12

  catalyst were measured by vibrating sample magnetometer (VSM). The efficiency of the [Fesipmim]Cl catalyst was checked by using it for the synthesis of different derivatives of dihydropyridine through Hantzsch reaction via a three-component coupling reaction of substituted benzaldehydes, ethyl/ methyl acetoacetate and ammonium acetate. The formation and structures of all the synthesized compounds were confirmed

  摘要 在本研究中，合成了磁性铁氧体纳米粒子（铁氧体NPs）并通过溶胶-凝胶法用二氧化硅（ferrite @ SiO 2 NPs）进行了包覆。然后，制备二氧化硅丙基甲基咪唑氯化物离子液体[Sipmim] Cl，并与上述制备的铁氧体@SiO 2 NPs连接，以合成铁氧体二氧化硅丙基甲基咪唑氯化物[Fesipmim] Cl催化剂。[Fesipmim] Cl催化剂的形成通过傅立叶变换红外（FT-IR）光谱分析确认。X射线衍射（XRD）分析证实了铁氧体NPs和铁氧体@SiO 2 NPs的结构。透射电子显微镜（TEM）证明成功形成了铁素体NP和铁素体@SiO 2NP。扫描电子显微镜（SEM）结果表明，铁氧体NPs，铁素体@SiO 2 NPs和[Fesipmim] Cl的形态发生了变化。通过振动样品磁力计（VSM）测量[Fesipmim] Cl催化剂的磁性。[Fesipmim] Cl催化剂的效率通过使用
• Synthesis of tricarbonylchromium complexes of 4-aryl-1,4-dihydropyridines
  作者：Adeleh Moshtaghi Zonouz、Mina Abkar Aras、Nasrin Abuali

  DOI：10.1007/s11243-013-9698-4

  日期：2013.4

  Tricarbonylchromium complexes of 4-aryl-1,4-dihydropyridines have been synthesized both under standard thermodynamic conditions using Cr(CO)6 and under milder complexation conditions using more labile [Cr(CO)3(NH3)3] and (η6-naphthalene)Cr(CO)3. Selective complexation of the Cr(CO)3 on the aryl ring in the presence of a 1,4-dihydropyridine ring was achieved.Graphical Abstract

  4-芳基-1,4-二氢吡啶的三羰基铬配合物已在使用 Cr(CO)6 的标准热力学条件下和使用更不稳定的 [Cr(CO)3(NH3)3] 和 (η6-naphthalene )Cr(CO)3。在 1,4-二氢吡啶环的存在下，实现了芳环上 Cr(CO)3 的选择性络合。