dimethyl 4-(2,4-dichlorophenyl)-1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate | 77233-94-4

• 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: dimethyl 4-(2,4-dichlorophenyl)-1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate
• 英文别名: 4-(2,4-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-bis(methoxycarbonyl)；dimethyl 4-(2,4-dichlorophenyl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate；3,5-Dimethyl 4-(2,4-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate；dimethyl 4-(2,4-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 77233-94-4
• 化学式: C₁₇H₁₇Cl₂NO₄
• mdl: MFCD00387791
• 分子量: 370.232
• InChiKey: FFQZJXYLJQZVPJ-UHFFFAOYSA-N

物化性质

• 熔点：
  190-192.5 °C(Solv: methanol (67-56-1))
• 沸点：
  458.6±45.0 °C(Predicted)
• 密度：
  1.302±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl 4-(2,4-dichlorophenyl)-1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 以80%的产率得到1H,3H-Difuro(3,4-b:3',4'-e)pyridine-1,7(4H)-dione, 5,8-dihydro-8-(2,4-dichlorophenyl)-
  参考文献：
  名称：

  Cardiovascular activity of difuropyridines

  摘要：

  DOI：

  10.1007/bf00772904
• 作为产物：
  描述：

  2,4-二氯苯甲醛 、 乙酰乙酸甲酯 在 Er(BTC)(H₂O)·(DMF)_1.1 、 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以75%的产率得到dimethyl 4-(2,4-dichlorophenyl)-1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate
  参考文献：
  名称：

  铒-有机骨架作为多相路易斯酸催化 Hantzsch 偶联和四氢-4H-Chromene 合成

  摘要：

  通过水热反应制备了铒-有机骨架。通过傅里叶变换红外光谱（FT-IR）、扫描电子显微镜（SEM）和X射线粉末衍射（XRD）对制备的骨架进行表征。该框架在 Er(III) 中心具有开放的金属位点，从而为亲电试剂活化提供了一个可接近的路易斯酸中心。因此，合成的骨架被用作 Hantzsch 偶联反应和四氢-4H-色烯合成的路易斯酸多相催化剂。通过改变反应时间、温度、溶剂和催化剂浓度来优化反应条件。合成了多种四氢-4H-色烯，并通过FT-IR 和1H NMR 光谱对其进行了表征。Er-MOF，作为路易斯酸多相催化剂，

  DOI：

  10.1007/s10562-016-1913-4

文献信息

• Synthesis of Substituted 1,4‐Dihydropyridines in Water Using Phase‐Transfer Catalyst Under Microwave Irradiation
  作者：Hojatollah Salehi、Qing‐Xiang Guo

  DOI：10.1081/scc-200039409

  日期：2004.12.31

  Abstract The synthesis of various substituted 1,4‐dihydropyridines has been achieved by the reaction of aldehydes, ethyl/methyl acetoacetates, and ammonium acetate in water using phase‐transfer catalyst under microwave irradiation. Compared to the classical Hantzsch's reaction conditions, this new method consistently has the advantage of good yields and short reaction times. Bifunctional compounds containing

  摘要 在微波辐射下，使用相转移催化剂，醛、乙酰乙酸乙酯和乙酸铵在水中反应合成了各种取代的 1,4-二氢吡啶。与经典的 Hantzsch 反应条件相比，这种新方法始终具有收率好和反应时间短的优点。已经使用二醛作为前体以良好的产率合成了含有两个单元的双功能化合物。
• Mannich reaction of dihydropyridine derivatives I. Reactions with secondary amines.
  作者：JIRO ARITOMI、SHOZO UEDA、HARUKI NISHIMURA

  DOI：10.1248/cpb.28.3163

  日期：——

  Dialkyl 4-aryl-1, 4-dihydro-2, 6-dimethylpyridine-3, 5-dicarboxylates (III) were subjected to the Mannich reaction with excess paraformaldehyde and secondary amine hydrochloride in boiling ethanolic solution. When the compounds III were treated with a 5-to 7-fold molar excess of the aldehyde and amine salt, 2, 6-bis (2-disubstituted aminoethyl)-dihydropyridine derivatives (V) were obtained in good yields. On treatment with a 2- to 3-fold molar excess of the reactants, compounds III were converted to 2-(2-disubstituted aminoethyl)-6-methyldihydropyridine derivatives (IV) and V. When dioxane was used as a solvent with a 6-fold molar excess of the reactants, the tetrakis (dimethylaminomethyl) derivative (VII) was obtained.

  二烷基 4-芳基-1, 4-二氢-2, 6-二甲基吡啶-3, 5-二羧酸酯 (III) 在沸腾的乙醇溶液中与过量的多聚甲醛和二级胺盐酸盐进行曼尼希反应。当化合物 III经5-至7-倍摩尔过量的醛和胺盐处理时，可获得产率良好的 2, 6-双(2-二取代氨基乙基)-二氢吡啶衍生物 (V)。用2-至3-倍摩尔过量的反应物处理时，化合物 III 转化成 2-(2-二取代氨基乙基)-6-甲基二氢吡啶衍生物 (IV) 和 V。当使用二氧六环作为溶剂并采用6-倍摩尔过量的反应物时，得到四(二甲氨基甲基)衍生物 (VII)。
• Alginic acid: a highly efficient renewable and heterogeneous biopolymeric catalyst for one-pot synthesis of the Hantzsch 1,4-dihydropyridines
  作者：Mohammad G. Dekamin、Siamand Ilkhanizadeh、Zahra Latifidoost、Hamed Daemi、Zahra Karimi、Mehdi Barikani

  DOI：10.1039/c4ra11801d

  日期：——

  Alginic acid was found to be an efficient, environmentally benign, easily recoverable and low-cost catalyst for clean synthesis of 1,4-dihydropiridine derivatives (DHPs).

  发现海藻酸是一种高效、环境友好、易于回收和低成本的催化剂，可用于清洁合成1,4-二氢吡啶衍生物（DHPs）。
• Magnetic Fe3O4 nanoparticles: Efficient and recoverable nanocatalyst for the synthesis of polyhydroquinolines and Hantzsch 1,4-dihydropyridines under solvent-free conditions
  作者：Masoud Nasr-Esfahani、S. Jafar Hoseini、Morteza Montazerozohori、Rasool Mehrabi、Hasan Nasrabadi

  DOI：10.1016/j.molcata.2013.11.010

  日期：2014.2

  A green approach for efficient and rapid synthesis of biologically active substituted Hantzsch 1,4-dihydropyridine and polyhydroquinoline derivatives using magnetic Fe3O4 nanoparticles (Fe3O4 MNPs) as a recyclable catalyst under solvent-free conditions was reported. The catalyst was characterized by FT-IR, XRD, and TEM analysis. Compared to the classical reactions, this method consistently has the

  报道了在无溶剂条件下使用磁性Fe 3 O 4纳米颗粒（Fe 3 O 4 MNPs）作为可循环利用催化剂高效，快速合成生物活性取代的Hantzsch 1,4-二氢吡啶和聚氢喹啉衍生物的绿色方法。通过FT-IR，XRD和TEM分析对催化剂进行了表征。与经典反应相比，该方法始终具有反应时间短，催化剂负载少，收率高，易于磁分离和催化剂可重复使用的优点。
• Chiral Phosphoric Acid Catalyzed Enantioselective Desymmetrization of 1,4‐Dihydropyridines by C(sp ³ )−H Bromination
  作者：Min Han、Shi‐qi Zhang、Xin Cui、Qi‐wei Wang、Guang‐xun Li、Zhuo Tang

  DOI：10.1002/anie.202201418

  日期：2022.5.23

  used as substrates to obtain chiral Hantzsch-type 1,4-DHPs, which are frequently contained in pharmaceuticals. The inert C−H bond was converted into a versatile C−Br bond, which enabled the modification of the chiral 1,4-DHP derivatives with high efficiency by nucleophilic substitution. Furthermore, axially chiral 4-aryl pyridines were accessible by central-to-axial chirality conversion.

  容易获得的对称 1,4-二氢吡啶 (1,4-DHP) 被用作底物以获得药物中经常含有的手性 Hantzsch 型 1,4-DHP。惰性 C-H 键被转化为通用的 C-Br 键，从而能够通过亲核取代高效地修饰手性 1,4-DHP 衍生物。此外，轴向手性 4-芳基吡啶可通过中心到轴向手性转换获得。