methyl 4-(4-chlorophenylamino)-2,6-bis(4-bromophenyl)-1-(4-chlorophenyl)-1,2,5,6-tetrahydropyridine-3-carboxylate

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: methyl 4-(4-chlorophenylamino)-2,6-bis(4-bromophenyl)-1-(4-chlorophenyl)-1,2,5,6-tetrahydropyridine-3-carboxylate
• 英文别名: methyl 2,6-bis(4-bromophenyl)-1-(4-chlorophenyl)-4-((4-chlorophenyl)amino)-1,2,5,6-tetra hydropyridine-3-carboxylate；2,6-bis-(4-bromophenyl)-1-(4-chlorophenyl)-4-(4-chlorophenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester；methyl (2S,6R)-2,6-bis(4-bromophenyl)-4-(4-chloroanilino)-1-(4-chlorophenyl)-3,6-dihydro-2H-pyridine-5-carboxylate
• 化学式: C₃₁H₂₄Br₂Cl₂N₂O₂
• 分子量: 687.258
• InChiKey: MCQWTKATVXIWTF-MFMCTBQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-溴苄醇 在 叔丁基过氧化氢 作用下， 以 乙醇 为溶剂， 反应 5.17h， 生成 methyl 4-(4-chlorophenylamino)-2,6-bis(4-bromophenyl)-1-(4-chlorophenyl)-1,2,5,6-tetrahydropyridine-3-carboxylate
  参考文献：
  名称：

  磁性纤维素纳米纤维上坚固、高活性且稳定的负载 Co(II) 纳米颗粒，功能化用于哌啶和醇氧化的多组分反应

  摘要：

  通过将希夫碱配体扇区和纤维素纳米纤维吊带锚定在MNP（Fe 3 O 4 ）上，制备了新型可回收钴三核磁性催化剂，并将其命名为MNP@CNF@ATSM–Co( II )。另外，MNP 和 CNF 具有令人非常感兴趣的吸附特性。这样，该催化剂被设计用于在无溶剂条件下合成哌啶衍生物以及以EtOH为溶剂进行醇氧化反应。值得注意的是，该催化剂对环境安全，不需要外部碱。这种MNPs@CNF@ATSM–Co( II )可分离催化剂已经使用各种表征技术进行了评估，例如FT-IR、XRD、FE-SEM、EDX、EDS、ICP、TGA、DLS、HRTEM和VSM。该催化剂与多种苯甲醇、苯甲醛和胺衍生物相容，并产生了所有这些都引起足够兴趣的互补偶联产物。证明了Co（三核）在催化剂中的协同性能，并分别合成了MNPs、MNPs@CNF、MNPs@CNF@ATS–Co( II )和MNPs@CNF@ATSM–Co( II

  DOI：

  10.1039/d1ra00208b

文献信息

• Introduction of antimony triiodide (SbI3) as a new and efficient catalyst for synthesis of polyfunctionalized piperidines
  作者：Farhad Omarzehi Chahkamali、Mohammad Reza Faghihi、Malek Taher Maghsoodlou

  DOI：10.1007/s11164-016-2582-z

  日期：2016.12

  Abstract In the present work, an efficient and convenient one-pot multi-component reaction is reported for the synthesis of highly diversified piperidines by tandem condensation reaction of aromatic aldehydes, anilines, and β -keto esters in the presence of a catalytic amount (15 mol%) of SbI3 in EtOH at 50 °C. The advantages of this protocol are that it is easy to work up and inexpensive, the catalyst

  摘要本文 报道了在催化量存在下通过芳香醛，苯胺和 β- 酮酯的串联缩合反应合成高度多样化的哌啶的高效简便的单锅多组分反应方法 （15在50°C下在EtOH中的SbI 3（mol％）。该方案的优点是易于加工且廉价，催化剂和溶剂易于获得，并且产生了良好的产率。 图形概要
• Efficient one-pot synthesis of functionalized piperidine scaffolds via ZrOCl2·8H2O catalyzed tandem reactions of aromatic aldehydes with amines and acetoacetic esters
  作者：Sarita Mishra、Rina Ghosh

  DOI：10.1016/j.tetlet.2011.03.116

  日期：2011.6

  A highly efficient diastereoselective one-pot synthesis of functionalized piperidines has been developed based on an aqua-compatible ZrOCl2·8H2O catalyst via tandem reactions of aromatic aldehydes, amines, and acetoacetic esters.

  通过与水相容的ZrOCl 2 ·8H 2 O催化剂，通过芳族醛，胺和乙酰乙酸酯的串联反应，开发了一种高效的非对映选择性一锅合成的官能化哌啶。
• Trityl chloride as an efficient organic catalyst for one-pot, five-component and diastereoselective synthesis of highly substituted piperidines
  作者：Seyed Sajad Sajadikhah、Nourallah Hazeri、Malek Taher Maghsoodlou、Sayyed Mostafa Habibi-Khorassani、Anthony C. Willis

  DOI：10.1007/s11164-012-0997-8

  日期：2014.2

  chloride is used as an efficient organic catalyst for the one-pot, five-component and diastereoselective synthesis of highly substituted piperidines by means of reaction between aromatic aldehydes, amines and β -ketoesters in methanol at 50 °C. The structure as well as relative stereochemistry of products was confirmed by single X-ray crystallographic analysis. This homogeneous catalyst procedure includes

  摘要 三苯甲基氯是一种有效的有机催化剂，可通过芳香醛，胺和 β- 酮酸酯在甲醇中于50°C下反应，一锅，五组分和非对映选择性地合成高度取代的哌啶 。通过单X射线晶体分析证实了产物的结构以及相对立体化学。该均相催化剂程序包括一些重要方面，例如易于后处理，非对映选择性，简单易用的前体，廉价的催化剂，相对短的反应时间以及良好的高收率。 图形概要
• Silver, iron, and nickel immobilized on hydroxyapatite‐core‐shell γ‐Fe ₂ O ₃ MNPs catalyzed one‐pot five‐component reactions for the synthesis of tetrahydropyridines by tandem condensation of amines, aldehydes, and methyl acetoacetate
  作者：Sami Sajjadifar、Sobhan Rezayati、Azadeh Shahriari、Sima Abbaspour

  DOI：10.1002/aoc.4172

  日期：2018.3

  and Fe2+ immobilized on hydroxyapatite‐core‐shell γ‐Fe2O3 nanoparticles (γ‐Fe2O3@HAp‐Ag, γ‐Fe2O3@HAp‐Ni2+, and γ‐Fe2O3@HAp‐Fe2+) as a new and reusable Lewis acid magnetic nanocatalyst was successfully synthesized and reported for an atom economic, extremely facile, and environmentally benign procedure for the synthesis of highly functionalized tetrahydropyridines derivatives 4a‐t is described by one‐pot

  在这项研究中，银，镍2+和Fe 2+固定在羟基磷灰石的核-壳了γ-Fe 2 ö 3纳米颗粒（γ-的Fe 2 ö 3 @ HAP-AG，γ-的Fe 2 ö 3 @的HAp-Ni系2+，和γ -铁2 ö 3 @ HAP-的Fe 2+）作为一种新的和可重复使用的路易斯酸磁性纳米催化剂成功地合成和报告的原子经济，极其容易，并且对环境无害的程序高度官能化四氢吡啶的合成衍生物4a-t通过2个当量的醛1的单锅五组分反应来描述，在室温下在EtOH中有2个当量的胺2和1个当量的乙酰乙酸甲酯3，具有良好至高的收率和较短的反应时间。提出的方法具有许多优点，例如操作简便，磁性纳米催化剂的可重复使用性，操作简便，绿色合成避免了有毒的试剂和溶剂，温和的反应条件以及无需繁琐的色谱柱分离。
• First report of syn isomers in the diastereoselective synthesis of highly functionalized piperidines catalysed by wet picric acid: factors influencing the syn–anti ratios
  作者：Chhanda Mukhopadhyay、Sunil Rana、Ray J. Butcher、Ann Marie Schmiedekamp

  DOI：10.1016/j.tetlet.2011.08.140

  日期：2011.11

  This is the first report of the formation of a syn-diastereoisomer in the diastereoselective synthesis of highly functionalized piperidines catalysed by wet picric acid via a one-pot, step-economic condensation of aromatic aldehydes, 1,3-dicarbonyl compounds and aromatic amines. DFT calculation shows that anti isomers are more stable compared to the syn. The syn-anti ratio of the products depends on the temperature and the nature of substitution on both the aromatic aldehydes and aromatic amines. Conditions for getting pure anti and pure syn compounds have been studied. (C) 2011 Elsevier Ltd. All rights reserved.