methyl 4-(4-bromophenylamino)-1-(4-bromophenyl)-1,2,5,6-tetrahydro-2,6-bis(4-methoxyphenyl)pyridine-3-carboxylate | 1130969-65-1

• 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-bromophenylamino)-1-(4-bromophenyl)-1,2,5,6-tetrahydro-2,6-bis(4-methoxyphenyl)pyridine-3-carboxylate
• 英文别名: methyl 1-(4-bromophenyl)-4-(4-bromophenylamino)-2,6-bis(4-methoxyphenyl)-1,2,5,6-tetrahydropyridine-3-carboxylate；Methyl 1-(4-bromophenyl)-4-((4-bromophenyl)amino)-2,6-bis(4-methoxyphenyl)-1,2,5,6-tetrahydropyridine-3-carboxylate；methyl 4-(4-bromoanilino)-1-(4-bromophenyl)-2,6-bis(4-methoxyphenyl)-3,6-dihydro-2H-pyridine-5-carboxylate
• CAS: 1130969-65-1
• 化学式: C₃₃H₃₀Br₂N₂O₄
• 分子量: 678.42
• InChiKey: OLHQFUFHPLFADP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  60
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 乙酰乙酸甲酯 、 4-溴苯胺 在 ammonium cerium (IV) nitrate 作用下， 以 乙腈 为溶剂， 反应 21.0h， 以68%的产率得到methyl 4-(4-bromophenylamino)-1-(4-bromophenyl)-1,2,5,6-tetrahydro-2,6-bis(4-methoxyphenyl)pyridine-3-carboxylate
  参考文献：
  名称：

  硝酸铈铵催化的多组分反应有效合成功能化四氢吡啶

  摘要：

  据报道，在催化量的硝酸铈铵（CAN）存在下，β-酮酸酯，两当量的芳族醛和两当量的胺的多组分缩合反应可实现原子经济的一锅法合成功能化四氢吡啶。 。以这种方式，在室温下以中等至良好的产率获得了一系列药理学上有趣的取代的哌啶衍生物。

  DOI：

  10.1021/co100055x

文献信息

• An efficient one-pot multi-component synthesis of highly functionalized piperidines
  作者：Santosh V. Goswami、Prashant B. Thorat、Sudhakar R. Bhusare

  DOI：10.1515/hc-2012-0105

  日期：2012.12.1

  Abstract A simple, inexpensive and efficient one-pot synthesis of piperidine derivatives was achieved in excellent yield via the three-component reaction of substituted aniline, 1,3-dicarbonyl compound and aromatic aldehyde using phenylboronic acid as catalyst.

  摘要 以苯基硼酸为催化剂，通过取代苯胺、1,3-二羰基化合物和芳香醛的三组分反应，以优异的收率实现了简单、廉价、高效的哌啶衍生物一锅法合成。
• Fe(NO₃)₃·9H₂O as Efficient Catalyst for One-pot Synthesis of Highly Functionalized Piperidines
  作者：Nourallah Hazeri、Malek Taher Maghsoodlou、Sayyed Mostafa Habibi-Khorassani、Jasem Aboonajmi、Seyed Sajad Sajadikhah

  DOI：10.1002/jccs.201200421

  日期：2013.4

  Fe(NO3)3·9H2O is used as an efficient and effective catalyst for the one‐pot three‐component synthesis of highly functionalized piperidines from aromatic aldehydes, anilines and b–ketoesters in ethanol at ambient temperature. This procedure includes some important aspects like the easy work‐up, no need to column chromatography, simple and readily available precursors, and good to high yields.

  Fe（NO 3）3 ·9H 2 O可作为一种有效的催化剂，用于在环境温度下由芳族醛，苯胺和b-酮酸酯在乙醇中一锅三组分合成高度官能化的哌啶。该程序包括一些重要方面，例如易于处理，无需柱色谱，简单易用的前体以及良好到高收率。
• Photocatalytic activity of Rose Bengal encapsulated in zeolitic imidazolate framework-8 (RB@ZIF-8): an innovative approach for the one pot synthesis of highly functionalized tetrahydropyridines and study of their anti-tubercular activity
  作者：Munmee Goswami、Pooja Paul、Chayan Pandya、Ridahunlang Nongkhlaw、Arup Dutta、Jyothi Kumari、Dharmarajan Sriram、Akella Sivaramakrishna、Rishanlang Nongkhlaw

  DOI：10.1039/d4cy00218k

  日期：——

  By exploring the photocatalytic activity of Rose Bengal (RB) encapsulated in zeolitic imidazolate framework-8 (ZIF-8) under visible light irradiation, we developed a unique approach for the synthesis of highly functionalized tetrahydropyridines at ambient temperature. This protocol shows generality across various types of benzaldehydes, anilines and alkyl acetoacetates. Feasible operation, availability

  通过探索可见光照射下封装在咪唑骨架-8（ZIF-8）沸石中的孟加拉红（RB）的光催化活性，我们开发了一种在环境温度下合成高功能化四氢吡啶的独特方法。该方案显示了各种类型的苯甲醛、苯胺和乙酰乙酸烷基酯的通用性。该方法具有操作可行、起始原料易得、免柱层析纯化、反应时间短、废物产生量低、产品多样性高、TON和TOF高等特点。合成化合物的体外抗结核研究表明，化合物5t在所有合成衍生物中显示出最高的活性。
• Organocatalyzed highly atom economic one pot synthesis of tetrahydropyridines as antimalarials
  作者：Mridul Misra、Swaroop Kumar Pandey、Vivek Parashar Pandey、Jyoti Pandey、Renu Tripathi、Rama Pati Tripathi

  DOI：10.1016/j.bmc.2008.11.062

  日期：2009.1

  A highly atom economic one pot synthesis of tetrahydropyridines was achieved by L-proline/TFA catalysed multicomponent reaction of beta-keto-esters, aromatic aldehydes and anilines. The synthesized compounds were screened against Plasmodium falciparum in vitro and one of them showed antimalarial activity with MIC as low as 0.09 mu g/mL. (C) 2008 Elsevier Ltd. All rights reserved.