methyl 2,6-bis(4-chlorophenyl)-1-(4-bromophenyl)-4-(4-bromophenylamino)-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 2,6-bis(4-chlorophenyl)-1-(4-bromophenyl)-4-(4-bromophenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate
• 英文别名: methyl (2S,6R)-4-(4-bromoanilino)-1-(4-bromophenyl)-2,6-bis(4-chlorophenyl)-3,6-dihydro-2H-pyridine-5-carboxylate
• 化学式: C₃₁H₂₄Br₂Cl₂N₂O₂
• 分子量: 687.258
• InChiKey: BKWIEBMTFUKWGR-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-氯苯甲醛 、 乙酰乙酸甲酯 、 4-溴苯胺 在 phosphotungstic acid 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以88%的产率得到methyl 2,6-bis(4-chlorophenyl)-1-(4-bromophenyl)-4-(4-bromophenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate
  参考文献：
  名称：

  H₃PW₁₂O₄₀-Catalyzed Multicomponent Reaction for Efficient Synthesis of Highly Substituted Piperidines

  摘要：

  以 H3PW12O40 为催化剂，通过 β 酮酯、芳香醛和苯胺的缩合合成高官能度哌啶的简单、非对映选择性、廉价和高效的路线被描述出来。反应完成后，催化剂可以很容易地回收并重复使用，而其活性不会发生很大变化。此外，在大多数情况下，哌啶会从溶液中析出。

  DOI：

  10.2174/1386207316666131229132950

文献信息

• Y(NO₃)₃·4H₂O-assisted Three-component Synthesis of Polysubstituted Tetrahydropyridines
  作者：Mir Rasul Mousavi、Jasem Aboonajmi、Malek Taher Maghsoodlou、Nourallah Hazeri

  DOI：10.3184/174751914x13890195583234

  日期：2014.2

  A mild and efficient method for the synthesis of polysubstituted tetrahydropyridines has been developed which involves a three-component reaction of an arylamine (2 equiv.), an araldehyde (2 equiv.) and ethyl (or methyl) acetoacetate (1 equiv.) in MeCN under ambient conditions, in the presence of yttrium nitrate, Y(NO₃)₃·4H₂O. This appears to be the first time yttrium nitrate has been used as a catalyst for this type of synthesis of tetrahydropyridines.

  在硝酸钇（Y(NO3)3-4H2O）存在的条件下，在 MeCN 中进行芳胺（2 等份）、芳醛（2 等份）和乙酰乙酸乙酯（或乙酰乙酸甲酯）（1 等份）的三组分反应。这似乎是首次使用硝酸钇作为催化剂合成四氢吡啶类化合物。
• Cerium(IV) triflate-catalyzed domino annulation approaches to the synthesis of highly substituted piperidines
  作者：Samad Khaksar、Seyed Mohammad Vahdat、Mandana Alipour

  DOI：10.1016/j.crci.2013.03.011

  日期：2013.11

  Résumé A simple, diastereoselective, inexpensive, and efficient route for the synthesis of highly functionalized piperidines by the condensation of β-keto-esters, aromatic aldehydes and anilines using cerium(IV) triflate as a catalyst is described. In most cases, the piperidine precipitates out of the solution.

  简述了以三(IV)铈为催化剂，通过缩合β-酮酯、芳香醛和苯胺合成高官能度哌啶的一条简单、非对映选择性、廉价且高效的路线。在大多数情况下，哌啶会从溶液中析出。
• H<sub>3</sub>PW<sub>12</sub>O<sub>40</sub>-Catalyzed Multicomponent Reaction for Efficient Synthesis of Highly Substituted Piperidines
  作者：Samad Khaksar、Seyed Baghbanian、Nastaran Barsan

  DOI：10.2174/1386207316666131229132950

  日期：2013.12.29

  A simple, diastereoselective, inexpensive, and efficient route for the synthesis of highly functionalized piperidines by the condensation of β-keto-esters, aromatic aldehydes and anilines using H3PW12O40 as a catalyst is described. The catalyst could be easily recovered after completion of the reaction and reused without a considerable change in its activity. Furthermore, in most cases the piperidine precipitates out of solution.

  以 H3PW12O40 为催化剂，通过 β 酮酯、芳香醛和苯胺的缩合合成高官能度哌啶的简单、非对映选择性、廉价和高效的路线被描述出来。反应完成后，催化剂可以很容易地回收并重复使用，而其活性不会发生很大变化。此外，在大多数情况下，哌啶会从溶液中析出。
• La(NO<sub>3</sub>)<sub>3</sub>.6H<sub>2</sub>O Catalyzed One-pot Highly Diastereoselective Synthesis of Functionalized Piperidines
  作者：Mir Rasul Mousavi、Jasem Aboonajmi、Malek Taher Maghsoodlou、Nourallah Hazeri、Sayyed Mostafa Habibi-Khorassani、Mohyeddin Safarzaei

  DOI：10.2174/1570178611310030005

  日期：2013.4.1

  La(NO3)3.6H2O was used as an efficient catalyst for highly diastereoselective synthesis of functionalized piperidines by one-pot five-component reactions of anilines and aromatic aldehydes with acetoacetic esters. This strategy proceeds by way of the Knoevenagel reaction followed by inter-molecular aza-Diels-Alder reaction. The main features of the current method comprise mild reaction conditions,

  La（NO 3）3 .6H 2 O被用作通过苯胺和芳族醛与乙酰乙酸酯的一锅五组分反应高度非对映选择性合成官能化哌啶的有效催化剂。该策略通过Knoevenagel反应进行，随后进行分子间氮杂-Diels-Alder反应。当前方法的主要特点是反应条件温和，后处理容易，生态友好，原子经济性高，时间短，并且分离出的产物产率高。
• Organocatalytic asymmetric multicomponent reactions of aromatic aldehydes and anilines with β-ketoesters: facile and atom-economical access to chiral tetrahydropyridines
  作者：Xuejian Li、Yanyan Zhao、Haijun Qu、Zhenjun Mao、Xufeng Lin

  DOI：10.1039/c2cc38349g

  日期：——

  The first catalytic asymmetric pseudo five-component (AB(2)C(2) type) reaction is reported. A spirocyclic chiral phosphoric acid catalyzed one-pot multicomponent reaction of aromatic aldehydes, anilines and beta-ketoesters and afforded highly functionalized enantioenriched tetrahydropyridines with high levels of stereocontrol.

  报告了第一个催化不对称拟五组分（AB（2）C（2）型）反应。螺环手性磷酸催化芳族醛，苯胺和β-酮酸酯的一锅多组分反应，并提供高度官能化的对映体富集的四氢吡啶，具有高水平的立体控制。