dimethyl (Z)-N-(4-bromophenyl)aminofumarate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: dimethyl (Z)-N-(4-bromophenyl)aminofumarate
• 英文别名: dimethyl (Z)-2-(4-bromoanilino)but-2-enedioate
• 化学式: C₁₂H₁₂BrNO₄
• 分子量: 314.136
• InChiKey: VDCPYPXNSPMETG-YFHOEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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 (Z)-N-(4-bromophenyl)aminofumarate 在 polyphosphoric acid 作用下， 反应 1.0h， 以78%的产率得到6-溴-4-羟基喹啉-2-甲酸甲酯
  参考文献：
  名称：

  Synthesis of quinoline thioethers as novel small molecule enhancers of monoclonal antibody production in mammalian cell culture

  摘要：

  A small library of novel quinoline derivatives containing different thioether substituents at position 4 have been synthesized and screened in murine hybridoma cell culture for their ability to enhance monoclonal antibody (mAb) production. From this set of compounds, four compounds have been discovered that enhanced immunoglobulin G (IgG) titer over negative control cultures due to an increase in specific productivity. These results demonstrate the utility of using organic synthesis and parallel ligand screening methods to discover novel cell culture additives that may be useful for increasing mAb yield in industrial biomanufacturing processes. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.09.020
• 作为产物：
  描述：

  丁炔二酸二甲酯 、 4-溴苯胺 反应 0.15h， 以98%的产率得到dimethyl (Z)-N-(4-bromophenyl)aminofumarate
  参考文献：
  名称：

  Introduction of a clean and promising protocol for the synthesis of β-amino-acrylates and 1,4-benzoheterocycles: an emerging innovation

  摘要：

  提出了一种高效、优雅且简单的过程，用于合成β-氨基丙烯酸酯衍生物和一系列具有生物学及药物活性的苯并杂环化合物，条件极为温和。该方案为已知方法提供了一种有价值的替代方案，并将应用于绿色合成领域。产品的区域和立体化学性质通过红外光谱、核磁共振和单晶X射线分析得以确定。

  DOI：

  10.1039/c1gc15701a

文献信息

• [EN] HETEROCYCLIC COMPOUNDS AS CALCIUM SENSING RECEPTOR MODULATORS FOR THE TREATMENT OF HYPERPARATHYROIDISM, CHRONIC RENAL FAILURE AND CHRONIC KIDNEY DISEASE<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES EN TANT QUE MODULATEURS DES RÉCEPTEURS DE DÉTECTION DU CALCIUM POUR LE TRAITEMENT DE L'HYPERPARATHYROÏDIE, DE L'INSUFFISANCE RÉNALE CHRONIQUE ET DE LA NÉPHROPATHIE CHRONIQUE
  申请人：LUPIN LTD

  公开号：WO2015162538A1

  公开（公告）日：2015-10-29

  The invention relates to heterocyclic compounds of Formula (I) and their pharmaceutically acceptable salts, wherein the substituents are as described herein, and their pharmaceutical compositions for use in medicine for the treatment of diseases or disorders associated with the modulation of calcium sensing receptor modulators (CaSR), like e.g. hyperparathyroidism, chronic renal failure and chronic kidney disease and their complications.

  这项发明涉及式(I)的杂环化合物及其药学上可接受的盐，其中取代基如本文所述，并且它们的药物组合物用于医学上治疗与调节钙感受受体调节剂（CaSR）相关的疾病或紊乱，例如甲状旁腺功能亢进症、慢性肾功能衰竭和慢性肾病及其并发症。
• Oxidative free radical reactions of enamino esters
  作者：Che-Ping Chuang、Yi-Lung Wu

  DOI：10.1016/j.tet.2003.12.035

  日期：2004.2

  produced by the cerium(IV) ammonium nitrate (CAN) oxidation of β-dicarbonyl compounds undergo efficient addition to the C–C double bond of enamino esters. This CAN mediated free radical reaction between enamino esters and β-dicarbonyl compounds provides a novel method for the synthesis of highly substituted pyrroles. The direct CAN oxidation of β-enaminocinnamates gave the dimerization products effectively

  描述了烯氨基酯的氧化自由基反应。β-二羰基化合物的硝酸铈（IV）硝酸铈铵（CAN）氧化产生的亲电子碳中心基团经过有效地添加到烯氨基酯的C-C双键中。烯胺酸酯和β-二羰基化合物之间的CAN介导的自由基反应为合成高度取代的吡咯提供了一种新颖的方法。β-烯胺肉桂酸酯的直接CAN氧化有效地产生了二聚产物。
• Heterocyclization of functionalized heterocumulenes with C,N-, C,O-, and C,S-Binucleophiles: XI. Synthesis of dialkyl 2-oxo-3,6-diaryl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylates by cyclocondensation of 1-chlorobenzyl isocyanates with dialkyl anilinofumarates
  作者：M. V. Vovk、O. V. Kushnir、V. A. Sukach、I. F. Tsymbal

  DOI：10.1134/s1070428010050209

  日期：2010.5

  1-Chlorobenzyl isocyanates react with N-arylfumarates with the formation of dialkyl 2-oxo-3,6-diaryl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylates that on alkaline hydrolysis are converted into 6-alkoxycarbonyl-1,4-diaryl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acids. The condensation of 1-chloro-1-phenyl-2,2,2-trifluoroethyl isocyanate with N-arylfumarates results in dialkyl 6-oxo-2,3-diaryl-2-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylates.
• Introduction of a clean and promising protocol for the synthesis of β-amino-acrylates and 1,4-benzoheterocycles: an emerging innovation
  作者：Garima Choudhary、Rama Krishna Peddinti

  DOI：10.1039/c1gc15701a

  日期：——

  A highly efficient, elegant and simple procedure with exceptionally mild conditions has been proposed for the synthesis of β-amino-acrylate derivatives and an array of biologically and pharmaceutically active benzoheterocycles. The protocol offers a valuable alternative to known methods and will find applications in the field of green synthesis. The regio- and stereo-chemistry of the products were established by IR, NMR and single crystal X-ray analysis.

  提出了一种高效、优雅且简单的过程，用于合成β-氨基丙烯酸酯衍生物和一系列具有生物学及药物活性的苯并杂环化合物，条件极为温和。该方案为已知方法提供了一种有价值的替代方案，并将应用于绿色合成领域。产品的区域和立体化学性质通过红外光谱、核磁共振和单晶X射线分析得以确定。
• Synthesis of quinoline thioethers as novel small molecule enhancers of monoclonal antibody production in mammalian cell culture
  作者：Shahid A. Kazi、Geoffrey F. Kelso、Simon Harris、Reinhard I. Boysen、Jamil Chowdhury、Milton Hearn

  DOI：10.1016/j.tet.2010.09.020

  日期：2010.11

  A small library of novel quinoline derivatives containing different thioether substituents at position 4 have been synthesized and screened in murine hybridoma cell culture for their ability to enhance monoclonal antibody (mAb) production. From this set of compounds, four compounds have been discovered that enhanced immunoglobulin G (IgG) titer over negative control cultures due to an increase in specific productivity. These results demonstrate the utility of using organic synthesis and parallel ligand screening methods to discover novel cell culture additives that may be useful for increasing mAb yield in industrial biomanufacturing processes. (C) 2010 Elsevier Ltd. All rights reserved.