ethyl 2-{[(4-bromophenyl)amino]methylidene}-3-oxobutanoate | 100380-48-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2-{[(4-bromophenyl)amino]methylidene}-3-oxobutanoate
• 英文别名: ethyl 2-[(4-bromoanilino)methylidene]-3-oxobutanoate
• CAS: 100380-48-1
• 化学式: C₁₃H₁₄BrNO₃
• 分子量: 312.163
• InChiKey: AMDKTRJOEQYGRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-{[(4-bromophenyl)amino]methylidene}-3-oxobutanoate 在 三氯氧磷 作用下， 以 diphenyl ether-biphenyl eutectic 为溶剂， 反应 4.5h， 生成 1-(6-溴-4-氯喹啉-3-基)乙酮
  参考文献：
  名称：

  [EN] QUINOLINE DERIVATIVES AND MELK INHIBITORS CONTAINING THE SAME
  [FR] DÉRIVÉS DE QUINOLINE ET INHIBITEURS DE MELK LES CONTENANT

  摘要：

  本发明涉及一种由化学式（I）表示的化合物。

  公开号：

  WO2012016082A1
• 作为产物：
  描述：

  4-溴苯胺 、 2-乙氧亚甲基乙酰乙酸乙酯 反应 0.08h， 以65%的产率得到ethyl 2-{[(4-bromophenyl)amino]methylidene}-3-oxobutanoate
  参考文献：
  名称：

  Structural and theoretical studies of [6-bromo-1-(4-fluorophenylmethyl)-4(1H)-quinolinon-3-yl)]-4-hydroxy-2-oxo-3-butenoïc acid as HIV-1 integrase inhibitor

  摘要：

  Ethyl [6-bromo-1-(4-fluorophenylmethyl)-4(1H)-quinolinon-3-yl]-4-hydroxy-2-oxo-3-butenoate 1 and [6-bromo-1-(4-fluorophenylmethyl)-4(1H)-quinolinon-3-yl)]-4-hydroxy-2-oxo-3-buteno c acid 2 were synthesized as potential HIV-1 integrase inhibitors and evaluated for their enzymatic and antiviral activity, acidic compound 2 being more potent than ester compound 1. X-ray diffraction analyses and theoretical calculations show that the diketoacid chain of compound 2 is preferentially coplanar with the quinolinone ring (dihedral angle of 0-30 degrees). Docking studies suggest binding modes in agreement with structure-activity relationships. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.044

文献信息

• Silver-Catalyzed Cascade Reaction of β-Enaminones and Isocyanoacetates To Construct Functionalized Pyrroles
  作者：Guichun Fang、Jianquan Liu、Junkai Fu、Qun Liu、Xihe Bi

  DOI：10.1021/acs.orglett.7b00201

  日期：2017.3.17

  reported. In this reaction, tautomeric equilibria of β-enaminones are utilized to generate imine partners in situ. A hypothesized sequential Mannich addition/cyclization of imine tautomers and isocyanoacetates followed by an unprecedented ring-opening of the resultant 2-imidazolines and dehydration–condensation deliver the final 1,2,4,5-tetrasubstituted pyrrole products.

  报道了出乎意料的银催化的β-烯胺酮和异氰基乙酸酯的级联反应，提供了官能化的吡咯衍生物。在该反应中，利用β-烯胺酮的互变异构平衡原位产生亚胺配体。假设亚胺互变异构体和异氰基乙酸酯的顺序Mannich加成/环化反应，然后空前的所得2-咪唑啉开环和脱水缩合反应生成最终的1,2,4,5-四取代吡咯产物。
• Microwave Assisted Gould-Jacobs Reaction for Synthesis of 3-Acetyl-4-hydroxyquinoline Derivatives
  作者：Ashhar uz Zaman、Misbahul Ain Khan、Munawar Ali Munawar、Muhammad Makshoof Athar、Muhammad Pervaiz、Ansar Pervaiz、Ayaz Mahmood

  DOI：10.14233/ajchem.2015.18094

  日期：——

  Different types of quinoline derivatives have been synthesized by microwave irradiation and reaction yields were compared with reported classical methodology. The emphasis on this research project was to reduce reaction times and enhance the yields of the title compounds especially by using readily available materials including aryl amines. The key intermediate formed by condensation of microwave assisted multicomponent reaction under solvent free conditions was further cyclized through a heat mediated Gould-Jacobs cyclization reaction to get substituted quinolines. A study was also made to establish one pot synthesis of quinoline derivatives in order to eliminate the purification/drying step to get key intermediate but the product yields were found to be very poor than those in the classical methodology. The synthesized compounds were characterized and identified, using different spectroscopic tools i.e., FT-IR, mass spectrometry, elemental analysis and 1H NMR.

  通过微波辐射合成了不同类型的喹啉衍​​生物，并将反应产率与报道的经典方法进行了比较。该研究项目的重点是减少反应时间并提高标题化合物的产率，特别是通过使用包括芳基胺在内的现成材料。在无溶剂条件下微波辅助多组分反应缩合形成的关键中间体通过热介导的Gould-Jacobs环化反应进一步环化，得到取代的喹啉。还进行了一项研究，建立喹啉衍生物的一锅合成法，以消除纯化/干燥步骤以获得关键中间体，但发现产物收率比经典方法中的产物收率非常差。使用不同的光谱工具（即 FT-IR、质谱、元素分析和 1H NMR）对合成的化合物进行了表征和鉴定。
• QUINOLINE DERIVATIVES AND MELK INHIBITORS CONTAINING THE SAME
  申请人：Matsuo Yo

  公开号：US20130217671A1

  公开（公告）日：2013-08-22

  The present invention directs a compound represented by formula (I).

  本发明涉及一种由公式(I)所代表的化合物。
• Quinoline derivatives and MELK inhibitors containing the same
  申请人：Matsuo Yo

  公开号：US09120749B2

  公开（公告）日：2015-09-01

  The present invention directs a compound represented by formula (I).

  本发明涉及一种由式(I)所代表的化合物。
• Jaeger, E.-G.; Kirchhof, Barbara; Schmidt, E., Zeitschrift fur Anorganische und Allgemeine Chemie
  作者：Jaeger, E.-G.、Kirchhof, Barbara、Schmidt, E.、Remde, B.、Kipke, A.、Mueller, Ruth

  DOI：——

  日期：——