(E)-1-([1,1'-biphenyl]-4-yl)-3-(4-bromothiophen-2-yl)prop-2-en-1-one | 1002461-30-4

• 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: (E)-1-([1,1'-biphenyl]-4-yl)-3-(4-bromothiophen-2-yl)prop-2-en-1-one
• 英文别名: (2E)-1-(biphenyl-4-yl)-3-(4-bromothiophen-2-yl)prop-2-en-1-one；(2E)-1-(biphenyl-4-yl)-3-(4-bromo-2-thienyl)prop-2-en-1-one；(E)-3-(4-bromothiophen-2-yl)-1-(4-phenylphenyl)prop-2-en-1-one
• CAS: 1002461-30-4
• 化学式: C₁₉H₁₃BrOS
• 分子量: 369.282
• InChiKey: NDOBPNNFQPORNS-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-溴-2-噻吩甲醛 、 联苯单乙酮 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 (E)-1-([1,1'-biphenyl]-4-yl)-3-(4-bromothiophen-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  Experimental and theoretical spectroscopic and structural analyses of a new chalcone single crystal derived from 4-bromo-2-thiophenecarboxaldehyde

  摘要：

  A new chalcone compound, (E)-1-([1,1 '-Biphenyl]-4-yl)-3-(4-bromothi ophen-2-yl)prop-2-en-1-one (BBTP), crystallizes in the monoclinic space group P2(1)/c and its structure has been characterized by Fourier transform infrared (FTIR), nuclear magnetic resonance (NMR), and ultraviolet and visible (UV-Vis) absorption spectroscopy. The structural and spectroscopic analyses of the chalcone were calculated using DFT/B3LYP method. Molecular structure, crystal structure arrangement, and intermolecular hydrogen bond interactions were determined by single crystal X-ray diffraction method. In the crystal packing, intermolecular C-H center dot center dot center dot O hydrogen bonds and C-H center dot center dot center dot pi interaction formed infinite two-dimensional sheets, thus strengthening the crystal structure. Hirshfeld surface analysis, HOMO-LUMO, and molecular electrostatic potential results are also reported.

  DOI：

  10.1080/15421406.2017.1328222

文献信息

• [EN] METHODS FOR PHOSPHINE OXIDE REDUCTION IN CATALYTIC WITTIG REACTIONS<br/>[FR] PROCÉDÉS POUR LA RÉDUCTION D'UN OXYDE DE PHOSPHINE DANS DES RÉACTIONS DE WITTIG CATALYTIQUES
  申请人：UNIV DUBLIN CITY

  公开号：WO2014140353A1

  公开（公告）日：2014-09-18

  A method for increasing the rate of phosphine oxide reduction, preferably during a Wittig reaction comprising use of an acid additive is provided. A room temperature catalytic Wittig reaction (CWR) the rate of reduction of the phosphine oxide is increased due to the addition of the acid additive is described. Furthermore, the extension of the CWR to semi-stabilized and non-stabilized ylides has been accomplished by utilization of a masked base and/or ylide-tuning.

  提供了一种增加磷氧化物还原速率的方法，尤其是在Wittig反应中，该方法包括使用酸性添加剂。描述了一种室温催化的Wittig反应（CWR），由于添加了酸性添加剂，磷氧化物还原的速率得到了提高。此外，通过利用掩蔽碱和/或调节基团，CWR已成功扩展到半稳定和不稳定的亚磷酰化物。
• Breaking the Ring through a Room Temperature Catalytic Wittig Reaction
  作者：Christopher J. O'Brien、Florie Lavigne、Emma E. Coyle、Andrew J. Holohan、Bryan J. Doonan

  DOI：10.1002/chem.201300546

  日期：2013.5.3

  One ring no longer rules them all: Employment of 2.5–10 mol % of 4‐nitrobenzoic acid with phenylsilane led to the development of a room temperature catalytic Wittig reaction (see scheme). Moreover, these enhanced reduction conditions also facilitated the use of acyclic phosphine oxides as catalysts for the first time. A series of alkenes were produced in moderate to high yield and selectivity.

  一个环不再完全统治一切：用2.5-10 mol％的4-硝基苯甲酸与苯基硅烷一起使用导致了室温催化Wittig反应的发展（参见方案）。此外，这些增强的还原条件还促进了首次将无环氧化膦用作催化剂。以中等至高收率和选择性生产了一系列烯烃。
• METHODS FOR PHOSPHINE OXIDE REDUCTION IN CATALYTIC WITTIG REACTIONS
  申请人：DUBLIN CITY UNIVERSITY

  公开号：US20160016860A1

  公开（公告）日：2016-01-21

  A method for increasing the rate of phosphine oxide reduction, preferably during a Wittig reaction comprising use of an acid additive is provided. A room temperature catalytic Wittig reaction (CWR) the rate of reduction of the phosphine oxide is increased due to the addition of the acid additive is described. Furthermore, the extension of the CWR to semi-stabilized and non-stabilized ylides has been accomplished by utilization of a masked base and/or ylide-tuning.

  提供了一种增加膦氧化物还原速率的方法，特别是在威特希格反应中使用酸添加剂。描述了室温催化威特希格反应（CWR），由于添加酸添加剂，膦氧化物的还原速率增加。此外，通过利用掩蔽碱和/或易化物调节，已经实现了CWR的扩展到半稳定和非稳定的易化物。
• Experimental and theoretical spectroscopic and structural analyses of a new chalcone single crystal derived from 4-bromo-2-thiophenecarboxaldehyde
  作者：Dian Alwani Zainuri、Suhana Arshad、Nuridayanti Che Khalib、Ibrahim Abdul Razak

  DOI：10.1080/15421406.2017.1328222

  日期：2017.6.13

  A new chalcone compound, (E)-1-([1,1 '-Biphenyl]-4-yl)-3-(4-bromothi ophen-2-yl)prop-2-en-1-one (BBTP), crystallizes in the monoclinic space group P2(1)/c and its structure has been characterized by Fourier transform infrared (FTIR), nuclear magnetic resonance (NMR), and ultraviolet and visible (UV-Vis) absorption spectroscopy. The structural and spectroscopic analyses of the chalcone were calculated using DFT/B3LYP method. Molecular structure, crystal structure arrangement, and intermolecular hydrogen bond interactions were determined by single crystal X-ray diffraction method. In the crystal packing, intermolecular C-H center dot center dot center dot O hydrogen bonds and C-H center dot center dot center dot pi interaction formed infinite two-dimensional sheets, thus strengthening the crystal structure. Hirshfeld surface analysis, HOMO-LUMO, and molecular electrostatic potential results are also reported.