3-Bromo-4'-chlorochalcone | 77153-27-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-Bromo-4'-chlorochalcone
• 英文别名: 3-(3-Bromophenyl)-1-(4-chlorophenyl)prop-2-en-1-one
• CAS: 77153-27-6
• 化学式: C₁₅H₁₀BrClO
• 分子量: 321.601
• InChiKey: CLCKUHZBRBOVTR-UHFFFAOYSA-N

物化性质

• 熔点：
  185 °C
• 沸点：
  435.4±45.0 °C(Predicted)
• 密度：
  1.475±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-Bromo-4'-chlorochalcone 在 ammonium acetate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 10.0h， 生成 trichloro[4-(3-bromophenyl)-2-(4-chlorophenyl)-6-(thiophen-2-yl)pyridine](triphenylphosphine)ruthenium(III)
  参考文献：
  名称：

  Monitoring the DNA by ruthenium complexes of heterocyclic N,S-donor ligands and evaluation of biological activities

  摘要：

  Neutral N,S-donor bidentate ligands have been synthesized and characterized by NMR and IR spectroscopic techniques. The ligands have been used to synthesized ruthenium(II) complexes ([Ru(L-1-L-6)PPh3)(2)Cl-2]) and ruthenium(III) complexes ([Ru(L-1-L-6)PPh3)Cl-3]). Synthesized complexes have been characterized using elemental analysis, UV-Vis spectroscopy, magnetic measurements, LC-MS, and IR spectroscopy. Broth dilution technique was used to investigate antibacterial activity against two Gram-positive and three Gram-negative microorganisms and results show that all complexes are more potent than the respective ligands. UV-Vis absorption titration and viscosity measurements have been carried out to investigate the binding mode and binding strength of complexes with herring sperm DNA. The quantitative binding strength (K (b)) of the complexes was found in the range of 0.521 x 10(5)-2.94 x 10(5) M-1 and indicate intercalative mode of binding. Gel electrophoresis study was carried out to study the cleavage of pUC19 supercoiled DNA. DNA nuclease activity data for the complexes are found higher than respective ligands and metal salt. Brine shrimp bioassay was carried out to perform cytotoxicity study. IC50 values of the complexes were found in the range of 5.69 +/- 1.06-14.62 +/- 0.87 mu g cm(-3).

  DOI：

  10.1007/s00706-016-1708-8
• 作为产物：
  描述：

  间溴苯甲醛 、 对氯苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.5h， 以85%的产率得到3-Bromo-4'-chlorochalcone
  参考文献：
  名称：

  Kinetic study of the homolytic brominolysis of 1,2-diarylcyclopropanes

  摘要：

  DOI：

  10.1021/jo00325a014

文献信息

• Asymmetric epoxidation of α,β-unsaturated ketones catalyzed by rare-earth metal amides RE[N(SiMe₃)₂]₃with chiral TADDOL ligands
  作者：Haiwen Shan、Chengrong Lu、Bei Zhao、Yingming Yao

  DOI：10.1039/d0nj05228k

  日期：——

  The catalytic asymmetric epoxidation of α,β-unsaturated ketones by tert-butylhydroperoxide (TBHP) has been well established using rare-earth metal amides RE[N(SiMe3)2]3 (RE = La(1), Nd(2), Sm(3), Y(4), Yb(5)) with chiral TADDOL ligands. It was found that the combination of Yb[N(SiMe3)2]3 and chiral TADDOL ligand H2L2 ((4S,5S)-2,2-dimethyl-α,α,α′,α′-tetra-3,5-bis(trifluormethylphenyl)-1,3-dioxolane-4

  α的催化不对称环氧化，通过β不饱和酮叔-butylhydroperoxide（TBHP）已经很好地使用稀土类金属酰胺建立RE [N（森达3）2 ] 3（RE = La（上1），钕（2） ，Sm（3），Y（4），Yb（5））和手性TADDOL配体。发现Yb [N（SiMe 3）2 ] 3和手性TADDOL配体H 2 L 2（（4 S，5 S）摩尔比为1：1的）-2,2-二甲基-α，α，α'，α'-tetra-3,5-双（三氟甲基苯基）-1,3-二氧戊环-4,5-二甲醇）最佳选择，使用DBU作为添加剂，可以以优异的收率（89–99％）和良好至高的对映选择性（57–94％ee）提供所需的环氧化物。各种底物被证明具有官能团耐受性。此外，还进行了克级实验和衍生化实验。
• DABCO-catalyzed three-component reaction for the synthesis of naphtho[2,3-b]thiophene-4,9-diones
  作者：Yun Liu、Wenhui Ge、Junwen Han、Youquan Zhu、Yanhui Shi、Hui Wu

  DOI：10.1016/j.tetlet.2017.05.081

  日期：2017.7

  9-diones has been developed via DABCO-catalyzed three-component reaction of 1,4-naphthoquinone derivatives, α,β-unsaturated ketones and hydrated sodium sulfide. The reaction is initiated by sequential Michael additions of sodium sulfide to α,β-unsaturated ketone and of generated anion to 1,4-naphthoquinone derivative, followed by intramolecular oxidative cyclization and aromatization. Various functional groups

  通过DABCO催化的1,4-萘醌衍生物，α，β-不饱和酮和水合硫化钠的三组分反应，已经开发了萘并[2,3 - b ]噻吩-4,9-二酮的有效合成方法。通过依次向α，β-不饱和酮中添加硫化钠，并向1，4-萘醌衍生物中生成阴离子，依次进行迈克尔的加成反应，然后进行分子内氧化环化和芳构化，来引发反应。在反应条件下，α，β-不饱和酮中的各种官能团得以存活，并且以高收率产生了萘并[2,3 - b ]噻吩-4,9-二酮。
• Michael-Michael Aldol Reaction of Chalcones with Cyanoacetylurea and Cyanoacetylpiperidine
  作者：Hani D. Tabba、Nidal M. Yousef、Mohammad M. Al-Arab

  DOI：10.1135/cccc19950594

  日期：——

  Several highly substituted cyclohexane derivatives were synthesized by the one-pot condensation of chalcones and cyanoacetylurea (2 : 1) using sodium alkoxide in anhydrous alcohol at room temperature. The structure of the reaction products was established by infrared, ¹H and ¹³C NMR spectroscopy as well as by their elemental analysis. Single crystal X-ray crystallography shows the presence of the cyclohexane moiety.

  通过使用钠烷氧基在无水醇中室温下，将香豆素和氰乙酰脲（2：1）一锅法缩合合成了几种高度取代的环己烷衍生物。通过红外、¹H和¹³C核磁共振光谱以及元素分析，确定了反应产物的结构。单晶X射线衍射显示了环己烷基团的存在。
• A direct green route towards the synthesis of 2-aroyl-3,5-diarylthiophenes from 1,5-diketones
  作者：Rengasamy Chithiravel、Kandasamy Rajaguru、Shanmugam Muthusubramanian、Nattamai Bhuvanesh

  DOI：10.1039/c5ra17829k

  日期：——

  The synthesis of 2-aroyl-3,5-diarylthiophenes has been achieved from various 1,5-diketones with elemental sulphur and morpholine under microwave irradiation following a greener protocol.

  已经通过微波辐射在一种更环保的方法下，利用各种1,5-二酮与元素硫和吗啡啶合成了2-芳酰基-3,5-二芳基噻吩。
• A facile, water mediated, microwave-assisted synthesis of 4,6-diaryl-2,3,3a,4-tetrahydro-1H-pyrido[3,2,1-jk]carbazoles by a domino Fischer indole reaction–intramolecular cyclization sequence
  作者：Selvam Chitra、Nidhin Paul、Shanmugam Muthusubramanian、Paramasivam Manisankar

  DOI：10.1039/c1gc15483d

  日期：——

  benign, facile and efficient synthesis of a series of 4,6-diaryl-2,3,3a,4-tetrahydro-1H-pyrido[3,2,1-jk]carbazoles was achieved in water with good yield by the reaction of diastereomerically pure 2-(3-oxo-1,3-diarylpropyl)-1-cyclohexanones with phenylhydrazine hydrochloride under microwave irradiation. The transformation presumably proceeds via a domino Fischer indole reaction–intramolecular cyclisation

  一系列的4,6-二芳基-2,3,3a，4-四氢-1 H-吡啶并[3,2,1- jk ]咔唑的环境友好，简便而有效的合成得以实现。水 非对映体纯的2-（3-氧代-1,3-二芳基丙基）-1-环己酮与 盐酸苯肼在微波照射下。这种转变大概是通过多米诺菲舍尔（Domino Fischer）进行的吲哚 反应-分子内 环化 顺序。