4-bromo-2-(((5-chloro-2-hydroxyphenyl)imino)methyl)phenol | 1761-38-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-bromo-2-(((5-chloro-2-hydroxyphenyl)imino)methyl)phenol
• 英文别名: 4-Bromo-2-(((5-chloro-2-hydroxyphenyl) imino)methyl)phenol；2-[(5-bromo-2-hydroxyphenyl)methylideneamino]-4-chlorophenol
• CAS: 1761-38-2
• 化学式: C₁₃H₉BrClNO₂
• 分子量: 326.577
• InChiKey: GULJBNBZIVDAHF-UHFFFAOYSA-N

物化性质

• 熔点：
  200.0-200.5 °C
• 沸点：
  506.1±50.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,10-菲罗啉 、 copper(II) acetate monohydrate 、 4-bromo-2-(((5-chloro-2-hydroxyphenyl)imino)methyl)phenol 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 3.5h， 以78%的产率得到(1,10-phenanthroline)[4-bromo-2-((5-chloro-2-hydroxyphenylimino)methyl)phenol]copper(II) hydrate
  参考文献：
  名称：

  Synthesis, structural, and thermal analyses of copper(II) and oxido-vanadium(IV) complexes of 4-bromo-2-(((5-chloro-2-hydroxyphenyl)imino)methyl)phenol

  摘要：

  Reaction of 4-bromo-2-(((5-chloro-2-hydroxyphenyl)imino)methyl)phenol (H2L) with Cu(OAc)(2)center dot 4H(2)O or VOSO4 center dot 3H(2)O and 2,2 '-bipyridine (bipy) or 1,10-phenanthroline (phen) in a 1:1:1mol ratio led to [CuL(phen)] and [VOL(bipy)] which have distorted square pyramidal and octahedral geometries, respectively. The compounds were characterized by elemental analyses, FT-IR, UV-Vis, TGA, and X-ray diffraction. Their thermolyses have three stages: phen or bipy removal, separation of H2L minus chloride and bromide of H2L, and complete thermal decomposition to the metal oxide.

  DOI：

  10.1080/00958972.2013.815343
• 作为产物：
  描述：

  5-溴水杨醛 、 4-氯-2-氨基苯酚 以 乙醇 为溶剂， 反应 3.0h， 以90%的产率得到4-bromo-2-(((5-chloro-2-hydroxyphenyl)imino)methyl)phenol
  参考文献：
  名称：

  4-氯-2-氨基苯酚和各种水杨醛衍生物衍生的一些席夫碱的光谱表征和抑菌活性

  摘要：

  使用适当的合成路线合成了一系列N-（5-氯-2-羟基苯基）-（3/4 / 5-取代）-水杨醛亚胺（I - XI）。通过FT-IR，UV-Visible，ESI-MS，1 H和13 C NMR光谱技术和分析方法对它们的结构进行了表征。N-（5-氯-2-羟基苯基）-5-溴水杨基醛亚胺（V）的晶体结构在室温下通过X射线衍射测定。研究了熔点与化合物结构之间的关系。评估了该化合物对金黄色葡萄球菌，表皮葡萄球菌，大肠杆菌，肺炎克雷伯菌，铜绿假单胞菌，奇异变形杆菌。据报道，白色念珠菌具有抗真菌活性。席夫碱表现出了相当的抗菌活性对金黄色葡萄球菌，表皮葡萄球菌和Ç。白色的。N-（5-氯-2-羟基苯基）-3-羟基水杨基亚胺（II）具有最广泛和最高的抗菌活性。

  DOI：

  10.1002/cjoc.201180473

文献信息

• Two ligand oxidio-vanadium(IV) complexes as novel efficient catalysts in multicomponent reactions for synthesis of tetrahydrobenzopyran derivatives
  作者：M. Abaszadeh、M. Seifi、S. Y. Ebrahimipour

  DOI：10.4314/bcse.v30i2.9

  日期：——

  Two ligand oxido-vanadium(IV) complexes, [VO(L)(bipy)] (Ι) and [VO(L)(phen)] (ΙΙ); [H2L:    4-bromo-2-(((5-chloro-2-hydroxyphenyl)imino)methyl)phenol, bipy: 2,2’-bipyridine and phen: 1,10- phenanthroline], have been synthesized and characterized by elemental analysis, FT-IR, UV-Vis and conductivity measurements. These complexes, as new catalysts, were also used to synthesize the tetrahydrobenzopyran derivatives by three-component reaction of cyclic β-dicarbonyl compounds, malononitrile and aromatic aldehydes, in EtOH, at reflux. Inexpensiveness, stability and the potential of being easily obtained can be noted as preponderance of these catalysts. Furthermore, high conversions, short reaction times and cleaner reaction profiles, are some of the advantages of this method. These catalysts can be recovered and reused several times without loss of activity.

  已合成并表征了两个双配体氧化钒(IV)配合物[VO(L)(bipy)] (I)和[VO(L)(phen)] (II)；[H2L为4-溴-2-(((5-氯-2-羟基苯基)亚氨基)甲基)苯酚，bipy为2,2'-联吡啶，phen为1,10-菲罗啉]。通过元素分析、傅里叶红外光谱、紫外-可见光谱和电导率测量对这些配合物进行了表征。 这些配合物作为新型催化剂，被用于在乙醇回流条件下，通过环状β-二羰基化合物、丙二腈和芳香醛的三组分反应合成四氢苯并吡喃衍生物。这些催化剂的优势在于价格低廉、稳定性好且易于获得。此外，该方法的优点包括高转化率、反应时间短和更清洁的反应过程。这些催化剂可以回收并重复使用多次而不会失去活性。
• Vanadium complex: an appropriate candidate for killing hepatocellular carcinoma cancerous cells
  作者：Hamid Bakhshi Aliabad、Soudeh Khanamani Falahati-pour、Hadis Ahmadirad、Maryam Mohamadi、Mohammad Reza Hajizadeh、Mehdi Mahmoodi

  DOI：10.1007/s10534-018-0139-x

  日期：2018.12

  Hepatocellular carcinoma (HCC) is a prevalent human malignancy which its drug resistance is increasing world-wide. This project was designed to assess the anti-cancer effects of 4-bromo-2-(((5-chloro-2-hydroxyphenyl) imino) methyl) phenol ([IV(L)] complex) on the HepG2 cell line and also L929 cells, as normal cells. HepG2 and L929 cells were cultured in RPMI culture medium and the survival rates of the cells were determined after 24 and 48h using MTT assay to find IC50 concentration of vanadium m, [IV(L)] complex. The early apoptosis and necrosis/late apoptosis were determined by means of annexin V/PI apoptosis detection kit. The results revealed that vanadium m, [IV(L)] complex induce early apoptosis higher in HepG2 cell line than L929 cells. The rates of necrosis/late apoptosis were also induced in HepG2 cells more than L929 cells. Based on the results, vanadium m, [IV(L)] complex might be considered as a safe new drug for treatment of HCC with low side effects on control liver cells.