2-(2-phenylhydrazono)-2-bromo-1-(naphthalene-2-yl)ethanone | 140138-41-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2-phenylhydrazono)-2-bromo-1-(naphthalene-2-yl)ethanone
• 英文别名: 2-naphthalen-2-yl-2-oxo-N-phenylethanehydrazonoyl bromide
• CAS: 140138-41-6
• 化学式: C₁₈H₁₃BrN₂O
• 分子量: 353.218
• InChiKey: APEWEKJBEBOPCR-UHFFFAOYSA-N

物化性质

• 沸点：
  489.6±28.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.46
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(2-phenylhydrazono)-2-bromo-1-(naphthalene-2-yl)ethanone 在 sodium azide 、 四丁基碘化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以90%的产率得到2-(naphthalen-2-yl)-2-oxo-N-phenylacetohydrazonoyl azide
  参考文献：
  名称：

  Hassaneen, Hamdi M.; Elwan, Nehal M.; Abdelhadi, Hyam A., Organic Preparations and Procedures International, 1994, vol. 26, # 5, p. 588 - 593

  摘要：

  DOI：
• 作为产物：
  描述：

  N-亞硝乙醯胺苯 、 dimethyl (2-naphthoylmethyl)sulfonium bromide 以 乙醇 为溶剂， 反应 24.0h， 生成 2-(2-phenylhydrazono)-2-bromo-1-(naphthalene-2-yl)ethanone
  参考文献：
  名称：

  Hassaneen, Hamdi M.; Shawali, Ahmad S.; Elwan, Nehal M., Organic Preparations and Procedures International, 1992, vol. 24, # 2, p. 171 - 175

  摘要：

  DOI：

文献信息

• Synthesis of Novel Triazoles, Tetrazine, Thiadiazoles and Their Biological Activities
  作者：Mohammed Al-Omair、Abdelwahed Sayed、Magdy Youssef

  DOI：10.3390/molecules20022591

  日期：——

  An expedient synthesis of novel triazoles, tetrazine and thiadiazoles, using conveniently accessible and commercially available starting materials has been achieved. The synthesized compounds were characterized by spectroscopic and elemental analyses, and screened for their antibacterial activities against four different strains, namely E. coli, P. aeruginosa, S. aureus and B. megaterium. In particular, the compounds 5, 24 and 26h exhibited excellent antibacterial activities compared to the reference antibiotic. To get further insight about their behavior, these compounds were tested for their antioxidant activities via SOD-like activity, DPPH free radical scavenging activity, ABST and NO, which showed promising results. Furthermore, these compounds effectively promoted the cleavage of genomic DNA as well, in the absence of any external additives.

  利用方便易得的市售起始材料，实现了新型三唑、四氮杂嗪和噻二唑的快速合成。通过光谱和元素分析对合成的化合物进行了表征，并筛选了它们对四种不同菌株（即大肠杆菌、铜绿假单胞菌、金黄色葡萄球菌和巨大芽孢杆菌）的抗菌活性。与参考抗生素相比，化合物 5、24 和 26h 尤其表现出卓越的抗菌活性。为了进一步了解这些化合物的行为，研究人员通过 SOD 样活性、DPPH 自由基清除活性、ABST 和 NO 测试了它们的抗氧化活性。此外，在没有任何外部添加剂的情况下，这些化合物还能有效促进基因组 DNA 的裂解。
• Utility of 2-Acetyl Benzofuran for the Synthesis of New Heterocycles as Potential Anticancer Agents
  作者：Anhar Abdel-Aziem

  DOI：10.1002/jhet.2906

  日期：2017.11

  series of benzofuran derivatives containing thiazole, thiadiazine, and pyridotriazolopyrimidine were synthesized starting from 1‐(benzofuran‐2‐yl)‐3‐(1H–indol‐3‐yl)prop‐2‐en‐1‐one. Also, triazolopyrimidine derivatives were prepared from the reaction of 2‐acetylbenzofuran and pyrazole‐4‐carbaldehyde with 2‐thiobarbutyric acid and reaction of the product with hydrazonoyl halides. The structures of the

  从1-（苯并呋喃-2-基）-3-（1 H开始合成了一系列包含噻唑，噻二嗪和吡啶三唑并嘧啶的苯并呋喃衍生物–indol-3-yl）prop-2-en-1-one。同样，三唑并嘧啶衍生物是由2-乙酰基苯并呋喃和吡唑-4-甲醛与2-硫代巴丁酸反应，以及产物与酰卤反应制得的。根据元素分析，光谱数据和可能的替代合成路线，阐明了新合成化合物的结构。美国国家癌症研究所已通过两步验证了针对60种不同的代表白血病，黑素瘤和肺癌，结肠癌，脑癌，卵巢癌，乳腺癌，前列腺癌和肾癌的人类肿瘤细胞系的抗癌活性。结果显示吡唑啉-1-硫代碳酰肼4b，三唑并嘧啶20d和嘧啶硫酮25 具有针对大多数细胞系的有希望的抗肿瘤活性。
• A Facile and Convenient Method for the Synthesis of Bis-Hydrazonoyl Halides and Bis-(1,3,4-Thiadiazol-3-ylphenoxy)Ethers
  作者：Ashraf A. Abbas、Nora M. Rateb

  DOI：10.1080/104265090517226

  日期：2005.2

  Abstract New bis(thiadiazole) derivatives 7a–m were prepared in good yields by the reaction of the appropriate hydrazonoyl halides 4a–e with the bis-Schiff bases 9a–c. Similarly, the bis(thiadiazole) derivatives 17a–g were prepared by the reaction of the novel bis-hydrazonoyl halides 13a–d with schiff bases 3a–d.

  摘要 通过适当的腙酰卤 4a-e 与双席夫碱 9a-c 反应，以良好的收率制备了新的双（噻二唑）衍生物 7a-m。同样，双（噻二唑）衍生物 17a-g 是通过新型双腙酰卤 13a-d 与席夫碱 3a-d 反应制备的。
• Synthesis, Acidity Constants and Tautomeric Structure of 7-Arylhydrazono[1,2,4]Triazolo[3,4-b][1,3,4]thiadiazines in Ground and Excited States
  作者：Ahmad S. Shawali、Ibrahim F. Zeid、Mahmoud H. Abdelkader、Alsayed A. Elsherbini、Farag M. A. Altalbawy

  DOI：10.1002/jccs.200100012

  日期：2001.2

  7-Arylhydrazono[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines 4 were synthesized from the reactions of 4-amino-5-phenyl-4H-[1,2,4]triazole-3-thiol 2 and 2-(2-naphthyl)-2-oxoethanehydrazonoyl bromides 1 and their acid dissociation constants pK and pK*, in the ground and excited states, respectively, were determined. Both pK and pK* constants were correlated by Hammett equation. The pK and the spectral data

  7-芳基肼[1,2,4]三唑并[3,4-b][1,3,4]噻二嗪4由4-氨基-5-苯基-4H-[1,2,4]反应合成分别测定了三唑-3-硫醇 2 和 2-(2-萘基)-2-氧代乙烷腙酰溴 1 及其酸解离常数 pK 和 pK*，分别处于基态和激发态。pK 和 pK* 常数都通过 Hammett 方程相关。提供的 pK 和光谱数据表明标题化合物主要以腙互变异构形式存在。
• Reactions with Hydrazonoyl Halides 34¹: Synthesis of Some New 2,3-Dihydro-1,3,4-thiadiazoles
  作者：Omer S. Abu-Team、Nora M. Rateb、Abdou O. Abdelhamid

  DOI：10.1080/714040950

  日期：2003.11.1

  Hydrazonoyl halides 4a–h have been caused to react with each of alkyl carbodithioates (3, 13–17)a,b in the presence of triethylamine to give 2,3-dihydro-1,3,4-thiadiazoles in good yields. Structures of the new compounds were elucidated on the basis of elemental analyses, spectral data, and alternative methods of synthesis whenever possible.

  在三乙胺的存在下，腙酰卤 4a-h 与每种碳二硫代烷基酯 (3, 13-17)a,b 反应，以良好的收率得到 2,3-二氢-1,3,4-噻二唑。新化合物的结构是在元素分析、光谱数据和其他可能的合成方法的基础上阐明的。