pentane-2,3,4-trione 3-[(2-chloro-phenyl)-hydrazone] | 75304-21-1

• 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: pentane-2,3,4-trione 3-[(2-chloro-phenyl)-hydrazone]
• 英文别名: 3-(2-Chlor-benzolazo)-acetylaceton；3-[(2-Chlorophenyl)diazenyl]pentane-2,4-dione
• CAS: 75304-21-1
• 化学式: C₁₁H₁₁ClN₂O₂
• 分子量: 238.674
• InChiKey: YLBLVWNLJFMVGW-UHFFFAOYSA-N

物化性质

• 熔点：
  110 °C(Solv: ethanol (64-17-5))
• 沸点：
  310.3±42.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  58.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  pentane-2,3,4-trione 3-[(2-chloro-phenyl)-hydrazone] 在 盐酸羟胺 、 sodium acetate 、 potassium hydroxide 作用下， 以 水 为溶剂， 反应 6.5h， 生成 1-[3-methyl-2-(2-chlorophenyldiazenyl)-2H-aziren-2-yl]ethanone
  参考文献：
  名称：

  Synthesis and QSAR modeling 1-[3-methyl-2-(aryldiazenyl)-2H-aziren-2-yl]ethanones as potential antibacterial agents

  摘要：

  The present communication deals with the synthesis of a series of 1-[3-methyl-2-(aryldiazenyl)-2H-aziren-2-yl]ethanones. The compounds were synthesized in excellent yields (70-80 %), and the structures were established on the basis of consistent IR, H-1 NMR, and elemental analysis data. The purity has been ascertained by chromatographic resolution using hexane-ethyl acetate (6:4 v/v) as binary eluent. All the compounds have been tested for their antimicrobial activity against a representative panel of bacteria i.e., Bacillus subtilis, Escherichia coli, Pseudomonas diminuta, and Staphylococcus aureus using Chloramphenicol as reference drug. All the synthesized compounds were found to exhibit profound antimicrobial activity.

  DOI：

  10.1007/s00044-012-0242-4
• 作为产物：
  描述：

  邻氯苯胺 、 乙酰丙酮 在 盐酸 、 sodium nitrite 、 sodium acetate 作用下， 以 水 、 乙醇 为溶剂， 生成 pentane-2,3,4-trione 3-[(2-chloro-phenyl)-hydrazone]
  参考文献：
  名称：

  Synthesis and antimicrobial activity of pyrazolinones and pyrazoles having benzothiazole moiety

  摘要：

  A new class of 4-arylhydrazono-1-benzothiazolyl-3-methylpyrazolin-5-ones (3a-j) and 4-arylazo-1-benzothiazolyl-3,5-dimethylpyrazoles (4a-j) were designed as pharmacophore hybrids between pyrazolinone/pyrazole and benzothiazole moiety. The target molecules were efficiently synthesized by the cyclization of various oxobutyrates/pentane-2,4-dione derivatives with 6-chloro-2-hydrazinobenzothiazole in the presence of glacial acetic acid. The compounds were evaluated for their in vitro antimicrobial activity. Preliminary study of the structure-activity relationship revealed that electron-withdrawing groups in phenyl ring had a promising effect on the antimicrobial activity. Also, correlation study has been used to establish the relationships between the antibacterial activity and physicochemical parameter clogP.

  DOI：

  10.1007/s00044-011-9642-0

文献信息

• Synthesis and antimicrobial activity of pyrazolinones and pyrazoles having benzothiazole moiety
  作者：Mohd. Amir、Sadique A. Javed、Mohd. Zaheen Hassan

  DOI：10.1007/s00044-011-9642-0

  日期：2012.7

  A new class of 4-arylhydrazono-1-benzothiazolyl-3-methylpyrazolin-5-ones (3a-j) and 4-arylazo-1-benzothiazolyl-3,5-dimethylpyrazoles (4a-j) were designed as pharmacophore hybrids between pyrazolinone/pyrazole and benzothiazole moiety. The target molecules were efficiently synthesized by the cyclization of various oxobutyrates/pentane-2,4-dione derivatives with 6-chloro-2-hydrazinobenzothiazole in the presence of glacial acetic acid. The compounds were evaluated for their in vitro antimicrobial activity. Preliminary study of the structure-activity relationship revealed that electron-withdrawing groups in phenyl ring had a promising effect on the antimicrobial activity. Also, correlation study has been used to establish the relationships between the antibacterial activity and physicochemical parameter clogP.
• Pyridazine derivatives and related compounds. 23*. Synthesis of 3-substituted pyrazolo[3,4-c]pyridazines and their application as disperse dyes
  作者：A. Deeb、F. Yassin、N. Ouf、W. Shehta

  DOI：10.1007/s10593-010-0494-1

  日期：2010.6

  Acetylacetone and malononitrile were coupled with diazotized arylamines to give arylazoacetyl-acetones and arylazomalononitriles. When refluxed with 3-hydrazino-4,5-diphenyl-1H-pyrazolo-[3,4-c]pyridazine in the presence of ethanol/HCl, they yielded the corresponding 3-[4-(arylazo)-3,5-di-methylpyrazol-1-yl]- and 3-[3,5-diamino-4-(arylazo)pyrazol-1-yl]-4,5-diphenyl-1H-pyrazolo[3,4-c]pyri-dazine dyes. The dyes were applied to polyester and polyamide fabrics, and their spectral and fastness properties were measured.
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  作者：Garg,H.G.

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