3-(4-nitrophenyl)-5-[methyl(phenylcarboxylate)]isoxazole | 1182713-84-3

• 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: 3-(4-nitrophenyl)-5-[methyl(phenylcarboxylate)]isoxazole
• 英文别名: 1-[3-(4-nitrophenyl)isoxazole-5-yl]methyl benzoate；3-(4-nitrophenyl)-5-(phenoxycarbonylmethyl)isoxazole；[3-(4-nitrophenyl)-1,2-oxazol-5-yl]methyl benzoate
• CAS: 1182713-84-3
• 化学式: C₁₇H₁₂N₂O₅
• 分子量: 324.293
• InChiKey: OPMGWNGMPMIAER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  98.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯酸炔丙酯 、 4-nitrobenzaldehyde oxime 在 sodium hypochlorite 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到3-(4-nitrophenyl)-5-[methyl(phenylcarboxylate)]isoxazole
  参考文献：
  名称：

  Synthesis and characterization of 2-alkyl -5-{4-[(3-nitrophenyl-5-isoxazolyl)methoxy]phenyl}-2H-tetrazoles

  摘要：

  Heteroaryl substituted analogs of antirhnoviral (A), was prepared by a convergent approach. 3-Nitrophenyl-5-bromooromethylisoxazoles 5a-b were synthesized by [3+2] cycloaddition of 3-(benzoyloxy)-propyne 2 to in situ generated arylnitrile oxides followed by deprotection of cycloadducts 3a-b and bromination of the resulting alcohols 4a-b. Coupling of 3-nitrophenyl-5-bromooromethylisoxazoles (5a-b) with 4-[5-(2-alkyl-2H-tetrazolyl)]phenols (6a-d) in N-methylpyrrolidinone under mild conditions afforded a new series of 2-alkyl-5-{4-[1-(3-nitrophenyl-5-isoxazoly)methyloxy]pheny}-2H-tetrazoles (7a-h) in high yields. The structures of the synthesized compounds were confirmed by their (1)H NMR, Mass spectral, and Elemental Analysis data.

  DOI：

  10.1007/bf03246058

文献信息

• The Regiospecific Synthesis of Some New 3,5-Disubstituted Isoxazoles
  作者：Ladan Edjlali

  DOI：10.1002/jccs.200800198

  日期：2008.12

  The compounds with isoxazole moiety have many pharmacological, biological and industrial applications, specifically their antiviral activity. In this research work, seven new compounds of3,5-disubstituted isoxazoles were synthesized. Propargyl alcohol (1) reacted with benzoyl chloride to give propargylphenylcarboxylate (2). Then, the aldehydes (3a-3g) were converted to the related oximes (4a-4g) and

  具有异恶唑部分的化合物具有许多药理学、生物学和工业应用，特别是它们的抗病毒活性。本研究工作合成了7种3,5-二取代异恶唑类新化合物。炔丙醇(1)与苯甲酰氯反应得到炔丙基苯基羧酸酯(2)。然后，醛（3a-3g）被NaOCl原位转化为相关的肟（4a-4g）和腈氧化物。化合物2与腈氧化物在[3+2]环加成反应中反应得到区域特异性异恶唑(5a-5g)。1 H NMR、13 C NMR、FT-IR和元素分析证实了合成化合物的结构。