3-(4-bromophenyl)-5-p-tolyl-4,5-dihydroisoxazole | 1147841-44-8

• 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-bromophenyl)-5-p-tolyl-4,5-dihydroisoxazole
• 英文别名: 3-(4-bromophenyl)-5-(4-(methyl)phenyl)-4,5-dihydroisoxazole；3-(4-Bromophenyl)-5-(4-methylphenyl)-4,5-dihydro-1,2-oxazole
• CAS: 1147841-44-8
• 化学式: C₁₆H₁₄BrNO
• 分子量: 316.197
• InChiKey: WKQVRCPIXWLVPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-bromophenyl)-5-p-tolyl-4,5-dihydroisoxazole 在 manganese(IV) oxide 作用下， 以 苯 为溶剂， 反应 10.0h， 以67%的产率得到3-(4-bromophenyl)-5-(4-(methyl)phenyl)isoxazole
  参考文献：
  名称：

  Expeditious preparation of isoxazoles from Δ2-isoxazolines as advanced intermediates for functional materials

  摘要：

  A collection of isoxazoles derivatives has been efficiently synthesized in three steps. The oximation reaction of aldehydes followed by nitrile oxide [3+2] 1,3-dipolar cycloaddition and MnO2-oxidation reaction furnished the title compounds which were purified by simple filtration on celite (R). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.09.122
• 作为产物：
  描述：

  对溴苯甲醛 在 吡啶 、 N-氯代丁二酰亚胺 、 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 反应 5.0h， 生成 3-(4-bromophenyl)-5-p-tolyl-4,5-dihydroisoxazole
  参考文献：
  名称：

  Expeditious preparation of isoxazoles from Δ2-isoxazolines as advanced intermediates for functional materials

  摘要：

  A collection of isoxazoles derivatives has been efficiently synthesized in three steps. The oximation reaction of aldehydes followed by nitrile oxide [3+2] 1,3-dipolar cycloaddition and MnO2-oxidation reaction furnished the title compounds which were purified by simple filtration on celite (R). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.09.122

文献信息

• [2 + 2 + 1] Heteroannulation of Alkenes with Enynyl Benziodoxolones and Silver Nitrite Involving C≡C bond Oxidative Cleavage: Entry to 3-Aryl-Δ²-isoxazolines
  作者：Cheng-Yong Wang、Fan Teng、Yang Li、Jin-Heng Li

  DOI：10.1021/acs.orglett.0c01285

  日期：2020.6.5

  A copper-catalyzed [2 + 2 + 1] heteroannulation of alkenes with enynyl benziodoxolones and AgNO2 involving oxidative cleavage of the C≡C bond promoted by cooperative Zn(OTf)2, KOAc, and 4 Å MS for producing 3-aryl Δ2-isoxazolines is reported. Mechanistic studies indicate that AgNO2 serves as the N/O two-atom unit source, enabling the formation of three bonds through NO2 addition across the C≡C bond

  铜催化的[2 + 2 + 1]烯烃与烯丙基苯并恶唑烷酮和AgNO 2的杂环化反应，涉及由Zn（OTf）2，KOAc和4ÅMS协同促进的C≡C键的氧化裂解，从而产生3-芳基Δ报告了2-异恶唑啉。机理研究表明，AgNO 2充当N / O两原子单元源，可通过在C≡C键，NO转移，C≡C键裂解和环合级联反应中添加NO 2形成三个键。