3-(4-methoxyphenyl)-5-phenyl-4,5-dihydroisoxazol-5-ol | 146933-25-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-methoxyphenyl)-5-phenyl-4,5-dihydroisoxazol-5-ol
• 英文别名: 3-(4'-methoxy)phenyl-5-phenyl-2-isoxazolin-5-ol；3-(4-methoxy-phenyl)-5-phenyl-4,5-dihydro-isoxazol-5-ol；3-(4-methoxyphenyl)-5-phenyl-4H-1,2-oxazol-5-ol
• CAS: 146933-25-7
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: LTDXZWKJPGSCBU-UHFFFAOYSA-N

物化性质

• 熔点：
  130-132 °C
• 沸点：
  435.7±55.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  51
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyphenyl)-5-phenyl-4,5-dihydroisoxazol-5-ol 在 盐酸 作用下， 反应 1.0h， 生成 3-(4-甲氧基苯基)-5-苯基-1,2-恶唑
  参考文献：
  名称：

  Bandiera, T.; Gruenanger, P.; Albini, F. Marinone, Journal of Heterocyclic Chemistry, 1992, vol. 29, # 6, p. 1423 - 1428

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲氧基查耳酮 在 N-羟基-4-甲基苯磺酰胺 、 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以72%的产率得到3-(4-methoxyphenyl)-5-phenyl-4,5-dihydroisoxazol-5-ol
  参考文献：
  名称：

  Efficient and Regioselective Synthesis of 5-Hydroxy-2-isoxazolines: Versatile Synthons for Isoxazoles, β-Lactams, and γ-Amino Alcohols

  摘要：

  An efficient and highly regioselective protocol was developed for the preparation of 5-hydroxy-2-isoxazolines, which have been proved to be versatile synthons for isoxazles, beta-hydroxy oximes, and gamma-amino alcohols. beta-Lactams, commonly embedded in the skeletons of bioactive natural products, were also synthesized in two steps from beta-hydroxy oximes, providing a new strategy for the synthesis of this kind of compounds.

  DOI：

  10.1021/jo1000065

文献信息

• TEMPO‐Mediated Selective Synthesis of Isoxazolines, 5‐Hydroxy‐2‐isoxazolines, and Isoxazoles via Aliphatic <i>δ</i> ‐C(sp3)‐H Bond Oxidation of Oximes
  作者：Santanu Mondal、Sourabh Biswas、Krishna Gopal Ghosh、Devarajulu Sureshkumar

  DOI：10.1002/asia.202100572

  日期：2021.9

  Three heterocycles from one starting material: A divergent method for the synthesis of isoxazolines, isoxazoles, and 5-hydroxy-2-isoxazolines from oximes is developed using TEMPO as a radical initiator. Oxidants control the selectivity of the product formations.

  来自一种原料的三个杂环：使用 TEMPO 作为自由基引发剂开发了一种从肟合成异恶唑啉、异恶唑和 5-羟基-2-异恶唑啉的不同方法。氧化剂控制产物形成的选择性。
• Metal-free cascade synthesis of unsymmetrical 2-aminopyrimidines from imidazolate enaminones
  作者：Xue Cui、Jianting Ma、Tingting Zeng、Junyu Xu、Youbin Li、Xuesong Wang

  DOI：10.1039/d1ra04319f

  日期：——

  metal-free synthesis of unsymmetrical 2-aminopyrimidines from imidazolate enaminones has been developed. In this procedure, various structural 2-aminopyrimidines, as well as 4,5-dihydroisoxazol-5-ols and pyrazoles were synthesized in moderate to excellent yields. A plausible mechanism was also proposed for the cascade reaction. This method represents an effective strategy towards the synthesis of unsymmetrical

  已经开发了一种方便的从咪唑烯胺酮合成不对称 2-氨基嘧啶的无金属方法。在此过程中，各种结构的 2-氨基嘧啶以及 4,5-二氢异恶唑-5-醇和吡唑以中等至优异的产率合成。还提出了级联反应的合理机制。该方法代表了一种合成不对称 2-氨基嘧啶的有效策略。
• Joerlander, Chemische Berichte, 1916, vol. 49, p. 2792
  作者：Joerlander

  DOI：——

  日期：——
• Bandiera T., Gruenanger P., Albini F. Marinone, J. Heterocycl. Chem., 29 (1992) N 6, S 1423-1428
  作者：Bandiera T., Gruenanger P., Albini F. Marinone

  DOI：——

  日期：——
• Efficient and Regioselective Synthesis of 5-Hydroxy-2-isoxazolines: Versatile Synthons for Isoxazoles, β-Lactams, and γ-Amino Alcohols
  作者：Shibing Tang、Jinmei He、Yongquan Sun、Liuer He、Xuegong She

  DOI：10.1021/jo1000065

  日期：2010.3.19

  An efficient and highly regioselective protocol was developed for the preparation of 5-hydroxy-2-isoxazolines, which have been proved to be versatile synthons for isoxazles, beta-hydroxy oximes, and gamma-amino alcohols. beta-Lactams, commonly embedded in the skeletons of bioactive natural products, were also synthesized in two steps from beta-hydroxy oximes, providing a new strategy for the synthesis of this kind of compounds.