3-(4-methoxyphenyl)-5-propylisoxazole

• 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-propylisoxazole
• 英文别名: 3-(4-Methoxyphenyl)-5-propyl-1,2-oxazole；3-(4-methoxyphenyl)-5-propyl-1,2-oxazole
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: IRIOHHFMELHJIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyphenyl)-5-propylisoxazole 在 三氟二甲基硫醚络合物 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以75%的产率得到3-(4-hydroxyphenyl)-5-propylisoxazole
  参考文献：
  名称：

  Microwave-assisted synthesis of 3,5-disubstituted isoxazoles and evaluation of their anti-ageing activity

  摘要：

  One-pot uncatalysed microwave-assisted 1,3-dipolar cycloaddition reactions between in situ generated nitrile oxides and alkynes bearing protected antioxidant substituents, were regioselectively afforded 3,5-disubstituted isoxazoles. The yields were moderate, based on the starting aldehydes, while the reaction times were in general shorter than those reported in the literature. The cytoprotective and anti-ageing effect of the final deprotected compounds was evaluated in vitro, on cellular survival following oxidative challenge and in vivo, on organismal longevity using the nematode Caenorhabditis elegans. The activity of the isoxazole analogues depends on the nature and the number of the antioxidant substituents. Analogue 17 bearing a phenolic group and a 6-OH-chroman group is a promising anti-ageing agent, since it increased survival of human primary fibroblasts following treatment with H2O2 and extended C. elegans lifespan.

  DOI：

  10.1016/j.ejmech.2014.06.046
• 作为产物：
  描述：

  1-(4-Methoxyphenyl)hex-2-yn-1-ol 在 四丁基氟化铵 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.75h， 生成 3-(4-methoxyphenyl)-5-propylisoxazole
  参考文献：
  名称：

  丙炔醇通过丙炔N-羟胺一锅法合成3,5-二取代异恶唑

  摘要：

  已经描述了一种从炔丙醇合成 3,5-二取代异恶唑的有效方法。该策略涉及一锅 p-TSA 催化的受保护羟胺的 N-炔丙基化，然后是 TBAF 介导的 5-endo-dig 环化。该方法已成功用于合成各种3,5-二取代异恶唑。

  DOI：

  10.1002/ejoc.201200628

文献信息

• Synergistic effect of dual-frequency ultrasound irradiation in the one-pot synthesis of 3,5-disubstituted isoxazoles
  作者：Maria Koufaki、Theano Fotopoulou、Georgios A. Heropoulos

  DOI：10.1016/j.ultsonch.2013.05.012

  日期：2014.1

  Herein is reported a one-pot three-step process for the regioselective synthesis of 3,5-disubstituted isoxazoles based on copper(I)-catalyzed cycloaddition reaction between in situ generated nitrile oxides (from the corresponding aldehydes) and alkynes, using ultrasound irradiation, avoiding toxic reagents and solvents and isolation/purification of intermediates. The combined use of 40 kHz ultrasonic

  本文报道了一种基于一锅法的三步法，该方法是利用铜（I）在原位生成的腈氧化物（来自相应的醛）与炔烃之间进行铜（I）催化的环加成反应，通过超声辐射进行区域选择性合成3,5-二取代的异恶唑，避免使用有毒的试剂和溶剂以及中间体的分离/纯化。在铜车削的情况下，结合使用40 kHz超声波浴和20 kHz探头，可将反应时间缩短至1h，并且仅进行一个最终纯化步骤即可提高产率，这清楚表明存在双频协同效应。另外，在无金属的条件下，1，3-偶极环加成是区域选择性的，给出低至中等的产率。
• One-Pot Synthesis of 3,5-Disubstituted Isoxazoles from Propargylic Alcohols through Propargylic<i>N</i>-Hydroxylamines
  作者：Chada Raji Reddy、Jonnalagadda Vijaykumar、Enukonda Jithender、Gangireddy Pavan Kumar Reddy、René Grée

  DOI：10.1002/ejoc.201200628

  日期：2012.10

  An efficient approach has been described for the synthesis of 3,5-disubstituted isoxazoles from propargylic alcohols. The strategy involves a one-pot p-TSA-catalyzed N-propargylation of protected hydroxylamines followed by a TBAF-mediated detosylative 5-endo-dig cyclization. The method was successfully used for the synthesis of various 3,5-disubstituted isoxazoles.

  已经描述了一种从炔丙醇合成 3,5-二取代异恶唑的有效方法。该策略涉及一锅 p-TSA 催化的受保护羟胺的 N-炔丙基化，然后是 TBAF 介导的 5-endo-dig 环化。该方法已成功用于合成各种3,5-二取代异恶唑。
• Microwave-assisted synthesis of 3,5-disubstituted isoxazoles and evaluation of their anti-ageing activity
  作者：Maria Koufaki、Theano Fotopoulou、Marianna Kapetanou、Georgios A. Heropoulos、Efstathios S. Gonos、Niki Chondrogianni

  DOI：10.1016/j.ejmech.2014.06.046

  日期：2014.8

  One-pot uncatalysed microwave-assisted 1,3-dipolar cycloaddition reactions between in situ generated nitrile oxides and alkynes bearing protected antioxidant substituents, were regioselectively afforded 3,5-disubstituted isoxazoles. The yields were moderate, based on the starting aldehydes, while the reaction times were in general shorter than those reported in the literature. The cytoprotective and anti-ageing effect of the final deprotected compounds was evaluated in vitro, on cellular survival following oxidative challenge and in vivo, on organismal longevity using the nematode Caenorhabditis elegans. The activity of the isoxazole analogues depends on the nature and the number of the antioxidant substituents. Analogue 17 bearing a phenolic group and a 6-OH-chroman group is a promising anti-ageing agent, since it increased survival of human primary fibroblasts following treatment with H2O2 and extended C. elegans lifespan.