ethyl 5-(4-(pentyloxy)phenyl)isoxazole-3-carboxylate | 1450606-79-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 5-(4-(pentyloxy)phenyl)isoxazole-3-carboxylate
• 英文别名: Ethyl5-(4-(pentyloxy)phenyl)isoxazole-3-carboxylate；ethyl 5-(4-pentoxyphenyl)-1,2-oxazole-3-carboxylate
• CAS: 1450606-79-7
• 化学式: C₁₇H₂₁NO₄
• 分子量: 303.358
• InChiKey: QUVAOCYYYZWRCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 5-(4-(pentyloxy)phenyl)isoxazole-3-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以74%的产率得到5-(4-pentyloxyphenyl)isoxazole-3-carboxylic acid
  参考文献：
  名称：

  3-Carboxamido-5-aryl-isoxazoles as new CB2 agonists for the treatment of colitis

  摘要：

  Recent investigations showed that anandamide, the main endogenous ligand of CB1 and CB2 cannabinoid receptors, possesses analgesic, antidepressant and anti-inflammatory effects. In the perspective to treat inflammatory bowel disease (IBD), our approach was to develop new selective CB2 receptor agonists without psychotropic side effects associated to CB1 receptors. In this purpose, a new series of 3-carboxamido-5-aryl-isoxazoles, never described previously as CB2 receptor agonists, was designed, synthesized and evaluated for their biological activity. The pharmacological results have identified great selective CB2 agonists with in vivo anti-inflammatory activity in a DSS-induced acute colitis mouse model. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.010
• 作为产物：
  描述：

  1-[4-(戊基氧基)苯基]乙酮 在 盐酸羟胺 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 ethyl 5-(4-(pentyloxy)phenyl)isoxazole-3-carboxylate
  参考文献：
  名称：

  3-Carboxamido-5-aryl-isoxazoles as new CB2 agonists for the treatment of colitis

  摘要：

  Recent investigations showed that anandamide, the main endogenous ligand of CB1 and CB2 cannabinoid receptors, possesses analgesic, antidepressant and anti-inflammatory effects. In the perspective to treat inflammatory bowel disease (IBD), our approach was to develop new selective CB2 receptor agonists without psychotropic side effects associated to CB1 receptors. In this purpose, a new series of 3-carboxamido-5-aryl-isoxazoles, never described previously as CB2 receptor agonists, was designed, synthesized and evaluated for their biological activity. The pharmacological results have identified great selective CB2 agonists with in vivo anti-inflammatory activity in a DSS-induced acute colitis mouse model. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.010

文献信息

• Mechanochemistry Enabled Construction of Isoxazole Skeleton <i>via</i> CuO Nanoparticles Catalyzed Intermolecular Dehydrohalogenative Annulation
  作者：Murugan Vadivelu、Sugirdha Sampath、Kesavan Muthu、Kesavan Karthikeyan、Chandrasekar Praveen

  DOI：10.1002/adsc.202100730

  日期：2021.11.9

  accomplished. This chemistry is operative under the cooperative catalysis of cupric oxide nanoparticles (<50 nm) and DABCO. The key beneficial aspects of this protocol include: (i) broad substrate scope, (ii) no vigorous work-up, (iii) short reaction time, (iv) solvent-free condition, (v) commercial viability of substrates/reagents (vi) good chemical yields and selectivity. The other merit of this chemistry

  通过在机械化学设置下将β-乙烯基卤化物和α-硝基羰基化合物配对，完成了异恶唑环化的脱卤化氢方法。这种化学反应在氧化铜纳米粒子 (<50 nm) 和 DABCO 的协同催化下起作用。该协议的主要有益方面包括：（i）广泛的底物范围，（ii）没有剧烈的后处理，（iii）反应时间短，（iv）无溶剂条件，（v）底物/试剂的商业可行性（ vi) 良好的化学产率和选择性。这种化学反应的另一个优点是反应后 CuO 可以很容易地回收和再利用，六次运行的催化活性没有太大的下降。由于不受 β-乙烯基卤化物的限制，验证条件也对炔烃开放，用于制备异恶唑，
• Effect of Aqueous Polyethylene Glycol on 1,3-Dipolar Cycloaddition of Benzoylnitromethane/Ethyl 2-Nitroacetate with Dipolarophiles: Green Synthesis of Isoxazoles and Isoxazolines
  作者：R. Gangadhara Chary、G. Rajeshwar Reddy、Y. S. S. Ganesh、K. Vara Prasad、Akula Raghunadh、T. Krishna、Soumita Mukherjee、Manojit Pal

  DOI：10.1002/adsc.201300712

  日期：2014.1.13

  A 1:1 mixture of water‐polyethylene glycol (PEG) facilitated the 1,3‐dipolar cycloaddition of benzoylnitromethane/ethyl 2‐nitroacetate with terminal alkynes or alkenes leading to isoxazoles or isoxazolines under green conditions. The methodology is free from the use of any base, catalyst, dehydrating agent or hazardous solvent.

  水与聚乙二醇（PEG）的1：1混合物有助于在绿色条件下将苯甲酰基硝基甲烷/ 2-硝基乙酸乙酯与末端炔烃或烯烃进行1,3-偶极环加成反应，生成异恶唑或异恶唑啉。该方法无需使用任何碱，催化剂，脱水剂或有害溶剂。
• 3-Carboxamido-5-aryl-isoxazoles as new CB2 agonists for the treatment of colitis
  作者：Aurélien Tourteau、Virginie Andrzejak、Mathilde Body-Malapel、Lucas Lemaire、Amélie Lemoine、Roxane Mansouri、Madjid Djouina、Nicolas Renault、Jamal El Bakali、Pierre Desreumaux、Giulio G. Muccioli、Didier M. Lambert、Philippe Chavatte、Benoît Rigo、Natascha Leleu-Chavain、Régis Millet

  DOI：10.1016/j.bmc.2013.06.010

  日期：2013.9

  Recent investigations showed that anandamide, the main endogenous ligand of CB1 and CB2 cannabinoid receptors, possesses analgesic, antidepressant and anti-inflammatory effects. In the perspective to treat inflammatory bowel disease (IBD), our approach was to develop new selective CB2 receptor agonists without psychotropic side effects associated to CB1 receptors. In this purpose, a new series of 3-carboxamido-5-aryl-isoxazoles, never described previously as CB2 receptor agonists, was designed, synthesized and evaluated for their biological activity. The pharmacological results have identified great selective CB2 agonists with in vivo anti-inflammatory activity in a DSS-induced acute colitis mouse model. (C) 2013 Elsevier Ltd. All rights reserved.