4-(5-phenylisoxazol-3-yl) phenol | 22439-72-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(5-phenylisoxazol-3-yl) phenol
• 英文别名: 4-(5-Phenyl-1,2-oxazol-3-yl)phenol；4-(5-phenyl-1,2-oxazol-3-yl)phenol
• CAS: 22439-72-1
• 化学式: C₁₅H₁₁NO₂
• 分子量: 237.258
• InChiKey: NPBXJZXASLEMJN-UHFFFAOYSA-N

物化性质

• 熔点：
  197 °C(Solv: ethanol (64-17-5))
• 沸点：
  441.4±30.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(5-phenylisoxazol-3-yl) phenol 、 N,N-二甲基-3-氯丙胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N,N-dimethyl-3-[4-(5-phenyl-1,2-oxazol-3-yl)phenoxy]propan-1-amine
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 3,5-diarylisoxazoles and 3,5-diaryl-1,2,4-oxadiazoles, novel classes of small molecule interleukin-8 (IL-8) receptor antagonists

  摘要：

  A novel series of 3,5-diarylisoxazole and 3,5-diaryl-1,2,4-oxadiazole IL-8 antagonists has been identified. These compounds exhibit activity in an IL-8 binding assay as well as in a functional assay of IL-8 induced elastase release from neutrophils. In addition, one of the compounds exhibits oral activity in a rat adjuvant arthritis model. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.080
• 作为产物：
  描述：

  [(4-甲氧苯基)次甲基]氮烷氧化 在 copper(ll) sulfate pentahydrate 、 三氟二甲基硫醚络合物 、 sodium ascorbate 作用下， 以 二氯甲烷 为溶剂， 反应 24.5h， 生成 4-(5-phenylisoxazol-3-yl) phenol
  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

文献信息

• Metal-free DBU promoted regioselective synthesis of isoxazoles and isoxazolines
  作者：Shabber Mohammed、Ram A. Vishwakarma、Sandip B. Bharate

  DOI：10.1039/c4ra14694h

  日期：——

  8-diazabicyclo[5.4.0]undec-7-ene (DBU) promoted regioselective synthesis of 3,5-disubstituted isoxazoles and isoxazolines from aldoximes has been described. This method allows the reaction to proceed efficiently on aldoximes containing unprotected phenolic hydroxyl groups. Furthermore, with the use of higher equivalents of N-chlorosuccinimide, chloro-substituted isoxazoles and isoxazolines were obtained as the

  已经描述了一种新的简单有效的无金属的1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）促进的由醛肟合成的3,5-二取代的异恶唑和异恶唑啉的区域选择性合成。该方法允许反应在含有未保护的酚羟基的醛肟上有效地进行。此外，通过使用较高当量的N-氯代琥珀酰亚胺，通过串联一锅的1，3-偶极环加成，然后进行区域选择性氯化，获得了氯取代的异恶唑和异恶唑啉作为唯一产物。
• Synthesis of new generation triazolyl- and isoxazolyl-containing 6-nitro-2,3-dihydroimidazooxazoles as anti-TB agents: in vitro, structure–activity relationship, pharmacokinetics and in vivo evaluation
  作者：Gurunadham Munagala、Kushalava Reddy Yempalla、Samsher Singh、Sumit Sharma、Nitin Pal Kalia、Vikrant Singh Rajput、Sunil Kumar、Sanghapal D. Sawant、Inshad Ali Khan、Ram A. Vishwakarma、Parvinder Pal Singh

  DOI：10.1039/c5ob00054h

  日期：——

  Promising nitroimidazoloxazole scaffold gives another novel triazolyl-containing 6-nitro-2,3-dihydroimidazooxazole as anti-TB lead.

  有前途的硝基咪唑噁唑骨架提供了另一种新颖的三唑基含有的6-硝基-2,3-二氢咪唑噁唑作为抗结核病的先导化合物。
• [EN] 6-NITRO-2,3-DIHYDROIMIDAZO[2,1-b]OXAZOLES AND A PROCESS FOR THE PREPARATION THEREOF<br/>[FR] 6-NITRO-2,3-DIHYDROIMIDAZO[2,1-B]OXAZOLES ET LEUR PROCÉDÉ DE PRÉPARATION
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2015049693A1

  公开（公告）日：2015-04-09

  The present invention relates to newer generation of triazoles, tetrazoles, isoxazoles, urea and sulphonamide functionalities containing 6-nitro-2, 3-dihydronitroimidazooxazoles agents of formula 1, their method of preparation, and their use as drugs for treating Mycobacterium tuberculosis,MDR-TB and XDR-TB either alone or in combination with other anti-tubercular agents. In the present invention, new generation 6-nitro-2, 3-dihydronitroimidazooxazoles agents also show acceptable pharmacokinetic properties and synergistic or additive effects with known anti-tubercular drugs.

  本发明涉及新一代三唑类、四唑类、异噁唑类、尿素和磺胺类功能团的含有6-硝基-2,3-二氢硝基咪唑噁唑类化合物的制备方法，以及它们作为治疗结核分枝杆菌、耐药结核分枝杆菌和极耐药结核分枝杆菌的药物的用途，可以单独使用，也可以与其他抗结核药物联合使用。在本发明中，新一代6-硝基-2,3-二氢硝基咪唑噁唑类化合物还表现出可接受的药代动力学性质，并与已知的抗结核药物呈现协同或加成效应。
• 一种氨基酸异噁唑酯类化合物及其作为农用杀菌剂的应用
  申请人：湖北科技学院

  公开号：CN117756735A

  公开（公告）日：2024-03-26

  本发明公开了一种氨基酸异噁唑酯类化合物及其作为农用杀菌剂的应用，属于有机化学和农药学技术领域。本发明的氨基酸异噁唑酯类化合物的结构通式如下所示：#imgabs0#本发明的氨基酸异噁唑酯类化合物对水稻纹枯病菌、水稻稻瘟病菌等多种农作物病原真菌具有抑制作用，可用于制备农用杀菌剂。
• 10.1039/d4ob00797b
  作者：Das, Sukanya、Datta, Tanmoy、Sk, Md. Abbasuddin、Roy, Brindaban、Nandi, Raj K.

  DOI：10.1039/d4ob00797b

  日期：——

  A highly effective isoxazole directed ortho C–H alkynylation has been developed. Rhodium(III) catalyzed direct di-(and/or mono) alkynylation using a hypervalent iodine reagent (TIPS-EBX) is reported. The reaction proceeds with a wide substrate scope under benign conditions. Preliminary mechanistic studies support this chelation assisted C–H alkynylation.

  一种高效的异恶唑定向邻位C-H 炔基化反应已被开发出来。据报道，使用高价碘试剂 (TIPS-EBX) 进行铑 ( III ) 催化的直接二（和/或单）炔基化。该反应在良好的条件下以广泛的底物范围进行。初步机制研究支持这种螯合辅助的 C-H 炔基化。