5-(4-氯苯基)-3-(4-甲氧基苯基)-1,2-恶唑 | 24097-20-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 5-(4-氯苯基)-3-(4-甲氧基苯基)-1,2-恶唑
• 英文名称: 5-(4-chlorophenyl)-3-(4-methoxyphenyl)isoxazole
• 英文别名: 5-(4-chloro-phenyl)-3-(4-methoxy-phenyl)-isoxazole；5-(4-Chlorophenyl)-3-(4-methoxyphenyl)-1,2-oxazole
• CAS: 24097-20-9
• 化学式: C₁₆H₁₂ClNO₂
• 分子量: 285.73
• InChiKey: UNUIPRJEZZQZLF-UHFFFAOYSA-N

物化性质

• 熔点：
  185-186 °C
• 沸点：
  453.0±40.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  5-(4-氯苯基)-3-(4-甲氧基苯基)-1,2-恶唑 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 4-[5-(4-chloro-phenyl)-isoxazol-3-yl]-phenol
  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'-methoxy-4-chlorochalcone 在 manganese(IV) oxide 、 盐酸羟胺 、 magnesium sulfate 、 potassium hydroxide 作用下， 以 乙醇 、 苯 为溶剂， 反应 25.5h， 生成 5-(4-氯苯基)-3-(4-甲氧基苯基)-1,2-恶唑
  参考文献：
  名称：

  Exploration of the SAR of anti-invasive chalcones: Synthesis and biological evaluation of conformationally restricted analogues

  摘要：

  In order to get a clearer view on the active geometry of anti-invasive chalcones, we have prepared a number of isoxazoles and related substances as conformationally restrained mimics of 1,3-diarylpropenones, and also of (Z)-stilbenes. In vitro anti-invasive activity data for 3,5-isoxazoles and 4,5-isoxazoles, together with an in silico geometrical comparison, point towards an active conformation for chalcones more resembling their s-trans geometry than the s-cis counterpart. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.069

文献信息

• <i>o</i>-Iodoxy Benzoic Acid–Mediated Synthesis of 3,5-Diarylisoxazoles and Isoxazole-3-carboxylic Acids
  作者：Vidya G. Desai、Sneha R. Naik、Kashinath L. Dhumaskar

  DOI：10.1080/00397911.2013.854916

  日期：2014.5.19

  Abstract A new, convenient, ecofriendly synthesis of 3,5-diarylisoxazoles is reported from α,β-unsaturated ketoximes. Similarly, a novel synthesis of isoxazole carboxylic acids is also reported. Both the methods use efficient, environmentally friendly, and nontoxic iodoxybenzoic acid (IBX) as an oxidative cyclizing reagent. Easy procedure, environmentally benign reaction conditions, and nontoxicity

  摘要 报道了一种以 α,β-不饱和酮肟为原料合成 3,5-二芳基异恶唑的新型、方便、环保的方法。类似地，还报道了异恶唑羧酸的新合成。这两种方法都使用高效、环保且无毒的碘氧基苯甲酸 (IBX) 作为氧化环化试剂。简单的程序、环境友好的反应条件和无毒是该方法的优点。图形概要
• Synthesis of 3,5-diarylisoxazoles under solvent-free conditions using iodobenzene diacetate
  作者：Kondapalli Venkata Gowri Chandra Sekhar、Thripuraribhatla Venkata Naga Varun Sasank、Hunsur Nagendra Nagesh、Narva Suresh、Kalaga Mahalakshmi Naidu、Amaroju Suresh

  DOI：10.1016/j.cclet.2013.07.022

  日期：2013.12

  Abstract A simple and efficient method has been developed for conversion of chalcone oximes to 3,5-diaryl isoxazoles in excellent yields under solvent-free conditions. The synthesized compounds were characterized by infrared spectroscopy, 1 H NMR, 13 C NMR and HRMS.

  摘要研究了一种简单有效的方法，可在无溶剂条件下以优异的收率将查尔酮肟转化为3,5-二芳基异恶唑。合成的化合物通过红外光谱，1 H NMR，13 C NMR和HRMS进行表征。
• New synthesis of isoxazoles from 1,4-dianions of oximes having an .alpha. hydrogen. Mass spectrometry
  作者：Charles F. Beam、Morgan C. D. Dyer、Richard A. Schwarz、Charles R. Hauser

  DOI：10.1021/jo00831a020

  日期：1970.6
• 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
  作者：Michele A Weidner-Wells、Todd C Henninger、Stephanie A Fraga-Spano、Christine M Boggs、Michele Matheis、David M Ritchie、Dennis C Argentieri、Michael P Wachter、Dennis J Hlasta

  DOI：10.1016/j.bmcl.2004.05.080

  日期：2004.8

  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.
• Exploration of the SAR of anti-invasive chalcones: Synthesis and biological evaluation of conformationally restricted analogues
  作者：Bart I. Roman、Tine De Ryck、Laura Dierickx、Barbara W.A. Vanhoecke、Alan R. Katritzky、Marc Bracke、Christian V. Stevens

  DOI：10.1016/j.bmc.2012.05.069

  日期：2012.8

  In order to get a clearer view on the active geometry of anti-invasive chalcones, we have prepared a number of isoxazoles and related substances as conformationally restrained mimics of 1,3-diarylpropenones, and also of (Z)-stilbenes. In vitro anti-invasive activity data for 3,5-isoxazoles and 4,5-isoxazoles, together with an in silico geometrical comparison, point towards an active conformation for chalcones more resembling their s-trans geometry than the s-cis counterpart. (C) 2012 Elsevier Ltd. All rights reserved.