3-(4-chlorophenyl)-5-(4-hydroxyphenyl)isoxazole | 748771-32-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4-chlorophenyl)-5-(4-hydroxyphenyl)isoxazole
• 英文别名: 4-[3-(4-Chlorophenyl)-1,2-oxazol-5-yl]phenol；4-[3-(4-chlorophenyl)-1,2-oxazol-5-yl]phenol
• CAS: 748771-32-6
• 化学式: C₁₅H₁₀ClNO₂
• 分子量: 271.703
• InChiKey: VOHVTJHZBZZICP-UHFFFAOYSA-N

物化性质

• 沸点：
  464.8±35.0 °C(Predicted)
• 密度：
  1.316±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 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：

  氯乙酸 、 3-(4-chlorophenyl)-5-(4-hydroxyphenyl)isoxazole 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以70.52%的产率得到2-(4-(3-(4-chlorophenyl)isoxazol-5-yl)phenoxy)acetic acid
  参考文献：
  名称：

  某些新型取代苯基异恶唑苯氧基乙酸衍生物的合成及体内降血脂活性

  摘要：

  进行本研究以评价Triton诱导的高脂血症大鼠体内一系列新的2-甲基-2-（取代的苯基异恶唑）苯氧基乙酸衍生物的体内降血脂活性。与标准药物非诺贝特相比，新合成的化合物5a，5d和5g血清TCH，TG，LDL和VLDL显着降低，同时血清HDL水平升高。与对照组相比，治疗组的动脉粥样硬化指数也显着降低，而保护活性的百分比提高。

  DOI：

  10.1016/j.bmcl.2014.03.030
• 作为产物：
  描述：

  Alpha,4-二氯苯甲醛肟 在 manganese(IV) oxide 、 氢溴酸 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 3-(4-chlorophenyl)-5-(4-hydroxyphenyl)isoxazole
  参考文献：
  名称：

  3,5-diarylisoxazoles: A New Entry to Soft Crystal Phase

  摘要：

  This work describes the synthesis and characterization of a new liquid-crystalline compounds based on isoxazoles. Classical synthetic methodologies were employed in the preparation of this compounds, and the [3+2] 1,3-dipolar cycloaddition was the key step to prepare isoxazolines as precursors to isoxazoles. The structural and thermal characterization was performed using H-1 and C-13 NMR techniques, polarized-light optical microscopy and differential scanning calorimetry. Compounds 7a-e displayed the SmA mesophase. Soft crystal phase (CrE) was observed for compounds 7a and 7b containing chlorine and bromine atoms. For 7e containing a nitro group crystal phases below SmA mesophase were also observed.

  DOI：

  10.1080/15421406.2015.1030975

文献信息

• Synthesis of some novel substituted phenylisoxazol phenoxy 2-methylpropanoic acids and there in vivo hypolipidemic activity
  作者：Santosh N. Mokale、Pritam N. Dube、Manjusha C. Nevase、Nikhil S. Sakle、Vishakha R. Shelke、Swati A. Bhavale、Afreen Begum

  DOI：10.1007/s00044-015-1498-2

  日期：2016.3

  The novel series of phenylisoxazol phenoxy 2-methylpropanoic acid derivatives were synthesized and evaluated for their in vivo hypolipidemic activity by triton WR-1339-induced hyperlipidemia in rats. The newly synthesized compounds 5a and 5i showed significant decrease in the serum TCH, TG, LDL and VLDL along with an increase in serum HDL levels as compared to standard drug Fenofibrate. The treated

  合成了一系列新的苯基异恶唑苯氧基2-甲基丙酸衍生物，并通过Triton WR-1339诱导的大鼠高脂血症评估了它们的体内降血脂活性。与标准药物非诺贝特相比，新合成的化合物5a和5i血清TCH，TG，LDL和VLDL显着降低，同时血清HDL水平升高。与胆固醇诱导的高脂血症对照组相比，治疗组的动脉粥样硬化指数，TC：HDL风险比也显着降低。这些分子确实具有发展为降血脂分子的潜力。
• 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.
• Synthesis and in-vivo hypolipidemic activity of some novel substituted phenyl isoxazol phenoxy acetic acid derivatives
  作者：Santosh N. Mokale、Manjusha C. Nevase、Nikhil S. Sakle、Pritam N. Dube、Vishakha R. Shelke、Swati A. Bhavale、Afreen Begum

  DOI：10.1016/j.bmcl.2014.03.030

  日期：2014.5

  The present study was undertaken to evaluate in-vivo hypolipidemic activity of a novel series of 2-methyl-2-(substituted phenyl isoxazol)phenoxyacetic acid derivatives by triton induced hyperlipidemia in rats. The newly synthesized compounds 5a, 5d and 5g showed significant decrease in the serum TCH, TG, LDL and VLDL along with an increase in serum HDL levels as compared to standard drug Fenofibrate

  进行本研究以评价Triton诱导的高脂血症大鼠体内一系列新的2-甲基-2-（取代的苯基异恶唑）苯氧基乙酸衍生物的体内降血脂活性。与标准药物非诺贝特相比，新合成的化合物5a，5d和5g血清TCH，TG，LDL和VLDL显着降低，同时血清HDL水平升高。与对照组相比，治疗组的动脉粥样硬化指数也显着降低，而保护活性的百分比提高。
• 3,5-diarylisoxazoles: A New Entry to Soft Crystal Phase
  作者：Rafaela R. da Rosa、Irwing S. Brose、Guilherme D. Vilela、Aloir A. Merlo

  DOI：10.1080/15421406.2015.1030975

  日期：2015.5.3

  This work describes the synthesis and characterization of a new liquid-crystalline compounds based on isoxazoles. Classical synthetic methodologies were employed in the preparation of this compounds, and the [3+2] 1,3-dipolar cycloaddition was the key step to prepare isoxazolines as precursors to isoxazoles. The structural and thermal characterization was performed using H-1 and C-13 NMR techniques, polarized-light optical microscopy and differential scanning calorimetry. Compounds 7a-e displayed the SmA mesophase. Soft crystal phase (CrE) was observed for compounds 7a and 7b containing chlorine and bromine atoms. For 7e containing a nitro group crystal phases below SmA mesophase were also observed.