(3-(4-hydroxylphenyl)isoxazol-5-yl)methanol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (3-(4-hydroxylphenyl)isoxazol-5-yl)methanol
• 英文别名: 3-(4-hydroxyphenylisoxazol-5-yl)methanol；4-(5-Hydroxymethyl-isoxazol-3-yl)-phenol；4-[5-(hydroxymethyl)-1,2-oxazol-3-yl]phenol
• 化学式: C₁₀H₉NO₃
• 分子量: 191.186
• InChiKey: GNNWTBWWYRFPGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  66.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,6-二氯苄基溴 、 (3-(4-hydroxylphenyl)isoxazol-5-yl)methanol 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以15.9 %的产率得到[3-[4-[(2,6-Dichlorophenyl)methoxy]phenyl]-1,2-oxazol-5-yl]methanol
  参考文献：
  名称：

  WO2023/235384

  摘要：

  公开号：
• 作为产物：
  描述：

  对甲氧基苯甲醛肟 在 三氟二甲基硫醚络合物 、 chloroamine-T 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 24.75h， 生成 (3-(4-hydroxylphenyl)isoxazol-5-yl)methanol
  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。
• One-Pot Synthesis of (3-Phenylisoxazol-5-yl)methanol Derivatives Under Ultrasound
  作者：Chuansheng Shen、Yumin Zhang、Yuanming Gan、Tianqi Zhao、Qiang Gu

  DOI：10.2174/157017811795371467

  日期：2011.5.1

  An ultrasonic-assisted, one-pot, efficient, convenient procedure for the synthesis of (3-phenylisoxazol-5- yl)methanol derivatives has been developed. (3-Phenylisoxazol-5-yl)-methanol derivatives with biological and pharmaceutical property have been synthesized in moderate to excellent yields. The synthetic methods possess the advantages of high yield, facile operation process and shorter reaction time, and so on.

  本研究开发了一种超声波辅助、一锅合成、高效、简便的（3-苯基异恶唑-5-基）甲醇衍生物的方法。合成出的(3-苯基异恶唑-5-基)甲醇衍生物具有适度到极佳的产率，并具有生物和医药特性。这些合成方法具有产率高、操作过程简便、反应时间短等优点。
• SUBSTITUTED AZOLE DERIVATIVES, PHARMACEUTICAL COMPOSITION CONTAINING THE DERIVATIVES, AND METHOD FOR TREATING PARKINSON'S DISEASE USING THE SAME
  申请人：Park Cheol-Hyoung

  公开号：US20110301150A1

  公开（公告）日：2011-12-08

  Provided are a substituted azole derivative and pharmaceutically acceptable salts thereof, a pharmaceutical composition including an effective amount of the derivative, and a method for treating Parkinson's disease in a mammal including administering an effective amount of the compound to the mammal. The azole derivative of the following Formula (I) and pharmaceutically useful salts thereof have an efficacy against Parkinson's disease from inhibitory effects of the activity of MAO-B.

  提供了一种替代的唑类衍生物及其药学上可接受的盐，一种包括有效量衍生物的制药组合物，以及一种治疗哺乳动物帕金森病的方法，包括向哺乳动物施用化合物的有效量。以下公式（I）的唑类衍生物及其药学上有用的盐具有抗帕金森病的功效，来自于对MAO-B活性的抑制作用。
• Substituted azole derivatives, pharmaceutical composition containing the derivatives, and method for treating Parkinson's disease using the same
  申请人：Park Cheol-Hyoung

  公开号：US08828992B2

  公开（公告）日：2014-09-09

  Provided are a substituted azole derivative and pharmaceutically acceptable salts thereof, a pharmaceutical composition including an effective amount of the derivative, and a method for treating Parkinson's disease in a mammal including administering an effective amount of the compound to the mammal. The azole derivative of the following Formula (I) and pharmaceutically useful salts thereof have an efficacy against Parkinson's disease from inhibitory effects of the activity of MAO-B.

  提供了一种替代的唑类衍生物及其药物可接受的盐，一种包括有效量的该衍生物的制药组合物，以及一种治疗哺乳动物帕金森病的方法，包括向哺乳动物投与有效量的该化合物。以下公式（I）的唑类衍生物及其药物可用盐对MAO-B活性的抑制作用具有有效性，可用于治疗帕金森病。
• One pot solid phase synthesis of isoxazolines
  作者：B.B. Shankar、D.Y. Yang、S. Girton、A.K. Ganguly

  DOI：10.1016/s0040-4039(98)00237-8

  日期：1998.4

  1,3 Dipolar cycloadditions of nitrile oxides generated in situ on solid phase in the presence of a variety of dipolaraphiles provided a library of isoxazolines and isoxazoles. (C) 1998 Elsevier Science Ltd. All rights reserved.