3,5-bis(4-methoxyphenyl)isoxazole | 52751-67-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,5-bis(4-methoxyphenyl)isoxazole
• 英文别名: 3,5-bis(4-methoxyphenyl)-1,2-oxazole
• CAS: 52751-67-4
• 化学式: C₁₇H₁₅NO₃
• mdl: MFCD08551131
• 分子量: 281.311
• InChiKey: OFUJZKSPFSYMPL-UHFFFAOYSA-N

物化性质

• 熔点：
  138-140 °C(Solv: ethanol (64-17-5))
• 沸点：
  460.5±45.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-bis(4-methoxyphenyl)isoxazole 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 4,4'-(isoxazol-3,5-diyl)diphenol
  参考文献：
  名称：

  Antiproliferative novel isoxazoles: Modeling, virtual screening, synthesis, and bioactivity evaluation

  摘要：

  A series of novel isoxazole derivatives were efficiently synthesized through the adaptation/modification of an in situ synthetic procedure for pyrazoles. All novel compounds were tested against four different cell lines to evaluate their antiproliferative activity. Based on the Hela cells results of this study and previous work, a classification model to predict the anti-proliferative activity of isoxazole and pyrazole derivatives was developed. Random Forest modeling was used in view of the development of an accurate and reliable model that was subsequently validated. A virtual screening study was then proposed for the design of novel active derivatives. Compounds 9 and 11 demonstrated significant cytostatic activity; the fused isoxazole derivative 18 and the virtually proposed compound 2v, were proved at least 10 times more potent as compared to compound 9, with IC50 values near and below 1 mu M. In conclusion, a new series of isoxazoles was exploited with some of them exhibiting promising cytostatic activities. Further studies on the substitution pattern of the isoxazole core can potentially provide compounds with cytostatic action at the nM scale. In this direction the in silica approach described herein can also be used to screen existing databases to identify derivatives with anticipated activity. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.011
• 作为产物：
  描述：

  4,4’-二甲氧基查耳酮 在 盐酸羟胺 、 sodium acetate 、 2-碘酰基苯甲酸 作用下， 以 氯仿 为溶剂， 反应 4.0h， 以88%的产率得到3,5-bis(4-methoxyphenyl)isoxazole
  参考文献：
  名称：

  邻碘氧基苯甲酸介导合成 3,5-二芳基异恶唑和异恶唑-3-羧酸

  摘要：

  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

  DOI：

  10.1080/00397911.2013.854916

文献信息

• Reactions of 5-substituted 3-alkyl- and 3-aryl-isoxazoles with tetrasulfur tetranitride antimony pentachloride complex (S4N4·SbCl5): complete regioselective formation of 4-substituted 3-acyl- and 3-aroyl-1,2,5-thiadiazoles and their mechanism of formation
  作者：Kil-Joong Kim、Kyongtae Kim

  DOI：10.1039/a802408a

  日期：——

  The reactions of 3-alkyl- 5a–f, 3-aryl- 5g–m, 3-acylamido- 5n,p, 3-benzamido- 5o and 3-arylamino- 5q -5-alkyl- and -5-aryl-isoxazoles with tetrasulfur tetranitride antimony pentachloride complex (S4N4·SbCl5) in toluene at 90 °C to reflux temperature give 3-acyl- 6a–c, e, n–q and 3-aroyl-4-substituted-1,2,5-thiadiazoles 6d, f–m in 13 to 61% yields as single isomers. The same reactions of 3,4-dimethyl-

  3-烷基-5a-f，3-芳基-5g-m，3-酰基酰胺基-5n，p，3-苯甲酰胺基-5o和3-芳基氨基-5q -5-烷基-和-5-芳基-异恶唑的反应四氮化四锑五氯化锑（S 4 N 4 ·SbCl 5）在90°C的甲苯中至回流温度，得到13-61％的3-酰基-6a-c，e，n-q和3-芳酰基-4-取代的1,2,5-噻二唑6d，f-m产生为单一异构体。3,4-二甲基-5s，5v，4-乙基-3-甲基-5t -5-烷基-和/或5-芳基-异恶唑在相同条件下的相同反应得到3-（1-乙酰基-1-氯乙基）-8a，3-（1-苯甲酰基-1-氯丙基）-8b，3-（1-苯甲酰基-1-氯乙基）-8d或3-（1-苯甲酰基-1-氯乙基）-4-甲基- 1,2,5-噻二唑8c是一种新型的1,2,5-噻二唑衍生物。另外，在相同条件下，与具有供电子取代基例如甲基，4-甲基苯基和4-甲氧基苯基的5-芳基-4-溴异恶唑（5，w，y，z）在相同条件下反应，得到3-芳酰基。
• CATALYTIC REACTION
  申请人：National Tsing Hua University

  公开号：US20150259305A1

  公开（公告）日：2015-09-17

  A catalytic reaction comprises several steps: providing a catalyst, wherein the catalyst is metal or metal oxide particles and at least have 110} crystal plane; using the catalyst when performing a cycloaddition reaction. By using the catalyst with high reactivity, reaction rate is dramatically promoted.

  催化反应包括几个步骤：提供一种催化剂，其中催化剂是金属或金属氧化物颗粒，并且至少具有110}晶面；在执行环加成反应时使用该催化剂。通过使用高活性的催化剂，反应速率得到了显著提升。
• 17BETA-HYDROXYSTEROID DEHYDROGENASE TYPE 1 INHIBITORS FOR THE TREATMENT OF HORMONE-RELATED DISEASES
  申请人：Hartmann Rolf

  公开号：US20110046147A1

  公开（公告）日：2011-02-24

  The invention relates to 17beta-hydroxysteroid dehydrogenase type 1 (17betaHSD1) inhibitors, the preparation thereof and the use thereof for the treatment and prophylaxis of hormone-related, especially estrogen-related or androgen-related, diseases.

  该发明涉及17beta-羟基类固醇脱氢酶1型（17betaHSD1）抑制剂，其制备以及用于治疗和预防激素相关疾病，特别是雌激素相关或雄激素相关疾病的用途。
• Aerobic Oxidative Synthesis of 3,5-disubstituted Isoxazoles Directly from α,β-unsaturated Ketones
  作者：Zheng Li、Gong Wen、Rugang Fu、Jingya Yang

  DOI：10.3184/174751916x14744677622496

  日期：2016.10

  Using an efficient aerobic oxidative method, the synthesis of ten 3,5-disubstituted isoxazoles by treatment of α,β-unsaturated ketones with hydroxylamine and NaOH at room temperature has been achieved.

  采用高效的好氧氧化方法，在室温下用羟胺和NaOH处理α,β-不饱和酮，合成了10个3,5-二取代异恶唑。
• A Novel NO Insertion into Cyclopropane Ring by Use of NOBF₄· Formation of 2-Isoxazolines
  作者：Nobuyuki Ichinose、Kazuhiko Mizuno、Toshiyuki Tamai、Yoshio Otsuji

  DOI：10.1246/cl.1988.233

  日期：1988.2.5

  of 1,2-diarylcyclopropanes with NOBF4 in CH3CN gave 3,5-diaryl-2-isoxazolines in good yields. For unsymmetrically substituted cyclopropanes, the mixtures of two isomeric isoxazolines were obtained. The mechanism and regioselectivity in this NO insertion into the cyclopropane ring are described.

  1,2-二芳基环丙烷与 NOBF4 在 CH3CN 中的反应以良好的收率得到 3,5-二芳基-2-异恶唑啉。对于不对称取代的环丙烷，获得了两种异构异恶唑啉的混合物。描述了这种 NO 插入环丙烷环的机制和区域选择性。