5-(4-chlorophenyl)-3-(4-methoxyphenyl)-4,5-dihydroisoxazole | 107095-25-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(4-chlorophenyl)-3-(4-methoxyphenyl)-4,5-dihydroisoxazole
• 英文别名: 3-(4-methoxyphenyl)-5-(4-chlorophenyl)-2-isoxazoline；5-(4-Chlorophenyl)-3-(4-methoxyphenyl)-4,5-dihydro-1,2-oxazole
• CAS: 107095-25-0
• 化学式: C₁₆H₁₄ClNO₂
• 分子量: 287.746
• InChiKey: LKRJFARLDIRERF-UHFFFAOYSA-N

物化性质

• 熔点：
  156 °C(Solv: methanol (67-56-1))
• 沸点：
  412.2±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-chlorophenyl)-3-(4-methoxyphenyl)-4,5-dihydroisoxazole 在 manganese(IV) oxide 、 magnesium sulfate 作用下， 以 苯 为溶剂， 反应 1.5h， 以70%的产率得到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
• 作为产物：
  描述：

  4'-methoxy-4-chlorochalcone 在 盐酸羟胺 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以94%的产率得到5-(4-chlorophenyl)-3-(4-methoxyphenyl)-4,5-dihydroisoxazole
  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

• 9,10-Dicyanoanthracene-Sensitized NO Insertion into Cyclopropane Ring via Photoinduced Electron Transfer
  作者：Nobuyuki Ichinose、Kazuhiko Mizuno、Katsuhiko Yoshida、Yoshio Otsuji

  DOI：10.1246/cl.1988.723

  日期：1988.4.5

  9,10-Dicyanoanthracene-sensitized photoreaction of electron-rich 1,2-diarylcyclopropanes with NO in acetonitrile afforded 3,5-diaryl-2-isoxazolines in good yields. The cyclopropanes bearing different aryl-substituents gave a mixture of two isomeric 2-isoxazolines. Mechanistic features of this reaction are described.

  富电子的1,2-二芳基环丙烷与NO在乙腈中通过9,10-二氰基蒽敏化的光反应，以良好的产率得到了3,5-二芳基-2-异恶唑啉。带有不同芳基取代基的环丙烷生成了两种异构的2-异恶唑啉的混合物。该反应的机理特征被详细描述。
• Insertion of nitrogen oxide and nitrosonium ion into the cyclopropane ring: a new route to 2-isoxazolines and its mechanistic studies
  作者：Kazuhiko Mizuno、Nobuyuki Ichinose、Toshiyuki Tamai、Yoshio Otsuji

  DOI：10.1021/jo00043a026

  日期：1992.8

  The 9,10-dicyanoanthracene (DCA)-sensitized photoreaction of 1,2-diarylcyclopropanes 1a-d in nitrogen oxide (NO)-saturated CH3CN afforded 3,5-diaryl-2-isoxazolines 2a-d in excellent yields. The reaction of 1a-d with NOBF4 or with a mixture of NO and O2 in CH3CN also afforded 2a-d or 2a-b. These reactions proceed via the attack of NO on the radical cation of 1, which is formed by electron transfer from 1 to 1DCA* or NO+. The reaction of 1-alkyl-2-arylcyclopropanes with NOBF4 afforded mixtures of 3-alkyl-5-aryl-2-isoxazolines and 4-alkyl-5-aryl-2-isoxazolines via the direct attack of NO+ on the cyclopropane rings. The reaction of 1,1,2,2-tetraphenylcyclopropane with NOBF4 afforded 2,3,5,5-tetraphenyl-2-isoxazolinium tetrafluoroborate via the migration of the phenyl group to nitrogen.
• A Gloria, Journal fur praktische Chemie (Leipzig 1954), 1986, vol. 328, # 2, p. 245 - 252
  作者：A Gloria

  DOI：——

  日期：——
• ALVAREZ-BUILLA J.; BENITO V. L.; QUINTANILLA G., J. PRAKT. CHEM., 328,(1986) N 2, 245-252
  作者：ALVAREZ-BUILLA J.、 BENITO V. L.、 QUINTANILLA G.

  DOI：——

  日期：——
• ICHINOSE, NOBUYUKI;MIZUNO, KAZUHIKO;YOSHIDA, KATSUHIKO;OTSUJI, YOSHIO, CHEM. LETT.,(1988) N 4, 723-724
  作者：ICHINOSE, NOBUYUKI、MIZUNO, KAZUHIKO、YOSHIDA, KATSUHIKO、OTSUJI, YOSHIO

  DOI：——

  日期：——