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

中文名称
——
中文别名
——
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
5-(4-chlorophenyl)-3-(4-methoxyphenyl)-4,5-dihydroisoxazole化学式
CAS
107095-25-0
化学式
C16H14ClNO2
mdl
——
分子量
287.746
InChiKey
LKRJFARLDIRERF-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

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-dihydroisoxazolemanganese(IV) oxide 、 magnesium sulfate 作用下, 以 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
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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:——
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