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3-(4-ethynylphenyl)-5-phenyl-1,2,4-oxadiazole | 957470-95-0

中文名称
——
中文别名
——
英文名称
3-(4-ethynylphenyl)-5-phenyl-1,2,4-oxadiazole
英文别名
——
3-(4-ethynylphenyl)-5-phenyl-1,2,4-oxadiazole化学式
CAS
957470-95-0
化学式
C16H10N2O
mdl
——
分子量
246.268
InChiKey
RPLQYHXCXPDWRW-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

计算性质

  • 辛醇/水分配系数(LogP):
    3.38
  • 重原子数:
    19.0
  • 可旋转键数:
    2.0
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.0
  • 拓扑面积:
    38.92
  • 氢给体数:
    0.0
  • 氢受体数:
    3.0

反应信息

  • 作为反应物:
    描述:
    ethyl 4-azido-6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-α-D-erythro-hex-2-enopyranoside3-(4-ethynylphenyl)-5-phenyl-1,2,4-oxadiazole 在 copper diacetate 、 sodium ascorbate 作用下, 以 二氯甲烷 为溶剂, 反应 20.0h, 以80%的产率得到ethyl 6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-4-{4-[4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl]-1H-1,2,3-triazol-4-yl}-α-D-erythro-hex-2-enopyranoside
    参考文献:
    名称:
    Synthesis of Some Unusual (1,2,4-Oxadiazole)-Linked Hexenopyranosides and Mannopyranosides
    摘要:
    A copper-catalyzed reaction of propargyl 4,6-di-O-acetyl-2,3-dideoxy-alpha-D-erythro-hex-2-enopyranoside with 3-(4-azidophenyl)-1,2,4-oxadiazoles gave the corresponding hexenopyranosides bearing an 1,2,4-oxadiazole subunit in the aglyconic part of the molecule. The same reaction between ethyl 4-azido-2,3,4-trideoxy-alpha-D-erythro-hex-2-enopyranoside and acetylenic 1,2,4-oxadiazoles afforded the corresponding hexenopyranosides carrying a triazole and a 1,2,4-oxadiazole ring at C-4 of the carbohydrate. Combination of the two sequences gave hexenopyranosides displaying two 1,2,4-oxadiazole subunits, each one being embedded in the C-1 and C-4 frameworks, of the carbohydrate moiety. A simple dihydroxylation reaction of these unsaturated carbohydrates yielded a series of mannopyranosides bearing one or two 1,2,4-oxadiazole subunits at C-1 or C-4. These new compounds were evaluated for their cytotoxic activities against two cell strains: NCI-H-292 (lung carcinoma) and Hep-2 (larynx carcinoma), some of them presenting impressive cell growth inhibitions.
    DOI:
    10.1080/07328300802120901
  • 作为产物:
    参考文献:
    名称:
    Synthesis of glycosyl-triazole linked 1,2,4-oxadiazoles
    摘要:
    The synthesis of four different types of oxadiazoles containing a terminal acetylenic group is described. Reaction of these oxadiazoles with various azidoglycosides via a copper-catalyzed [3+2] cycloaddition ('click chemistry') afforded the corresponding glycosyl-triazole linked 1,2,4-oxadiazoles in good yields. (C) 2007 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.carres.2007.07.011
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