3-[4-(dimethylamino)phenyl]-4H-1,2,4-oxadiazol-5-one | 1178738-59-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-[4-(dimethylamino)phenyl]-4H-1,2,4-oxadiazol-5-one
• CAS: 1178738-59-4
• 化学式: C₁₀H₁₁N₃O₂
• 分子量: 205.216
• InChiKey: NXEHQRGOYIZBSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  53.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  三乙胺 、 3-[4-(dimethylamino)phenyl]-4H-1,2,4-oxadiazol-5-one 在 碘 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以93 %的产率得到3-(4-(dimethylamino)phenyl)-N,N-diethyl-1,2,4-oxadiazol-5-amine
  参考文献：
  名称：

  Tertiary Amines as Temporary Masked Secondary Amines: A Direct Access to 5-Dialkylamino-1,2,4-oxadiazoles from 1,2,4-Oxadiazol-5(4H)-ones

  摘要：

  A novel strategy utilizing tertiary amines as temporary masked secondary amines to synthesize 5-dialkylamino 1,2,4-oxadiazoles via Ph3P-I2 mediated amination of 1,2,4-oxadiazol-5(4H)-ones was developed. A one-step N-dealkylative functionalization of tertiary amines with the 1,2,4-oxadiazole ring enables a convenient access to diverse 5-amino-1,2,4-oxadiazoles. Additionally, orthogonally functionalized piperazine derivatives can be effectively constructed through site-selective reaction of 1,4-dialkylpiperazines or via a sequential N-functionalization of 1-methylpiperazine obviating laborious protection/deprotection steps.

  DOI：

  10.1055/s-0042-1751555
• 作为产物：
  描述：

  4-二甲基氨基-N-羟基苯胺 、 N,N'-羰基二咪唑 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 3-[4-(dimethylamino)phenyl]-4H-1,2,4-oxadiazol-5-one
  参考文献：
  名称：

  NH-acidities and Hammett correlation of 3-para substituted phenyl-1,2,4-oxadiazol-5(4$H)$-ones and 1,2 $\lambda^{4}$3,5-oxathiadiazole 2-oxides in nonaqueous media

  摘要：

  一些3-(对取代苯基)-1,2,4-噁二唑-5(4H)-酮和4-(对取代苯基)-1,2λ^43,5-噻二氮杂烯-2-氧化物的NH酸度在甲醇中通过与甲氧化钠的电位滴定进行测定。根据电位数据计算出的标题化合物的pK_a值通过绘制pK_a值与Hammett σ_p^+常数的关系图来解释，这表明对取代基对苯环造成的结构效应，得到了很好的线性相关性。

  DOI：

  10.3906/kim-1303-46

文献信息

• NH-acidities and Hammett correlation of 3-para substituted phenyl-1,2,4-oxadiazol-5(4$H)$-ones and 1,2 $\lambda^{4}$3,5-oxathiadiazole 2-oxides in nonaqueous media
  作者：Nedime DÜRÜST、Yaşar DÜRÜST、Emine Özge GÖZLÜKAYA

  DOI：10.3906/kim-1303-46

  日期：——

  NH acidities of some 3-(p-substitutedphenyl)-1,2,4-oxadiazol-5(4H)-ones and 4-(p-substitutedphenyl)-1,2 \lambda^43,5-oxathiadiazole 2-oxides were determined in methanol by means of potentiometric titration with sodium methoxide. pK_a values of the title compounds calculated from the potentiometric data were interpreted on the basis of structural effects caused by para-substituted groups on the phenyl ring by plotting pK_a values versus Hammett \sigma_p^+ constants, which gave excellent linear correlations.

  一些3-(对取代苯基)-1,2,4-噁二唑-5(4H)-酮和4-(对取代苯基)-1,2λ^43,5-噻二氮杂烯-2-氧化物的NH酸度在甲醇中通过与甲氧化钠的电位滴定进行测定。根据电位数据计算出的标题化合物的pK_a值通过绘制pK_a值与Hammett σ_p^+常数的关系图来解释，这表明对取代基对苯环造成的结构效应，得到了很好的线性相关性。
• Tertiary Amines as Temporary Masked Secondary Amines: A Direct Access to 5-Dialkylamino-1,2,4-oxadiazoles from 1,2,4-Oxadiazol-5(4H)-ones
  作者：Wong Phakhodee、Muh Alfliadhi、Mookda Pattarawarapan、Surat Hongsibsong、Nittaya Wiriya

  DOI：10.1055/s-0042-1751555

  日期：2024.5

  tertiary amines as temporary masked secondary amines to synthesize 5-dialkylamino 1,2,4-oxadiazoles via Ph3P-I2 mediated amination of 1,2,4-oxadiazol-5(4H)-ones was developed. A one-step N-dealkylative functionalization of tertiary amines with the 1,2,4-oxadiazole ring enables a convenient access to diverse 5-amino-1,2,4-oxadiazoles. Additionally, orthogonally functionalized piperazine derivatives can be