3-(2,4-Dichlorophenyl)-1,2,3-oxadiazol-3-ium-5-olate | 91982-87-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(2,4-Dichlorophenyl)-1,2,3-oxadiazol-3-ium-5-olate
• 英文别名: 3-(2,4-dichlorophenyl)oxadiazol-3-ium-5-olate
• CAS: 91982-87-5
• 化学式: C₈H₄Cl₂N₂O₂
• 分子量: 231.038
• InChiKey: DFDPWIYOIPDGDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2,4-Dichlorophenyl)-1,2,3-oxadiazol-3-ium-5-olate 在 1,3-二溴-5,5-二甲基海因 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.7h， 以95%的产率得到
  参考文献：
  名称：

  Catalytic Activity of 1,3-Dibromo-5,5-dimethylhydantoin (DBH) in the One-Pot Transformation ofN-Arylglycines toN-Arylsydnones in the Presence of NaNO₂/Ac₂O under Neutral Conditions: Subsequent Bromination of these Sydnones to their 4-Bromo Derivatives

  摘要：

  研究发现，在温和的中性条件下，1,3-二溴-5,5-二甲基海因（DBH）可与 NaNO2 和 Ac2O 结合，高效催化各种 N-芳基甘氨酸通过 N-亚硝基化和环化反应一锅转化为茚酮类化合物，收率高达 80-94%。此外，研究还表明，DBH 可以方便地促进这些茚酮在室温下于 DMF 中溴化成其 4-溴取代的同系物，收率极高。

  DOI：

  10.1055/s-2006-926380
• 作为产物：
  描述：

  2,4-二氯苯胺 在 1,3-二溴-5,5-二甲基海因 、 silica gel 、 高碘酸 、 sodium nitrite 作用下， 以 二氯甲烷 为溶剂， 反应 6.39h， 生成 3-(2,4-Dichlorophenyl)-1,2,3-oxadiazol-3-ium-5-olate
  参考文献：
  名称：

  Microwave-assisted Synthesis of N-Arylglycines: Improvement of Sydnone Synthesis

  摘要：

  Reactions of anilines with ethyl bromoacetate under microwave irradiation have afforded N-arylglycines that are subsequently converted to their N-nitroso derivatives with a combination of silica chloride or periodic acid, wet SiO2 and sodium nitrite in CH2Cl2 with satisfactory yields. In the final step, the use of 1,3-dibromo-5,5-dimethylhydantoin (DBH) as a new and effective reagent for dehydration of N-nitroso-N-arylglycines to sydnones was successfully examined.

  DOI：

  10.3987/com-05-10574

文献信息

• One-Pot Conversion of N-Arylglycines to Sydnones Efficiently Promoted by Bis-chlorine-1,4-diazabicyclo[2.2.2]octane Complex (Cl2-DABCO) in the Presence of NaNO2/Ac2O under Neutral Conditions
  作者：Davood Azarifar、Hassan Ghasemnejad-Bosra、Mahmood Tajbaksh、Setareh Habibzadeh

  DOI：10.3987/com-07-11033

  日期：——

  Bis-chlorine-1,4-diazabicyclo[2.2.2]octane complex, (Cl 2 -DABCO), has been found as an active chlorine complex for effective one-pot conversion of various N-arylglycines to sydnones in high yields (85-95%) under mild and neutral condition.

  Bis-chlorine-1,4-diazabicyclo[2.2.2]octane complex, (Cl 2 -DABCO) 被发现是一种活性氯络合物，可有效地将各种 N-芳基甘氨酸一锅法转化为高收率 (85 -95%) 在温和和中性条件下。
• N,N,N’,N’-Tetrabromobenzene-1,3-disolfonamide (TBBDS) as an Efficient Promoter for One-Pot Conversion of N-Arylglycines to Sydnones in the Presence of NaNO2/Ac2O under Neutral Conditions
  作者：Davood Azarifar、Mahmood Tajbaksh、Hassan Ghasemnejad-Bosra、Ramin Ghorbani-Vaghei

  DOI：10.3987/com-06-10859

  日期：——

  N,N,N',N'-Tetrabromobenzene-1,3-disolfonamide (TBBDS)-promoted one-pot conversion of various N-arylglycines to sydnones using a combination of NaNO 2 and Ac 2 O has been achieved efficiently through N-nitrosation followed by cyclization in high yields (85-95%) under mild and neutral conditions.

  N,N,N',N'-四溴苯-1,3-二磺酰胺 (TBBDS) - 使用 NaNO 2 和 Ac 2 O 的组合促进了各种 N-芳基甘氨酸到 sydnones 的一锅转化，通过 N-亚硝化，然后在温和和中性条件下以高产率 (85-95%) 环化。
• N-Bromosuccinimide (NBS) as Promoter for Acylation of Sydnones in the Presence Acetic Anhydride under Neutral Conditions
  作者：Hassan Ghasemnejad-Bosra、Hassan Ghasemnejad-Bosra、Mina Haghdadi、Issa Gholampour-Azizi

  DOI：10.3987/com-07-11185

  日期：——

  Various 4 - acetyl sydnones (2) can be prepared by reaction of the corresponding 3-aryl sydnones (1) with acetic anhydride at ∼110 °C promoted by N-Bromosuccinimide (NBS) as an effective reagent for acylation of sydnones under neutral conditions in satisfactory yields.

  在 N-溴代琥珀酰亚胺 (NBS) 作为一种有效试剂在中性条件下酰化 sydones 的促进下，相应的 3-arylsydones (1) 与乙酸酐在 ∼110 °C 下反应，可以制备各种 4-乙酰 sydones (2)在令人满意的产量。
• 1,3-Dibromo-5,5-dimethylhydantoin (DBH) as an efficient promoter for acetylation of 3-arylsydnones in the presence of acetic anhydride under neutral conditions
  作者：Davood Azarifar、Hassan Ghasemnejad Bosra、Mahmood Tajbaksh

  DOI：10.1002/jhet.5570440231

  日期：2007.3

  1,3-Dibromo-5,5-dimethylhydantoin (DBH) has been found to efficiently promote the conversion of various 3-arylsydnones to their 4-acetyl congeners in the presence of acetic anhydride under neutral conditions in satisfactory yields.

  已经发现1，3-二溴-5，5-二甲基乙内酰脲（DBH）在乙酸酐存在下在中性条件下以令人满意的产率有效地促进了各种3-芳基sydnones向其4-乙酰基同源物的转化。
• Microwave-assisted Synthesis of N-Arylglycines: Improvement of Sydnone Synthesis
  作者：Davood Azarifar、Hassan Ghasemnejad Bosra、Mohammad-Ali Zolfigol、Mahmood Tajbaksh

  DOI：10.3987/com-05-10574

  日期：——

  Reactions of anilines with ethyl bromoacetate under microwave irradiation have afforded N-arylglycines that are subsequently converted to their N-nitroso derivatives with a combination of silica chloride or periodic acid, wet SiO2 and sodium nitrite in CH2Cl2 with satisfactory yields. In the final step, the use of 1,3-dibromo-5,5-dimethylhydantoin (DBH) as a new and effective reagent for dehydration of N-nitroso-N-arylglycines to sydnones was successfully examined.