C-(2-nitrophenyl)-N-benzyl-nitrone | 919112-39-3

• 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: C-(2-nitrophenyl)-N-benzyl-nitrone
• 英文别名: N-benzyl-1-(2-nitrophenyl)methanimine oxide
• CAS: 919112-39-3
• 化学式: C₁₄H₁₂N₂O₃
• 分子量: 256.261
• InChiKey: RPSUEFQITRFHQA-PTNGSMBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  74.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  C-(2-nitrophenyl)-N-benzyl-nitrone 在 盐酸羟胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 16.0h， 生成 N-Benzylidenebenzylamine N-oxide
  参考文献：
  名称：

  One‐Pot Synthesis and Hydroxylaminolysis of Asymmetrical Acyclic Nitrones

  摘要：

  Aromatic aldehydes 1 were reductively aminated to the corresponding secondary amines 2 using NaBH4 in methanol in good yields. Amines 2 were oxidized with H2O2-WO42- regioselectively to nitrones 3, the structures of which were easily determined by reacting them with hydroxylamine hydrochloride as well as by spectral means. The products of hydroxylaminolysis in ether proved to be the corresponding benzaldehyde oximes 4 and benzyl or methyl hydroxylamine hydrochlorides 5.

  DOI：

  10.1080/00397910500191169
• 作为产物：
  描述：

  N-Benzylidenebenzylamine N-oxide 在 盐酸羟胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 8.0h， 生成 C-(2-nitrophenyl)-N-benzyl-nitrone
  参考文献：
  名称：

  One‐Pot Synthesis and Hydroxylaminolysis of Asymmetrical Acyclic Nitrones

  摘要：

  Aromatic aldehydes 1 were reductively aminated to the corresponding secondary amines 2 using NaBH4 in methanol in good yields. Amines 2 were oxidized with H2O2-WO42- regioselectively to nitrones 3, the structures of which were easily determined by reacting them with hydroxylamine hydrochloride as well as by spectral means. The products of hydroxylaminolysis in ether proved to be the corresponding benzaldehyde oximes 4 and benzyl or methyl hydroxylamine hydrochlorides 5.

  DOI：

  10.1080/00397910500191169

文献信息

• Cycloaddition of Acyclic Nitrones with Phenyl Isocyanate: Synthesis and Ring‐Opening Reactions of 1,2,4‐Oxadiazolidin‐5‐ones
  作者：Necdet Coşkun、Aydın Parlar

  DOI：10.1080/00397910500501466

  日期：2006.5

  unsubstituted or electron‐donating substituents on the C‐phenyl 1a,c,f with phenyl isocyanate proceeds smoothly for a short time with high yields to give the corresponding 1,2,4‐oxadiazolidinone 2, and 1b,d,e with electron‐withdrawing substituents gave the corresponding oxadiazolidinone in moderate yields after prolonged heating. Oxadiazolidinones 2a,c,f undergo diethylamine‐induced fragmentation for a short

  摘要 C-苯基 1a,c,f 上带有未取代或给电子取代基的硝酮与异氰酸苯酯在短时间内顺利进行环加成反应，得到相应的 1,2,4-恶二唑烷酮 2 和 1b，带有吸电子取代基的 d,e 在长时间加热后以中等产率得到相应的恶二唑烷酮。恶二唑烷酮 2a,c,f 会在短时间内经历二乙胺诱导的碎裂，得到相应的席夫碱，而恶二唑烷酮 2b,d,e 在这些条件下保持不变。在二乙胺存在下长时间加热 2d,e 导致复杂的混合物。在 2b 的情况下，相应的脒是反应的主要产物。
• Synthesis and new rearrangements of 4-isoxazolin-4,5-dicarboxylic acid derivatives
  作者：Necdet Coşkun、Aylin Öztürk

  DOI：10.1016/j.tet.2006.09.074

  日期：2006.12

  Acyclic nitrones react with dimethyl acetylenedicarboxylate (DMAD) to give stable isoxazolines, from which the ones that contain electron-donating aromatic rings at the C3 position (R1) were shown to undergo unprecedented fragmentation at room temperature, giving the R1-aldehyde and inseparable product mixtures, probably due to the formation of highly reactive species such as iminocarbenes. Attempts

  无环硝酮与乙炔二甲酸二甲酯（DMAD）反应生成稳定的异恶唑啉，据显示，异恶唑啉在C3位置（R 1）含给电子性芳环的那些在室温下经历了空前的断裂，得到R 1醛和不可分离的产物混合物，可能是由于形成了高反应性的物质，如亚氨基卡宾。试图通过在甲苯中回流将异恶唑啉转化为相应的稳定的甲亚胺基亚胺，再次导致与上述相同的产物混合物（例如，室温分解）。当异恶唑啉在室温下与甲醇反应时，可提供高度官能化的非对映异构体混合物。同样，当异恶唑啉与丙胺反应时，可以区域选择性地产生相应的酰胺，所有这些酰胺都比母体异恶唑啉更稳定。