C-(2-nitrophenyl)-N-methyl-nitrone | 41106-02-9

• 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-methyl-nitrone
• 英文别名: α-(o-Nitrophenyl)-N-methyl-nitron；N-methyl-1-(2-nitrophenyl)methanimine oxide
• CAS: 41106-02-9
• 化学式: C₈H₈N₂O₃
• 分子量: 180.163
• InChiKey: OGMOYZKACAZVKU-TWGQIWQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 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-methyl-nitrone 在 盐酸羟胺 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 4.0h， 以98%的产率得到N-甲基羟胺盐酸盐
  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-甲基-2-硝基苄胺 在 sodium tungstate 、 双氧水 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 C-(2-nitrophenyl)-N-methyl-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。
• Crystallographic and conformational analysis of 2-methyl-3-(2-nitro-phenyl)-4-phenyl-[1,2,4]oxadiazolidin-5-one
  作者：Hasan Karabıyık、Muhittin Aygün、Necdet Coşkun、Canan Kazak

  DOI：10.1007/s10870-005-2859-3

  日期：2005.1

  Molecular and crystal structure of 2-methyl-3-(2-nitro-phenyl)-4-phenyl-[1,2,4]oxadiazolidin-5-one, C15H13N3O4, have been determined by single crystal X-ray diffraction study. The title compound is monoclinic, with a = 10.0313(8) Å, b = 9.0372(5) Å, c = 15.5964(14) Å, β = 96.926(7)∘, Z = 4, D x = 1.42 g/cm3, μ (Mo-Kα) = 0.105 mm−1, and space group is P 21/c. The structure was solved by direct methods and refined to a final R = 0.036 for 1894 reflections with I > 4σ (I). The crystal structure is stabilized by C–H⋅sO type inter-molecular, C–H⋅sN and C–H⋅sO type intra-molecular, π–π stacking and edge to face (C–H⋅s π-ring) interactions. To enlighten conformational flexibility of the title molecule, selected two torsion angles are varied from −180∘ to +180∘ in every 10∘ separetely and then molecular energy profile is calculated and construed.

  通过单晶 X 射线衍射研究确定了 2-甲基-3-(2-硝基苯基)-4-苯基-[1,2,4]恶二唑烷-5-酮 C15H13N3O4 的分子和晶体结构。标题化合物为单斜晶系，a = 10.0313(8) Å, b = 9.0372(5) Å, c = 15.5964(14) Å, β = 96.926(7)∘, Z = 4, D x = 1.42 g/cm3, μ (Mo-Kα) = 0.105 mm-1, 空间群为 P 21/c。该结构通过直接方法求解，并在 1894 次反射中精炼出最终 R = 0.036，I > 4σ (I)。该晶体结构通过 C-H⋅sO 型分子间相互作用、C-H⋅sN 和 C-H⋅sO 型分子内相互作用、π-π 堆积和边到面（C-H⋅s π-环）相互作用而得到稳定。为了揭示标题分子的构象灵活性，所选的两个扭转角从 -180∘ 到 +180∘ 每隔 10∘ 变化一次，然后计算和解释分子能谱。