N-methyl-N-succinimidomethylacetamide | 87329-73-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-methyl-N-succinimidomethylacetamide
• 英文别名: N-[(2,5-dioxo-1-pyrrolidinyl)methyl]-N-methylacetamide；N-methyl-N-succinimidomethylacetoamide；N-[(2,5-dioxopyrrolidin-1-yl)methyl]-N-methylacetamide
• CAS: 87329-73-5
• 化学式: C₈H₁₂N₂O₃
• 分子量: 184.195
• InChiKey: JAMDFKVRHZENDW-UHFFFAOYSA-N

物化性质

• 沸点：
  397.7±25.0 °C(Predicted)
• 密度：
  1.246±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-溴代丁二酰亚胺(NBS) 、 N,N-二甲基乙酰胺 在 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 以70%的产率得到N-methyl-N-succinimidomethylacetamide
  参考文献：
  名称：

  Caristi, Corrado; Ferlazzo, Alida; Gattuso, Mario, Journal of the Chemical Society. Perkin transactions I, 1984, # 2, p. 281 - 285

  摘要：

  DOI：

文献信息

• Unusual behaviour of N-bromosuccinimide. Conversion of N,N-dimethylamides to N-methyl,N-succinimidomethylamides
  作者：C. Caristi、G. Cimino、A. Ferlazzo、M. Gattuso、M. Parisi

  DOI：10.1016/s0040-4039(00)87977-0

  日期：1983.1

  N,N-Dimethylamides are converted by NBS to the N-succinimidomethylamides in an almost quantitative yield. The intermediacy of bromomethylderivatives which further react with NBS to give is demonstrated.

  N，N-二甲基酰胺被NBS以几乎定量的产率转化为N-琥珀酰亚胺基甲基酰胺。证明了溴甲基衍生物进一步与NBS反应生成中间体。
• KI-catalyzed imidation of sp3 C–H bond adjacent to amide nitrogen atom
  作者：Zhi-Qi Lao、Wen-He Zhong、Qing-Hua Lou、Zhong-Jun Li、Xiang-Bao Meng

  DOI：10.1039/c2ob26430g

  日期：——

  We have developed a new KI-catalyzed method for the imidation of an sp3 C–H bond adjacent to an amide nitrogen atom by using TBHP (tert-butyl hydroperoxide, 70% aqueous solution) as the oxidant. This novel procedure tolerated air and moisture and provided a series of novel products in moderate to excellent yields under mild conditions.

  我们开发了一种新的KI催化方法，用于在amide氮原子邻近的sp3 C–H键上进行亚胺化，采用TBHP（过氧化叔丁酯，70%水溶液）作为氧化剂。这一新方法能够耐受空气和湿气，并在温和条件下提供了一系列新的产品，产率从中等到优异。
• Incompatibilities between <i>N</i>-Bromosuccinimide and Solvents
  作者：Sumio Shimizu、Yoshiaki Imamura、Tatsuo Ueki

  DOI：10.1021/op400360k

  日期：2014.2.21

  Incompatibilities between N-bromosuccinimide (NBS) and solvents were examined by measuring the heat of reaction by an advanced reactive system screening tool (ARSST) and a reaction calorimeter (RC1e). The ARSST experiments showed that amides, THF, and toluene solutions require consideration of incompatibilities with NBS. Isothermal analyses by RC1e revealed accurate heats of incompatibilities and the autocatalytic behaviors of the incompatibilities. Experiments in the presence of a radical initiator or inhibitor demonstrated that the incompatibility is caused by the radical mechanism and the incompatibility is increased by the presence of radical initiators. Further experiments made clear that DBDMH, an alternative brominating reagent, showed behavior similar to that of NBS.
• CARISTI, C.;CIMINO, G.;FERLAZZO, A.;GATTUSO, M.;PARISI, M., TETRAHEDRON LETT., 1983, 24, N 26, 2685-2688
  作者：CARISTI, C.、CIMINO, G.、FERLAZZO, A.、GATTUSO, M.、PARISI, M.

  DOI：——

  日期：——
• CARISTI, C.;FERLAZZO, A.;GATTUSO, M., J. CHEM. SOC. PERKIN TRANS., 1984, N 2, 281-285
  作者：CARISTI, C.、FERLAZZO, A.、GATTUSO, M.

  DOI：——

  日期：——