N-(4-methoxy-benzyl)-N-methyl-glycine ethyl ester | 100619-26-9

• 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-(4-methoxy-benzyl)-N-methyl-glycine ethyl ester
• 英文别名: N-(4-Methoxy-benzyl)-N-methyl-glycin-aethylester；Ethyl 2-[(4-methoxyphenyl)methyl-methylamino]acetate
• CAS: 100619-26-9
• 化学式: C₁₃H₁₉NO₃
• mdl: MFCD13228758
• 分子量: 237.299
• InChiKey: YGWAMPIGYJZFPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-methoxy-benzyl)-N-methyl-glycine ethyl ester 在 一水合肼 作用下， 生成 N-(4-methoxy-benzyl)-N-methyl-glycine hydrazide
  参考文献：
  名称：

  Mndshojan et al., Izvestiya Akademii Nauk Armyanskoi SSR, Khimicheskie Nauki, 1958, vol. 11, p. 357,358

  摘要：

  DOI：
• 作为产物：
  描述：

  N-甲基-4-甲氧基苄胺 、 溴乙酸乙酯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 N-(4-methoxy-benzyl)-N-methyl-glycine ethyl ester
  参考文献：
  名称：

  Synthesis of Functionalized Fullerenes by Photoaddition of N-α-Trimethylsilyl-N-carboxymethyl-N-benzylamines to C60

  摘要：

  Photoaddition reactions of fullerene C-60 with N-alpha-trimethylsilyl-N-carboxymethyl-N-benzylamines, which contain various para-substituents, were explored in order to evaluate factors governing efficiencies of this potentially useful method for preparing functionalized fullerene derivatives. Observations made in this study show that two reaction pathways are followed in these photoreactions. The first involves initial formation of alpha-trimethylsilyl-aminium radicals and the C-60 anion radical by SET from the amines to the triplet excited state of C-60. This step is followed by desilylation to produce alpha-amino radicals. Coupling of these radicals with the anion radical of C-60 followed by protonation or with the hydrofullerene radical generated by protonation of the anion radical of C-60 then produces aminomethyl-1,2-dihydrofullerenes. When limited amounts of (3)o(2) are present in the reaction medium, fulleropyrrolidines are generated in low yields by a competitive pathway involving formation of singlet oxygen, which undergoes sequential H-atom abstractions from the N-alpha-trimethylsilyl-N-carboxymethyl-N-benzylamines to produce azomethine ylide intermediates. Dipolar cyloaddition of the ylides to C-60 then produces fulleropyrrolidines. Photoreactions of the C-60 and the amines in the presence of high (3)o(2) concentrations exclusively produce fulleropyrrolidine. In addition, the results show that photoreactions of non-silicon substituted, N-methyl-N-carboxymethyl-N-benzylamines with C-60 form fulleropyrrolidines independent of the concentration of O-3(2) present in the media.

  DOI：

  10.3987/com-15-s(t)19

文献信息

• Epoxide‐Mediated Stevens Rearrangements of α‐Amino‐Acid‐Derived Tertiary Allylic, Propargylic, and Benzylic Amines: Convenient Access to Polysubstituted Morpholin‐2‐ones
  作者：You‐Xiang Jin、Bang‐Kui Yu、Si‐Ping Qin、Shi‐Kai Tian

  DOI：10.1002/chem.201900635

  日期：2019.4.5

  A new strategy has been established for the synthesis of polysubstituted morpholin‐2‐ones through Stevens rearrangements of tertiary amines via in situ activation with epoxides. A range of α‐amino acid‐derived tertiary allylic, propargylic, and benzylic amines reacted with epoxides in the presence of zinc halide catalysts to afford structurally diverse allyl‐, allenyl‐, and benzyl‐substituted morpholin‐2‐ones

  已经建立了一种新的策略，该方法通过环氧化物的原位活化，通过叔胺的史蒂文斯重排来合成多取代的吗啉-2-酮。在卤化锌催化剂存在下，一系列α-氨基酸衍生的叔烯丙基，炔丙基和苄基胺与环氧化物反应，分别得到结构上不同的烯丙基，烯丙基和苄基取代的吗啉-2-酮。中等至良好的产量，具有较高的区域选择性。该过程涉及季铵盐内酯中间体的[2,3]-和[1,2] -Stevens重排，并且是通过串联形成C-N，C-O和C-N来制备多取代吗啉-2-酮的一种非常方便的方法。 C-C键。此外，用氮丙啶取代环氧化物可以合成多取代的哌嗪-2-酮。