methyl (2S)-2-[(2-bromophenyl)methylideneamino]propanoate | 218290-76-7

• 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: methyl (2S)-2-[(2-bromophenyl)methylideneamino]propanoate
• CAS: 218290-76-7
• 化学式: C₁₁H₁₂BrNO₂
• 分子量: 270.126
• InChiKey: GDEDPILXHWBNSJ-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[(2-bromophenyl)methylideneamino]propanoate 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 methyl (2S)-2-[(2-bromophenyl)methylamino]propanoate
  参考文献：
  名称：

  Application of Peptidyl Radicals into a New Radical Cascade Leading to Unsaturated γ-Lactams

  摘要：

  Radical cyclization of dipeptides 1a-h proceeds smoothly to give five- and seven-membered rings in good to moderate total yields using Stork's catalytic tin hydride method. A radical is generated on a protecting group and translocated to the peptide moiety. Following a cyclization reaction, the vinyl radical can abstract hydrogen from a benzyl group on an amine, which results in elimination of the protected amine group. Encouraging results have notably been obtained with amino acids other than glycine.

  DOI：

  10.1021/jo020602w
• 作为产物：
  描述：

  L-丙氨酸甲酯盐酸盐 、 邻溴苯甲醛 在 三乙胺 、 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 methyl (2S)-2-[(2-bromophenyl)methylideneamino]propanoate
  参考文献：
  名称：

  Application of Peptidyl Radicals into a New Radical Cascade Leading to Unsaturated γ-Lactams

  摘要：

  Radical cyclization of dipeptides 1a-h proceeds smoothly to give five- and seven-membered rings in good to moderate total yields using Stork's catalytic tin hydride method. A radical is generated on a protecting group and translocated to the peptide moiety. Following a cyclization reaction, the vinyl radical can abstract hydrogen from a benzyl group on an amine, which results in elimination of the protected amine group. Encouraging results have notably been obtained with amino acids other than glycine.

  DOI：

  10.1021/jo020602w

文献信息

• Synthesis of Optically Pure 2-Azetidinones Having <i>N</i>-Dehydroamino Acid Side-Chains
  作者：Benito Alcaide、Concepción Polanco、Miguel A. Sierra

  DOI：10.1055/s-1998-1667

  日期：1998.4

  An efficient, three step synthesis of optically pure N-vinyl-2-azetidinones 1 starting from α- or β-amino ester imines has been developed. Staudinger reaction between amino ester derived imines and ketene precursors gave 2-azetidinones 2. Enolate formation on the amino ester moiety of the optically pure 2-azetidinones 2, selenylation and, finally, MCPBA treatment afforded N-vinyl-2-azetidinones 1 in good to excellent yields, with total retention of the stereochemistry of the starting material. Compounds 2 bear the functionality needed to place a carboxy group contiguous to the lactam nitrogen, a structural feature common to all the active β-lactam antibiotics.

  从 δ- 或 δ²- 氨基酯亚胺开始，开发出了一种高效的三步合成光学纯 N-乙烯基-2-氮杂环丁酮 1 的方法。由氨基酯衍生的亚胺和烯酮前体发生施陶丁格反应，得到 2-氮杂环丁酮 2。在光学纯度较高的 2-氮杂环丁酮 2 的氨基酯分子上形成烯酸盐，然后进行硒化，最后经 MCPBA 处理，得到 N-乙烯基-2-氮杂环丁酮 1，收率从良好到极佳，并完全保留了起始原料的立体化学结构。化合物 2 具有将羧基与内酰胺氮相连所需的官能度，这是所有活性 δ-内酰胺类抗生素共有的结构特征。