(S)-methyl 3-(Boc-amino)-4-(methoxy(methyl)amino)-4-oxobutanoate | 641637-34-5

• 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: (S)-methyl 3-(Boc-amino)-4-(methoxy(methyl)amino)-4-oxobutanoate
• 英文别名: methyl (3S)-4-[methoxy(methyl)amino]-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoate
• CAS: 641637-34-5
• 化学式: C₁₂H₂₂N₂O₆
• 分子量: 290.316
• InChiKey: OEQBXTXSHPBUQY-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-methyl 3-(Boc-amino)-4-(methoxy(methyl)amino)-4-oxobutanoate 在 盐酸 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 73.0h， 生成 methyl (3S)-5-methyl-3-(2-methylprop-2-enoylamino)-4-oxohex-5-enoate
  参考文献：
  名称：

  Improving the Strategy and Performance of Molecularly Imprinted Polymers Using Cross-Linking Functional Monomers

  摘要：

  A new strategy for monomer design has been investigated that combines interactive monomer functionality with a cross-linking format, giving as a result noncovalent molecularly imprinted polymers (MIPS) with improved performance. This strategy was explored under the premise that more functionality could be introduced without suffering performance losses due to reduced cross-linking. While this proved to be correct, equally important contributions to selectivity enhancement at the molecular level by conformation control and diastereomeric complexation were also discovered. Monomers derived from L-serine and L-aspartic acid were synthesized and used to prepare MIPs, with the best performance obtained for the MIP formulated with the serine-based cross-linker (N,O-bis-methacryloyl L-serine, 3), versus the aspartic-acid-based cross-linkers and the traditional methacrylic acid/ethylene glycol dimethacrylate (MAA/EGDMA) formulation. Quantitative structure-selectivity relationship (QSSR) studies revealed that the improved performance of 3 was due to three key factors: (1) the cross-linking nature of this monomer; (2) control of conformational flexibility; (3) a strong influence of monomer chirality on enantioselectivity in MIPS.

  DOI：

  10.1021/jo0352225
• 作为产物：
  描述：

  二甲羟胺盐酸盐 、 Boc-L-天冬氨酸 4-甲酯 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到(S)-methyl 3-(Boc-amino)-4-(methoxy(methyl)amino)-4-oxobutanoate
  参考文献：
  名称：

  通过天冬氨酸等价物的格氏反应合成手性 β-氨基酸衍生物

  摘要：

  通过 2,4,5-三氟苯基溴化镁与 L-天冬氨酸的 Weinreb 酰胺衍生物的格利雅反应，开发了一种手性 β-氨基酸衍生物的新合成路线。天冬氨酸等价物由L-天冬氨酸分四步合成，格氏试剂通过Br-Mg-交换反应制备。在格氏反应和随后的还原之后获得目标化合物。L-天冬氨酸很好地保留了手性胺的立体结构。

  DOI：

  10.3184/030823410x12843925746143

文献信息

• The Synthesis of a Chiral β-Amino Acid Derivative by the Grignard Reaction of an Aspartic Acid Equivalent
  作者：Feng Liu、Wansheng Yu、Wenhua Ou、Xiaojiong Xu、Libo Ruan、Xiaoke Wang、Yiming Li、Xijiang Peng、Xiaohu Tao、Jun Mao、Jiaomei Wan、Xianhua Pan

  DOI：10.3184/030823410x12843925746143

  日期：2010.10

  to chiral β-amino acid derivative has been developed by a Grignard reaction of 2,4,5-trifluo-rophenyl magnesium bromide with the Weinreb amide derivative of L-aspartic acid. The aspartic equivalent was synthesised from L-aspartic acid in four steps, and the Grignard reagent was prepared by Br–Mg-exchange reaction. The target compound was achieved after the Grignard reaction and a subsequent reduction

  通过 2,4,5-三氟苯基溴化镁与 L-天冬氨酸的 Weinreb 酰胺衍生物的格利雅反应，开发了一种手性 β-氨基酸衍生物的新合成路线。天冬氨酸等价物由L-天冬氨酸分四步合成，格氏试剂通过Br-Mg-交换反应制备。在格氏反应和随后的还原之后获得目标化合物。L-天冬氨酸很好地保留了手性胺的立体结构。
• Improving the Strategy and Performance of Molecularly Imprinted Polymers Using Cross-Linking Functional Monomers
  作者：Martha Sibrian-Vazquez、David A. Spivak

  DOI：10.1021/jo0352225

  日期：2003.12.1

  A new strategy for monomer design has been investigated that combines interactive monomer functionality with a cross-linking format, giving as a result noncovalent molecularly imprinted polymers (MIPS) with improved performance. This strategy was explored under the premise that more functionality could be introduced without suffering performance losses due to reduced cross-linking. While this proved to be correct, equally important contributions to selectivity enhancement at the molecular level by conformation control and diastereomeric complexation were also discovered. Monomers derived from L-serine and L-aspartic acid were synthesized and used to prepare MIPs, with the best performance obtained for the MIP formulated with the serine-based cross-linker (N,O-bis-methacryloyl L-serine, 3), versus the aspartic-acid-based cross-linkers and the traditional methacrylic acid/ethylene glycol dimethacrylate (MAA/EGDMA) formulation. Quantitative structure-selectivity relationship (QSSR) studies revealed that the improved performance of 3 was due to three key factors: (1) the cross-linking nature of this monomer; (2) control of conformational flexibility; (3) a strong influence of monomer chirality on enantioselectivity in MIPS.