(RS)-N-acetylalanine-N-methoxy-N-methylamide

• 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: (RS)-N-acetylalanine-N-methoxy-N-methylamide
• 英文别名: 2-acetamido-N-methoxy-N-methylpropanamide
• 化学式: C₇H₁₄N₂O₃
• mdl: MFCD18839889
• 分子量: 174.2
• InChiKey: RHVOGIHWWMMHOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.714
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (RS)-N-acetylalanine-N-methoxy-N-methylamide 在 Lindlar's catalyst 喹啉 、 氢气 、 lead acetate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 4.0h， 生成 trans-(RS)-2-acetamido-5-phenyl-4-penten-3-one
  参考文献：
  名称：

  Functionalized amido ketones: new anticonvulsant agents

  摘要：

  We have reported that functionalized amino acids (FAA) are potent anticonvulsants. Replacing the N-terminal amide group in FAA with phenethyl, styryl, and phenylethynyl units provided a series of functionalized amido ketones (FAK). We show that select FAK exhibit significant anticonvulsant activities thereby providing information about the structural requirements for FAA and FAK bioactivity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00434-6
• 作为产物：
  描述：

  N-乙酰-DL-丙氨酸 在 N-甲基吗啉 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.52h， 生成 (RS)-N-acetylalanine-N-methoxy-N-methylamide
  参考文献：
  名称：

  Functionalized amido ketones: new anticonvulsant agents

  摘要：

  We have reported that functionalized amino acids (FAA) are potent anticonvulsants. Replacing the N-terminal amide group in FAA with phenethyl, styryl, and phenylethynyl units provided a series of functionalized amido ketones (FAK). We show that select FAK exhibit significant anticonvulsant activities thereby providing information about the structural requirements for FAA and FAK bioactivity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00434-6

文献信息

• Tetramic acid and imidazolidinone syntheses via unexpected base induced cyclisations of alanine derived Weinreb amides
  作者：Colin L. Gibson、Alan R. Kennedy、Raghavendar R. Morthala、John A. Parkinson、Colin J. Suckling

  DOI：10.1016/j.tet.2008.05.058

  日期：2008.8

  base unexpectedly gave tetramic acid derivatives or an imidazolidinone. The tetramic acid derivatives were obtained by unusual cyclisation of N-acyl N-methoxy derivatives of alanine Weinreb amide upon treatment with potassium hexamethyldisilazide and benzyl bromide. In contrast, treatment of a bromobenzylidine alanine Weinreb amide with potassium hexamethyldisilazide gave rise to cyclisation to form

  丙氨酸的Weinreb酰胺的N-保护的衍生物与强碱的反应出乎意料地给出了四酸衍生物或咪唑啉酮。通过用六甲基二硅叠氮化钾和苄基溴处理，丙氨酸Weinreb酰胺的N-酰基N-甲氧基衍生物进行不寻常的环化反应，获得了四酸衍生物。相反，用六甲基二硅叠氮钾处理溴苄基丙氨酸丙氨酸Weinreb酰胺引起环化反应，形成咪唑啉酮。
• Functionalized amido ketones: new anticonvulsant agents
  作者：C BEGUIN

  DOI：10.1016/s0968-0896(03)00434-6

  日期：2003.9

  We have reported that functionalized amino acids (FAA) are potent anticonvulsants. Replacing the N-terminal amide group in FAA with phenethyl, styryl, and phenylethynyl units provided a series of functionalized amido ketones (FAK). We show that select FAK exhibit significant anticonvulsant activities thereby providing information about the structural requirements for FAA and FAK bioactivity. (C) 2003 Elsevier Ltd. All rights reserved.