2-Oxo-hexanoic acid methylamide | 141694-34-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-Oxo-hexanoic acid methylamide
• 英文别名: N-methyl-2-oxohexanamide
• CAS: 141694-34-0
• 化学式: C₇H₁₃NO₂
• mdl: MFCD19220103
• 分子量: 143.186
• InChiKey: VEHYHQATIGTVKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.714
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N,N'-二甲氧基-N,N'-二甲基乙二酰二胺 、 alkaline earth salt of/the/ methylsulfuric acid 以 四氢呋喃 为溶剂， 以52%的产率得到N-Methoxy-N-methyl-α-oxohexaneamide
  参考文献：
  名称：

  .alpha.-Keto Amides and 1,2-Diketones from N,N'-Dimethoxy-N,N'-dimethylethanediamide. A Synthetic and Mechanistic Investigation

  摘要：

  N,N'-Dimethoxy-N,N'-dimethylethanediamide (1), a 1,2-dicarbonyl synthon prepared from oxalyl chloride, undergoes nucleophilic displacements with Grignard reagents to provide alpha-keto amides 2-12 in 28-90% yields. The synthon also undergoes double nucleophilic displacements with organolithium reagents to furnish symmetrical 1,2-diketones 15-23 in 15-84% yields. A mechanism accounting for all the products from the reaction of 1 with nucleophiles has been proposed. Several control experiments were carried out to support the proposed mechanism.

  DOI：

  10.1021/jo00121a021

文献信息

• N,N′-Dimethoxy-N,Nt́-Dimethylethanediamide: A Useful α-Oxo-N-Methoxy-N-Methylamide and 1,2-Diketone Synthon
  作者：Mukund P. Sibi、Rajiv Sharma、Kevin L. Paulson

  DOI：10.1016/0040-4039(92)88108-h

  日期：1992.4

  N,N'-Dimethoxy-N,N'-dimethylethanediamide on treatment with one to two equivalents of alkyl, aryl, and benzyl Grignard reagents provide alpha-oxo-N-methoxy-N-methylamides in good to excellent yields and on reaction with excess aryllithiums furnish moderate to good yields of symmetrical 1,2-diarylketones.
• .alpha.-Keto Amides and 1,2-Diketones from N,N'-Dimethoxy-N,N'-dimethylethanediamide. A Synthetic and Mechanistic Investigation
  作者：Mukund P. Sibi、Mali Marvin、Rajiv Sharma

  DOI：10.1021/jo00121a021

  日期：1995.8

  N,N'-Dimethoxy-N,N'-dimethylethanediamide (1), a 1,2-dicarbonyl synthon prepared from oxalyl chloride, undergoes nucleophilic displacements with Grignard reagents to provide alpha-keto amides 2-12 in 28-90% yields. The synthon also undergoes double nucleophilic displacements with organolithium reagents to furnish symmetrical 1,2-diketones 15-23 in 15-84% yields. A mechanism accounting for all the products from the reaction of 1 with nucleophiles has been proposed. Several control experiments were carried out to support the proposed mechanism.