甲基2-甲酰氨基-3-氧代丁酸酯 | 706822-01-7

• 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
• 中文名称: 甲基2-甲酰氨基-3-氧代丁酸酯
• 英文名称: N-(1-methoxycarbonyl-2-oxopropyl)formamide
• 英文别名: Methyl 2-formamido-3-oxobutanoate
• CAS: 706822-01-7
• 化学式: C₆H₉NO₄
• 分子量: 159.142
• InChiKey: QHHJOFJOTFMNOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲基2-甲酰氨基-3-氧代丁酸酯 在 碘 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以45%的产率得到5-甲基恶唑-4-甲酸甲酯
  参考文献：
  名称：

  N–H Insertion reactions of rhodium carbenoids. Part 5: A convenient route to 1,3-azoles

  摘要：

  Dirhodium(II) carboxylate catalysed reaction of diazocarbonyl compounds 2 in the presence of primary amides 1 results in the formation of alpha-acylaminoketones 3 (12 examples) by N-H insertion reaction of the intermediate rhodium carbene. The 1,4-dicarbonyl compounds 3 are readily converted into structurally diverse oxazoles 4 (11 examples) by cyclodehydration, thiazoles 5 (10 examples) by treatment with Lawesson's reagent, or imidazoles 6 (2 examples) by reaction with ammonia or methylamine. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.03.037
• 作为产物：
  描述：

  2-Diazo-3-oxo-butyric acid methyl ester 、 formamide 在 dirhodium tetraacetate 作用下， 以 1,2-二氯乙烷 为溶剂， 以43%的产率得到甲基2-甲酰氨基-3-氧代丁酸酯
  参考文献：
  名称：

  N–H Insertion reactions of rhodium carbenoids. Part 5: A convenient route to 1,3-azoles

  摘要：

  Dirhodium(II) carboxylate catalysed reaction of diazocarbonyl compounds 2 in the presence of primary amides 1 results in the formation of alpha-acylaminoketones 3 (12 examples) by N-H insertion reaction of the intermediate rhodium carbene. The 1,4-dicarbonyl compounds 3 are readily converted into structurally diverse oxazoles 4 (11 examples) by cyclodehydration, thiazoles 5 (10 examples) by treatment with Lawesson's reagent, or imidazoles 6 (2 examples) by reaction with ammonia or methylamine. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.03.037

文献信息

• N–H Insertion reactions of rhodium carbenoids. Part 5: A convenient route to 1,3-azoles
  作者：James R Davies、Peter D Kane、Christopher J Moody

  DOI：10.1016/j.tet.2004.03.037

  日期：2004.4

  Dirhodium(II) carboxylate catalysed reaction of diazocarbonyl compounds 2 in the presence of primary amides 1 results in the formation of alpha-acylaminoketones 3 (12 examples) by N-H insertion reaction of the intermediate rhodium carbene. The 1,4-dicarbonyl compounds 3 are readily converted into structurally diverse oxazoles 4 (11 examples) by cyclodehydration, thiazoles 5 (10 examples) by treatment with Lawesson's reagent, or imidazoles 6 (2 examples) by reaction with ammonia or methylamine. (C) 2004 Elsevier Ltd. All rights reserved.