甲基2-[(甲氧羰基)氨基]-3-氧代丁酸酯 | 952029-14-0

• 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-[(甲氧羰基)氨基]-3-氧代丁酸酯
• 英文名称: Methyl 2-[(methoxycarbonyl)amino]-3-oxobutanoate
• 英文别名: methyl 2-(methoxycarbonylamino)-3-oxobutanoate
• CAS: 952029-14-0
• 化学式: C₇H₁₁NO₅
• 分子量: 189.168
• InChiKey: HKUMKVZZFVXTBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲基2-[(甲氧羰基)氨基]-3-氧代丁酸酯 在 bis(η3-allyl-μ-chloropalladium(II)) 、 potassium chloride 苯磺酰胺 、 potassium acetate 、 L-Selectride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 29.0h， 生成 methyl (R,E)-2-((S)-1-hydroxyethyl)-2-((methoxycarbonyl)amino)-5-phenylpent-4-enoate
  参考文献：
  名称：

  Pd-catalyzed enantioselective synthesis of quaternary α-amino acid derivatives using a phenylalanine-derived P-chirogenic diaminophosphine oxide

  摘要：

  A Pd-catalyzed enantio selective synthesis of quaternary alpha-amino acid derivatives using a phenylalanine-derived P-chirogenic diaminophosphine oxide is described. Asymmetric allylic substitution using acyclic beta-keto esters with a nitrogen functional group at the alpha-carbon as prochiral nucleophiles proceeded in the presence of 5 mol % of Pd catalyst, 10 mol % of chiral diaminophosphine oxide 1j, BSA, and appropriate additives, affording the corresponding quaternary alpha-amino acid derivatives in excellent yield and in up to 92% ee. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.020
• 作为产物：
  描述：

  Methyl 2-((tert-butoxycarbonyl)amino)-3-oxobutanoate 在 盐酸 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 生成 甲基2-[(甲氧羰基)氨基]-3-氧代丁酸酯
  参考文献：
  名称：

  Pd-catalyzed enantioselective synthesis of quaternary α-amino acid derivatives using a phenylalanine-derived P-chirogenic diaminophosphine oxide

  摘要：

  A Pd-catalyzed enantio selective synthesis of quaternary alpha-amino acid derivatives using a phenylalanine-derived P-chirogenic diaminophosphine oxide is described. Asymmetric allylic substitution using acyclic beta-keto esters with a nitrogen functional group at the alpha-carbon as prochiral nucleophiles proceeded in the presence of 5 mol % of Pd catalyst, 10 mol % of chiral diaminophosphine oxide 1j, BSA, and appropriate additives, affording the corresponding quaternary alpha-amino acid derivatives in excellent yield and in up to 92% ee. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.020

文献信息

• Pd-catalyzed enantioselective synthesis of quaternary α-amino acid derivatives using a phenylalanine-derived P-chirogenic diaminophosphine oxide
  作者：Tetsuhiro Nemoto、Teisuke Harada、Takayoshi Matsumoto、Yasumasa Hamada

  DOI：10.1016/j.tetlet.2007.07.020

  日期：2007.9

  A Pd-catalyzed enantio selective synthesis of quaternary alpha-amino acid derivatives using a phenylalanine-derived P-chirogenic diaminophosphine oxide is described. Asymmetric allylic substitution using acyclic beta-keto esters with a nitrogen functional group at the alpha-carbon as prochiral nucleophiles proceeded in the presence of 5 mol % of Pd catalyst, 10 mol % of chiral diaminophosphine oxide 1j, BSA, and appropriate additives, affording the corresponding quaternary alpha-amino acid derivatives in excellent yield and in up to 92% ee. (c) 2007 Elsevier Ltd. All rights reserved.