N-(2-Methylsulfanyl-phenyl)-oxalamic acid ethyl ester | 69066-10-0

• 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
• 英文名称: N-(2-Methylsulfanyl-phenyl)-oxalamic acid ethyl ester
• 英文别名: Ethyl 2-((2-(methylthio)phenyl)amino)-2-oxoacetate；ethyl 2-(2-methylsulfanylanilino)-2-oxoacetate
• CAS: 69066-10-0
• 化学式: C₁₁H₁₃NO₃S
• 分子量: 239.295
• InChiKey: GUXJCTHPKIYIJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-Methylsulfanyl-phenyl)-oxalamic acid ethyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (S)-3-Methyl-2-[2-(2-methylsulfanyl-phenylamino)-ethylamino]-butan-1-ol
  参考文献：
  名称：

  Design and synthesis of new bidentate alkoxy-NHC ligands for enantioselective copper-catalyzed conjugate addition

  摘要：

  A new family of chiral alkoxy-N-heterocyclic carbene (NHC) ligands has been designed for the enantioselective copper-catalyzed conjugate addition of dialkylzincs to enones. These new bidentate NHC ligands were synthesized in high overall yields using a five-step procedure starting from commercially available beta-aminoalcohols. Influence of the temperature, base, solvent and copper source were studied in order to optimize the stereoselectivity of the addition. High reactivity and excellent enantioselectivity were obtained at ambient temperature with a range of cyclic enones and dialkylzinc. Addition to acyclic enones has also been studied. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.04.027
• 作为产物：
  描述：

  2-氨基茴香硫醚 、 草酰氯单乙酯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 N-(2-Methylsulfanyl-phenyl)-oxalamic acid ethyl ester
  参考文献：
  名称：

  Design and synthesis of new bidentate alkoxy-NHC ligands for enantioselective copper-catalyzed conjugate addition

  摘要：

  A new family of chiral alkoxy-N-heterocyclic carbene (NHC) ligands has been designed for the enantioselective copper-catalyzed conjugate addition of dialkylzincs to enones. These new bidentate NHC ligands were synthesized in high overall yields using a five-step procedure starting from commercially available beta-aminoalcohols. Influence of the temperature, base, solvent and copper source were studied in order to optimize the stereoselectivity of the addition. High reactivity and excellent enantioselectivity were obtained at ambient temperature with a range of cyclic enones and dialkylzinc. Addition to acyclic enones has also been studied. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.04.027

文献信息

• Design and synthesis of new bidentate alkoxy-NHC ligands for enantioselective copper-catalyzed conjugate addition
  作者：Hervé Clavier、Ludovic Coutable、Loïc Toupet、Jean-Claude Guillemin、Marc Mauduit

  DOI：10.1016/j.jorganchem.2005.04.027

  日期：2005.11

  A new family of chiral alkoxy-N-heterocyclic carbene (NHC) ligands has been designed for the enantioselective copper-catalyzed conjugate addition of dialkylzincs to enones. These new bidentate NHC ligands were synthesized in high overall yields using a five-step procedure starting from commercially available beta-aminoalcohols. Influence of the temperature, base, solvent and copper source were studied in order to optimize the stereoselectivity of the addition. High reactivity and excellent enantioselectivity were obtained at ambient temperature with a range of cyclic enones and dialkylzinc. Addition to acyclic enones has also been studied. (c) 2005 Elsevier B.V. All rights reserved.