3-ethynylphenylamino oxoacetate ethyl ester | 1178671-79-8

• 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: 3-ethynylphenylamino oxoacetate ethyl ester
• 英文别名: Ethyl [(3-ethynylphenyl)carbamoyl]formate；ethyl 2-(3-ethynylanilino)-2-oxoacetate
• CAS: 1178671-79-8
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: DTUATTALQFZXND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-ethynylphenylamino oxoacetate ethyl ester 、 N-1-苄基-3-甲基哌嗪 以 乙腈 为溶剂， 反应 6.0h， 生成 2-(4-benzyl-2-methylpiperazin-1-yl)-N-(3-ethynylphenyl)-2-oxoacetamide
  参考文献：
  名称：

  2,2,2-Trifluoroethyl Chlorooxoacetate—Universal Reagent for One-Pot Parallel Synthesis of N¹-Aryl-N²-alkyl-Substituted Oxamides

  摘要：

  A one-pot parallel synthesis of N-1-aryl-N-2-alkyl-substituted oxamides with 2,2,2-trifluoroethyl chlorooxoacetate was developed. The synthesis of a library of 45 oxamides revealed higher efficiency of this reagent over the known ethyl chlorooxoacetate. The reagent was successfully used to prepare the known oxamide-containing HIV entry inhibitors.

  DOI：

  10.1021/acscombsci.5b00091
• 作为产物：
  描述：

  3-氨基苯乙炔 、 草酰氯单乙酯 以 四氢呋喃 、 三乙胺 为溶剂， 反应 1.5h， 以97%的产率得到3-ethynylphenylamino oxoacetate ethyl ester
  参考文献：
  名称：

  新的单，双和三恶唑酮配体的合成与表征

  摘要：

  该通报介绍了带有多达三个N-苯基-草酰胺酸乙酯的新有机分子的合成和表征。合成是基于Sonogashira类型的交叉偶联反应与预先形成的草酰胺酸酯中间体构造单元进行的。短的合成途径很容易导致有价值的潜在草酰胺桥联配体，总的产率令人感兴趣。

  DOI：

  10.1016/j.tetlet.2010.07.117

文献信息

• Synthesis and characterization of new mono-, bis-, and tris-oxamato proligands
  作者：Christophe Stroh、Alexandrina Stuparu

  DOI：10.1016/j.tetlet.2010.07.117

  日期：2010.9

  This communication presents the synthesis and the characterization of new organic molecules bearing up to three N-phenyl-oxalamic acid ethyl esters. The syntheses are based on Sonogashira-type cross-coupling reactions with preformed oxalamic ester intermediate building blocks. The short synthetic pathways lead easily to valuable potential oxamato-bridging ligands with overall interesting yields.

  该通报介绍了带有多达三个N-苯基-草酰胺酸乙酯的新有机分子的合成和表征。合成是基于Sonogashira类型的交叉偶联反应与预先形成的草酰胺酸酯中间体构造单元进行的。短的合成途径很容易导致有价值的潜在草酰胺桥联配体，总的产率令人感兴趣。
• 2,2,2-Trifluoroethyl Chlorooxoacetate—Universal Reagent for One-Pot Parallel Synthesis of <i>N</i>¹-Aryl-<i>N</i>²-alkyl-Substituted Oxamides
  作者：Andrey V. Bogolubsky、Yurii S. Moroz、Pavel K. Mykhailiuk、Sergey E. Pipko、Anton V. Zhemera、Anzhelika I. Konovets、Olena O. Stepaniuk、Inna S. Myronchuk、Yurii V. Dmytriv、Roman A. Doroschuk、Olga A. Zaporozhets、Andrey Tolmachev

  DOI：10.1021/acscombsci.5b00091

  日期：2015.10.12

  A one-pot parallel synthesis of N-1-aryl-N-2-alkyl-substituted oxamides with 2,2,2-trifluoroethyl chlorooxoacetate was developed. The synthesis of a library of 45 oxamides revealed higher efficiency of this reagent over the known ethyl chlorooxoacetate. The reagent was successfully used to prepare the known oxamide-containing HIV entry inhibitors.