ethyl α-nitro-β-(phenylthio)acrylate | 73387-20-9

• 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: ethyl α-nitro-β-(phenylthio)acrylate
• 英文别名: ethyl (E)-2-nitro-3-phenylsulfanylprop-2-enoate
• CAS: 73387-20-9
• 化学式: C₁₁H₁₁NO₄S
• 分子量: 253.279
• InChiKey: GLIPLLWNPXUZKD-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl α-nitro-β-(phenylthio)acrylate 以 氯仿 为溶剂， 反应 48.0h， 生成 2(Z)-ethyl β-sulfanyl-α-nitroacrylate
  参考文献：
  名称：

  Sulfanyl-methylene-5(4H)-oxazolones and β-sulfanyl-α-nitroacrylates as appealing dienophiles for the synthesis of conformationally constrained cysteine analogues

  摘要：

  A new class of masked constrained cysteine derivatives containing the norbornen/ane scaffold were prepared by the way of Diets-Alder cycloaddition reaction by exploitation of two different dienophiles, sulfanyl-methylene-5(4H)-oxazolones and beta-sulfanyl-alpha-nitroacrylates. The new norbornen/ane amino acid derivatives can be considered versatile building blocks due to the presence of the alpha,alpha-disubstituted amino acid function, suitable for peptide synthesis, but also by the carbon-carbon norbornene double bond, which could be variously functionalized. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.052
• 作为产物：
  描述：

  苯硫酚 、 3-ethoxy-2-nitro-acrylic acid ethyl ester 反应 5.0h， 生成 ethyl α-nitro-β-(phenylthio)acrylate 、 2(Z)-ethyl β-sulfanyl-α-nitroacrylate
  参考文献：
  名称：

  Sulfanyl-methylene-5(4H)-oxazolones and β-sulfanyl-α-nitroacrylates as appealing dienophiles for the synthesis of conformationally constrained cysteine analogues

  摘要：

  A new class of masked constrained cysteine derivatives containing the norbornen/ane scaffold were prepared by the way of Diets-Alder cycloaddition reaction by exploitation of two different dienophiles, sulfanyl-methylene-5(4H)-oxazolones and beta-sulfanyl-alpha-nitroacrylates. The new norbornen/ane amino acid derivatives can be considered versatile building blocks due to the presence of the alpha,alpha-disubstituted amino acid function, suitable for peptide synthesis, but also by the carbon-carbon norbornene double bond, which could be variously functionalized. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.052

文献信息

• Sulfanyl-methylene-5(4H)-oxazolones and β-sulfanyl-α-nitroacrylates as appealing dienophiles for the synthesis of conformationally constrained cysteine analogues
  作者：Alessandro Ruffoni、Alessandro Casoni、Sara Pellegrino、Maria Luisa Gelmi、Raffaella Soave、Francesca Clerici

  DOI：10.1016/j.tet.2011.12.052

  日期：2012.2

  A new class of masked constrained cysteine derivatives containing the norbornen/ane scaffold were prepared by the way of Diets-Alder cycloaddition reaction by exploitation of two different dienophiles, sulfanyl-methylene-5(4H)-oxazolones and beta-sulfanyl-alpha-nitroacrylates. The new norbornen/ane amino acid derivatives can be considered versatile building blocks due to the presence of the alpha,alpha-disubstituted amino acid function, suitable for peptide synthesis, but also by the carbon-carbon norbornene double bond, which could be variously functionalized. (C) 2012 Elsevier Ltd. All rights reserved.