2(Z)-ethyl β-sulfanyl-α-nitroacrylate | 73386-92-2

• 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: 2(Z)-ethyl β-sulfanyl-α-nitroacrylate
• 英文别名: ethyl α-nitro-β-(phenylthio)acrylate；ethyl (Z)-2-nitro-3-phenylsulfanylprop-2-enoate
• CAS: 73386-92-2
• 化学式: C₁₁H₁₁NO₄S
• 分子量: 253.279
• InChiKey: GLIPLLWNPXUZKD-NTMALXAHSA-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：

  2(Z)-ethyl β-sulfanyl-α-nitroacrylate 、 环戊二烯 反应 24.0h， 以11%的产率得到(1RS,2RS,3SR,4SR)-ethyl 2-nitro-3-(phenylthio)bicyclo[2.2.1]hept-5-ene-2-carboxylate
  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：

  3-ethoxy-2-nitro-acrylic acid ethyl ester 以 氯仿 为溶剂， 反应 53.0h， 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

文献信息

• 2-Amino-3-(phenylsulfanyl)norbornane-2-carboxylate: An Appealing Scaffold for the Design of Rac1–Tiam1 Protein–Protein Interaction Inhibitors
  作者：Alessandro Ruffoni、Nicola Ferri、Sergio K. Bernini、Chiara Ricci、Alberto Corsini、Irene Maffucci、Francesca Clerici、Alessandro Contini

  DOI：10.1021/jm401924s

  日期：2014.4.10

  The use of the 2-amino-3-(phenylsulfany1)norbornane-2-carboxylate scaffold has been exploited for the de novo design of potent Rac1 inhibitors acting as modulators of the protein protein interaction between Rac1 and Tiam1. A series of compounds differing in regio- and stereochemistry has been prepared by way of a multistep synthesis based on cycloaddition reactions and Pd chemistry. Pharmacological analyses showed that all the prepared compounds were active and selective for Rac1, and the most effective compound 13 was capable of inhibiting smooth muscle cell migration. The synthesis of this derivative was successfully scaled up to 1 g.
• 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.