N,N'-bis-((S)-1-phenyl-ethyl)-fumaramide | 7683-78-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N,N'-bis-((S)-1-phenyl-ethyl)-fumaramide
• 英文别名: N,N'-Bis-((S)-1-phenyl-aethyl)-fumaramid；(E)-N,N'-bis[(1S)-1-phenylethyl]but-2-enediamide
• CAS: 7683-78-5
• 化学式: C₂₀H₂₂N₂O₂
• 分子量: 322.407
• InChiKey: BWKUFQKDNTWLMO-QKMFHXBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  氯-(4-甲基苯基)磺酰基亚胺钠 、 N,N'-bis-((S)-1-phenyl-ethyl)-fumaramide 在 K2 作用下， 以 水 、 叔丁醇 为溶剂， 生成 、
  参考文献：
  名称：

  First asymmetric aminohydroxylation of acrylamides

  摘要：

  The first examples of the asymmetric aminohydroxylation of acryl amides are reported. This was accomplished with chiral acrylamides as substrates, which undergo diastereoselective oxidative transformation within the so-called 'second catalytic cycle' with diastereomeric excesses reaching 100:0. The reaction relies solely on the stereochemical information provided by the enantiomerically pure starting materials. A stereochemical model for the observed asymmetric induction is provided. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.08.052
• 作为产物：
  描述：

  (S)-N-isopropyl-N-(1-phenylethyl)acrylamide 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到N,N'-bis-((S)-1-phenyl-ethyl)-fumaramide
  参考文献：
  名称：

  Efficient synthesis of fumaric amides through cross-metathesis of acrylic amides with the NHC Grubbs ruthenium catalyst

  摘要：

  Application of the second generation Grubbs metathesis catalyst for the homo-cross-metathesis of acroyl amides from chiral amines is reported. This efficient and high-yielding reaction provides a side-product free synthesis of fumaric acid diamides which are formed with complete (E)-selectivity under the reaction conditions. In particular, products which cannot be synthesized from the corresponding fumaroyl chloride via classic condensation route can now be provided in excellent yields (88-98%) with a catalyst loading from 2.5 mol% to even 0.375 mol%. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.07.116

文献信息

• The Stereoisomers of N ,N'-Bis(α-Phenylethyl)-Fumaramide
  作者：R. L. Shriner、Robert D. Thompson

  DOI：10.1021/jo50006a013

  日期：1951.12
• First asymmetric aminohydroxylation of acrylamides
  作者：Jan Streuff、Brigitte Osterath、Martin Nieger、Kilian Muñiz

  DOI：10.1016/j.tetasy.2005.08.052

  日期：2005.10

  The first examples of the asymmetric aminohydroxylation of acryl amides are reported. This was accomplished with chiral acrylamides as substrates, which undergo diastereoselective oxidative transformation within the so-called 'second catalytic cycle' with diastereomeric excesses reaching 100:0. The reaction relies solely on the stereochemical information provided by the enantiomerically pure starting materials. A stereochemical model for the observed asymmetric induction is provided. (c) 2005 Elsevier Ltd. All rights reserved.
• Efficient synthesis of fumaric amides through cross-metathesis of acrylic amides with the NHC Grubbs ruthenium catalyst
  作者：Jan Streuff、Kilian Muñiz

  DOI：10.1016/j.jorganchem.2005.07.116

  日期：2005.12

  Application of the second generation Grubbs metathesis catalyst for the homo-cross-metathesis of acroyl amides from chiral amines is reported. This efficient and high-yielding reaction provides a side-product free synthesis of fumaric acid diamides which are formed with complete (E)-selectivity under the reaction conditions. In particular, products which cannot be synthesized from the corresponding fumaroyl chloride via classic condensation route can now be provided in excellent yields (88-98%) with a catalyst loading from 2.5 mol% to even 0.375 mol%. (c) 2005 Elsevier B.V. All rights reserved.