(E)-But-2-enoic acid ((S)-1-phenyl-ethyl)-amide | 158382-01-5

• 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: (E)-But-2-enoic acid ((S)-1-phenyl-ethyl)-amide
• 英文别名: (E)-N-[(1S)-1-phenylethyl]but-2-enamide
• CAS: 158382-01-5
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: DAUQSSMGAMQHGD-HTZNOQTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-But-2-enoic acid ((S)-1-phenyl-ethyl)-amide 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 以92%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
• 作为产物：
  描述：

  2-丁烯酰氯 、 (S)-(-)- α-甲基苄胺 生成 (E)-But-2-enoic acid ((S)-1-phenyl-ethyl)-amide
  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

文献信息

• Catalytic Asymmetric Hydroalkylation of α,β-Unsaturated Amides Enabled by Regio-Reversed and Enantiodifferentiating <i>syn</i>-Hydronickellation
  作者：Fang Zhou、Shaolin Zhu

  DOI：10.1021/acscatal.1c02299

  日期：2021.7.16
• A novel tandem process leading to functionalized glutarimides
  作者：Jelena B. Popović-Đorđević、Milovan D. Ivanović、Vesna D. Kiricojević

  DOI：10.1016/j.tetlet.2005.02.087

  日期：2005.4

  The synthesis of various functionalized or spirobicyclic glutarimides by a novel tandem process has been disclosed. The reaction involves a base-catalyzed Michael addition of active methylene compounds to secondary conjugated amides, followed by intramolecular N-acylation of the carboxamido group. It provides a relatively general and simple access to useful synthetic intermediaries and potentially active pharmacological compounds. In addition, a novel group of spirobicyclic systems has been synthesized. (c) 2005 Elsevier Ltd. All rights reserved.
• Diastereoselective synthesis of α-substituted β-amidophosphonates
  作者：Géraldine Castelot-Deliencourt、Xavier Pannecoucke、Jean-Charles Quirion

  DOI：10.1016/s0040-4039(00)02145-6

  日期：2001.2

  A simple and general asymmetric synthesis of beta -amidophosphonates is described. The method involves the highly selective addition (up to 95% d.e.) of diethyl phosphite to various chiral alpha,beta -unsaturated carboxylic amides derived from chiral aminoalcohols. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Alternative synthesis of α-substituted β-amidophosphines by [1,4]-addition. A new route to chiral ligands
  作者：Matthieu Léautey、Géraldine Castelot-Deliencourt、Philippe Jubault、Xavier Pannecoucke、Jean-Charles Quirion

  DOI：10.1016/s0040-4039(02)02250-5

  日期：2002.12

  Phosphine-borane can be diastereoselectively added to chiral alpha,beta-unsaturated amides 3, using amino-alcohols as chiral inducers, leading to alpha-substituted beta-amidophosphine boranes 4 with up to 74% diastereomeric excess. Selective deprotection afforded optically pure carboxylic derivatives 5 which are key intermediates for the synthesis of various potential chiral ligands for asymmetric catalysis. (C) 2002 Published by Elsevier Science Ltd.
• 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.