(S)-N-(1-phenylethyl)-but-2-enamide

• 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: (S)-N-(1-phenylethyl)-but-2-enamide
• 英文别名: N-[(1S)-1-phenylethyl]but-2-enamide
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: DAUQSSMGAMQHGD-JTQLQIEISA-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：

  (S)-N-(1-phenylethyl)-but-2-enamide 在 对甲苯磺酸 sodium hydroxide 、 羟胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 水 、 丙酮 、 苯 为溶剂， 反应 5.5h， 生成 (1'S,5R,8S)-8-methyl-3-(1'-phenylethyl)-7-oxa-1,3-diazabicyclo-<3.2.1>-octane-4,6-dione
  参考文献：
  名称：

  Synthesis and stereochemical behaviour of 8-alkyl-3-(1-phenylethyl)-7-oxa-1,3-diazabicyclo-[3.2.1]-octane-4,6-diones directed towards the synthesis of α-substituted β-amino acids

  摘要：

  A diastereoselective synthesis of enantiomerically pure a-hydroxymethyl p-amino acid derivatives is described starting from a,P-unsaturated acids. The unsaturated adds are transformed through simple steps into chiral perhydropyrimidin-4-ones that are diastereoselectively transformed into [3.2.1]-1,3-diaza-7-oxabicyclooctan-4,6-diones by reaction with LiHMDS. The bicycle 9b is opened by reaction with methanol under acid catalysis and the product 10 is selectively reduced to afford the desired compound.

  DOI：

  10.1016/s0040-4020(01)87007-1
• 作为产物：
  描述：

  (S)-(-)- α-甲基苄胺 、 巴豆酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以92%的产率得到(S)-N-(1-phenylethyl)-but-2-enamide
  参考文献：
  名称：

  Synthesis and stereochemical behaviour of 8-alkyl-3-(1-phenylethyl)-7-oxa-1,3-diazabicyclo-[3.2.1]-octane-4,6-diones directed towards the synthesis of α-substituted β-amino acids

  摘要：

  A diastereoselective synthesis of enantiomerically pure a-hydroxymethyl p-amino acid derivatives is described starting from a,P-unsaturated acids. The unsaturated adds are transformed through simple steps into chiral perhydropyrimidin-4-ones that are diastereoselectively transformed into [3.2.1]-1,3-diaza-7-oxabicyclooctan-4,6-diones by reaction with LiHMDS. The bicycle 9b is opened by reaction with methanol under acid catalysis and the product 10 is selectively reduced to afford the desired compound.

  DOI：

  10.1016/s0040-4020(01)87007-1

文献信息

• Catalyst-Free Conjugate Addition of Thioacids to Activated Olefins Accelerated in Water
  作者：Katayoun Marjani、Maryam Khalesi、Akram Ashouri、Aazam Jalali、Azim Ziyaei-Halimehjani

  DOI：10.1080/00397911003587515

  日期：2011.1.25

  Michael addition of thioacetic and thiobenzoic acids to activated olefins was investigated in the presence of water under catalyst-free conditions. This process, in addition to being green, has an excellent yield. With simple filtration, high-quality products were obtained on a large scale. Competitive dithiane formation and ester cleavage were not observed. Also, excellent yield was obtained using

  在无催化剂条件下，在水的存在下研究了硫代乙酸和硫代苯甲酸与活化烯烃的迈克尔加成反应。这个过程，除了是绿色的，还具有极好的产量。通过简单的过滤，可以大规模获得高质量的产品。没有观察到竞争性二噻烷形成和酯裂解。此外，在螺内酯合成的最后一步使用这种简单的方法获得了极好的收率。
• Synthesis and stereochemical behaviour of 8-alkyl-3-(1-phenylethyl)-7-oxa-1,3-diazabicyclo-[3.2.1]-octane-4,6-diones directed towards the synthesis of α-substituted β-amino acids
  作者：Ilaria Braschi、Giuliana Cardillo、Claudia Tomasini

  DOI：10.1016/s0040-4020(01)87007-1

  日期：1994.2

  A diastereoselective synthesis of enantiomerically pure a-hydroxymethyl p-amino acid derivatives is described starting from a,P-unsaturated acids. The unsaturated adds are transformed through simple steps into chiral perhydropyrimidin-4-ones that are diastereoselectively transformed into [3.2.1]-1,3-diaza-7-oxabicyclooctan-4,6-diones by reaction with LiHMDS. The bicycle 9b is opened by reaction with methanol under acid catalysis and the product 10 is selectively reduced to afford the desired compound.