Pent-4-enoic acid ((S)-1-phenyl-ethyl)-prop-1-ynyl-amide | 441771-20-6

• 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: Pent-4-enoic acid ((S)-1-phenyl-ethyl)-prop-1-ynyl-amide
• 英文别名: N-[(1S)-1-phenylethyl]-N-prop-1-ynylpent-4-enamide
• CAS: 441771-20-6
• 化学式: C₁₆H₁₉NO
• 分子量: 241.333
• InChiKey: DDYLDQNTNTXXRT-AWEZNQCLSA-N

物化性质

• 沸点：
  345.1±45.0 °C(Predicted)
• 密度：
  1.014±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Pent-4-enoic acid ((S)-1-phenyl-ethyl)-prop-1-ynyl-amide 在 水 、 magnesium iodide 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到Pent-4-enoic acid ((E)-1-iodo-propenyl)-((S)-1-phenyl-ethyl)-amide
  参考文献：
  名称：

  Highly Stereoselective Synthesis of Novel α-Haloenamides via a Mild and Efficient Hydrohalogenation of Ynamides

  摘要：

  A highly stereoselective preparation of novel chiral (E)-alpha-haloenamides under mild conditions utilizing magnesium halide salts is described. This unexpected mild and efficient hydrohalogenation reaction highlights another synthetic utility of ynamides.

  DOI：

  10.1021/ol0300266
• 作为产物：
  描述：

  4-戊烯酰氯 在 4-二甲氨基吡啶 、 potassium tert-butylate 、 三乙胺 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 生成 Pent-4-enoic acid ((S)-1-phenyl-ethyl)-prop-1-ynyl-amide
  参考文献：
  名称：

  The First Successful Base-Promoted Isomerization of Propargyl Amides to Chiral Ynamides. Applications in Ring-Closing Metathesis of Ene−Ynamides and Tandem RCM of Diene−Ynamides

  摘要：

  [GRAPHICS]A highly useful sequence of reactions is described here. These reactions consist of the first successful base-induced isomerizations of propargyl amides to chiral ynamides, applications of these novel ynamides in ring-closure metathesis leading to chiral 2-amidodienes useful for Diels-Alder cycloadditions, and the first successful tandem RCM of diene-ynamides.

  DOI：

  10.1021/ol020097p

文献信息

• The First Successful Base-Promoted Isomerization of Propargyl Amides to Chiral Ynamides. Applications in Ring-Closing Metathesis of Ene−Ynamides and Tandem RCM of Diene−Ynamides
  作者：Jian Huang、Hui Xiong、Richard P. Hsung、C. Rameshkumar、Jason A. Mulder、Tyler P. Grebe

  DOI：10.1021/ol020097p

  日期：2002.7.1

  [GRAPHICS]A highly useful sequence of reactions is described here. These reactions consist of the first successful base-induced isomerizations of propargyl amides to chiral ynamides, applications of these novel ynamides in ring-closure metathesis leading to chiral 2-amidodienes useful for Diels-Alder cycloadditions, and the first successful tandem RCM of diene-ynamides.
• Highly Stereoselective Synthesis of Novel α-Haloenamides via a Mild and Efficient Hydrohalogenation of Ynamides
  作者：Jason A. Mulder、Kimberly C. M. Kurtz、Richard P. Hsung、Heather Coverdale、Michael O. Frederick、Lichun Shen、Craig A. Zificsak

  DOI：10.1021/ol0300266

  日期：2003.5.1

  A highly stereoselective preparation of novel chiral (E)-alpha-haloenamides under mild conditions utilizing magnesium halide salts is described. This unexpected mild and efficient hydrohalogenation reaction highlights another synthetic utility of ynamides.