2-benzoylamino-3-(4-fluorophenyl)propionic acid prop-2-ynyl ester | 497056-38-9

• 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-benzoylamino-3-(4-fluorophenyl)propionic acid prop-2-ynyl ester
• 英文别名: prop-2-yn-1-yl 4-fluoro-N-(phenylcarbonyl)phenylalaninate；prop-2-ynyl 2-benzamido-3-(4-fluorophenyl)propanoate
• CAS: 497056-38-9
• 化学式: C₁₉H₁₆FNO₃
• 分子量: 325.339
• InChiKey: CEVNMXBJSIBZTD-UHFFFAOYSA-N

物化性质

• 沸点：
  531.4±50.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-benzoylamino-3-(4-fluorophenyl)propionic acid prop-2-ynyl ester 在 sodium hydride 、 三乙胺 、 三苯基膦 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 6.75h， 生成 2-benzoyl-1-(4-fluorobenzyl)-6-methylene-5-oxo-1,2,3,5,6,6a-hexahydrocyclopenta[c]pyrrole-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Heterocyclic α-Alkylidene Cyclopentenones Obtained via a Pauson−Khand Reaction of Amino Acid Derived Allenynes. A Scope and Limitation Study Directed toward the Preparation of a Tricyclic Pyrrole Library

  摘要：

  [GRAPHICS]The synthesis of a novel class of tricyclic pyrroles has been accomplished by using a Pauson-Khand/Stetter/Paal-Knorr reaction sequence. Full details of the Pauson-Khand reaction of amino acid tethered allenynes 4a-e and 9a-d are disclosed. The study of this reaction led to the discovery of an unprecedented substituent effect on the diastereoselectivity of the MO(CO)(6) mediated allenic Pauson-Khand reaction. It was found that amino acid tethered allenynes with aromatic side chains afford alpha-alkylidene cyclopentenones with the opposite diastereoselectivity compared to those with aliphatic side chains. This effect has been attributed to complexation of the metal mediator to the aromatic ring in the substrate. Furthermore, an isomerization of one of the diastereomers of the a-alkylidene cyclopentenones was encountered, leading to eventual decomposition. The stable diastereomers were found to react well in the Stetter reaction leading to 1,4-diketones that were converted to pyrroles. The observation that the first generation of 2-alkyl-substituted pyrroles was unstable led to a second generation of 2-carboxamide pyrroles with sufficient stability for biological tests which are in progress.

  DOI：

  10.1021/jo0481607
• 作为产物：
  描述：

  N-Benzoyl-p-fluor-DL-phenylalanin 、 2-丙炔-1-醇 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以42%的产率得到2-benzoylamino-3-(4-fluorophenyl)propionic acid prop-2-ynyl ester
  参考文献：
  名称：

  Heterocyclic α-Alkylidene Cyclopentenones Obtained via a Pauson−Khand Reaction of Amino Acid Derived Allenynes. A Scope and Limitation Study Directed toward the Preparation of a Tricyclic Pyrrole Library

  摘要：

  [GRAPHICS]The synthesis of a novel class of tricyclic pyrroles has been accomplished by using a Pauson-Khand/Stetter/Paal-Knorr reaction sequence. Full details of the Pauson-Khand reaction of amino acid tethered allenynes 4a-e and 9a-d are disclosed. The study of this reaction led to the discovery of an unprecedented substituent effect on the diastereoselectivity of the MO(CO)(6) mediated allenic Pauson-Khand reaction. It was found that amino acid tethered allenynes with aromatic side chains afford alpha-alkylidene cyclopentenones with the opposite diastereoselectivity compared to those with aliphatic side chains. This effect has been attributed to complexation of the metal mediator to the aromatic ring in the substrate. Furthermore, an isomerization of one of the diastereomers of the a-alkylidene cyclopentenones was encountered, leading to eventual decomposition. The stable diastereomers were found to react well in the Stetter reaction leading to 1,4-diketones that were converted to pyrroles. The observation that the first generation of 2-alkyl-substituted pyrroles was unstable led to a second generation of 2-carboxamide pyrroles with sufficient stability for biological tests which are in progress.

  DOI：

  10.1021/jo0481607