(2RS,3SR)-2-[(1-ethoxycarbonyl)allyl]-N-phenylpropionamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2RS,3SR)-2-[(1-ethoxycarbonyl)allyl]-N-phenylpropionamide
• 英文别名: ethyl (2R)-2-[(2S)-1-anilino-2-hydroxy-1-oxopropan-2-yl]but-3-enoate
• 化学式: C₁₅H₁₉NO₄
• 分子量: 277.32
• InChiKey: SPQURVAMZADLBC-WFASDCNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-羟基-N-苯基丙酰胺 在 indium 、 jones reagent 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (2RS,3SR)-2-[(1-ethoxycarbonyl)allyl]-N-phenylpropionamide
  参考文献：
  名称：

  Regio- and stereochemical aspects in synthesis of 2-allyl derivatives of glycolic, mandelic and lactic acids and their iodocyclisations to 3-hydroxy-3,4-dihydrofuran-2(5H)-ones

  摘要：

  Glyoxalic, phenylglyoxalic and pyruvic acids la-c undergo regio- and diastereoselective indium mediated allylations with allyl and cinnamyl bromides and ethyl 4-bromocrotonate to provide respective 2-allyl-, 2-(1-phenylailyl)- and 2+1-ethoxycarbonyl)allyl]derivatives of glycolic, mandelic and lactic acids 3-11. The reactions follow Cram's chelation model for allylation and give syn addition products as the major or the only products. Diastereoselective iodocyclisations of 3-8 and 10 provide 3-hydroxy-3,4-dihydrofuran-2(5H)ones (15-21), the stereochemical outcome, of which depends on the nature and position of the substituents on the substrate, choice of solvent and base. The relative stereochemistries have been ascertained by X-ray structure and NOE experiments and coupling constants in the H-1 NMR spectra. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.045

文献信息

• Regio- and stereochemical aspects in synthesis of 2-allyl derivatives of glycolic, mandelic and lactic acids and their iodocyclisations to 3-hydroxy-3,4-dihydrofuran-2(5H)-ones
  作者：Pervinder Kaur、Palwinder Singh、Subodh Kumar

  DOI：10.1016/j.tet.2005.06.045

  日期：2005.8

  Glyoxalic, phenylglyoxalic and pyruvic acids la-c undergo regio- and diastereoselective indium mediated allylations with allyl and cinnamyl bromides and ethyl 4-bromocrotonate to provide respective 2-allyl-, 2-(1-phenylailyl)- and 2+1-ethoxycarbonyl)allyl]derivatives of glycolic, mandelic and lactic acids 3-11. The reactions follow Cram's chelation model for allylation and give syn addition products as the major or the only products. Diastereoselective iodocyclisations of 3-8 and 10 provide 3-hydroxy-3,4-dihydrofuran-2(5H)ones (15-21), the stereochemical outcome, of which depends on the nature and position of the substituents on the substrate, choice of solvent and base. The relative stereochemistries have been ascertained by X-ray structure and NOE experiments and coupling constants in the H-1 NMR spectra. (c) 2005 Elsevier Ltd. All rights reserved.