(5S)-4-allyloxy-5-(p-hydroxybenzyl)pyrrolin-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (5S)-4-allyloxy-5-(p-hydroxybenzyl)pyrrolin-2-one
• 英文别名: (2S)-2-[(4-hydroxyphenyl)methyl]-3-prop-2-enoxy-1,2-dihydropyrrol-5-one
• 化学式: C₁₄H₁₅NO₃
• 分子量: 245.278
• InChiKey: ZSQJPEJSXMWBJB-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (三苯基膦烯)乙烯酮 、 L-tyrosine allyl ester 在 苯甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以40%的产率得到(5S)-4-allyloxy-5-(p-hydroxybenzyl)pyrrolin-2-one
  参考文献：
  名称：

  Influence of steric parameters on the synthesis of tetramates from α-amino-β-alkoxy-esters and Ph3PCCO

  摘要：

  alpha-Aminoesters react with Ph3PCCO in a domino addition-Wittig cyclization sequence affording enantiomerically pure tetramates. In the case of beta-oxo functionalized alpha-aminoesters, e.g., esters of serine, threonine or beta-hydroxyornithine the yields of this reaction depend heavily on the bulkiness of the beta-OR group and on the configuration of beta-carbon atom C-3. Smaller residues and 2R/3R-configured aminoesters give better yields. The alkoxycarbonyl group of the ester moiety and the residue on the N-atom are less important. These findings can be accounted for by assuming an early puckered transition state for the intramolecular ring-closing Wittig reaction. The addition of sub-stoichiometric amounts of benzoic acid or N-hydroxysuccinimide (for acid-sensitive compounds) is advantageous in some cases as it accelerates the formation of the intermediate amide ylides. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.099

文献信息

• Influence of steric parameters on the synthesis of tetramates from α-amino-β-alkoxy-esters and Ph3PCCO
  作者：Inga Loke、Natja Park、Karl Kempf、Carsten Jagusch、Rainer Schobert、Sabine Laschat

  DOI：10.1016/j.tet.2011.10.099

  日期：2012.1

  alpha-Aminoesters react with Ph3PCCO in a domino addition-Wittig cyclization sequence affording enantiomerically pure tetramates. In the case of beta-oxo functionalized alpha-aminoesters, e.g., esters of serine, threonine or beta-hydroxyornithine the yields of this reaction depend heavily on the bulkiness of the beta-OR group and on the configuration of beta-carbon atom C-3. Smaller residues and 2R/3R-configured aminoesters give better yields. The alkoxycarbonyl group of the ester moiety and the residue on the N-atom are less important. These findings can be accounted for by assuming an early puckered transition state for the intramolecular ring-closing Wittig reaction. The addition of sub-stoichiometric amounts of benzoic acid or N-hydroxysuccinimide (for acid-sensitive compounds) is advantageous in some cases as it accelerates the formation of the intermediate amide ylides. (C) 2011 Elsevier Ltd. All rights reserved.