(5R) methyl δ-hydroxy-δ-furan-2-yl-β-oxo-pentanoate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: (5R) methyl δ-hydroxy-δ-furan-2-yl-β-oxo-pentanoate
• 英文别名: methyl (5R)-5-(furan-2-yl)-5-hydroxy-3-oxopentanoate
• 化学式: C₁₀H₁₂O₅
• 分子量: 212.202
• InChiKey: OZGMBZHGBPGWOS-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  糠醛 、 1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene 在 C₄₇H₃₈O₄ 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (5R) methyl δ-hydroxy-δ-furan-2-yl-β-oxo-pentanoate 、 (5S) methyl δ-hydroxy-δ-furan-2-yl-β-oxo-pentanoate
  参考文献：
  名称：

  Solvent-free asymmetric vinylogous aldol reaction of Chan's diene with aromatic aldehydes catalyzed by hydrogen bonding

  摘要：

  Chan's diene proved to react with aromatic aldehydes under organocatalytic conditions in presence of a chiral naphthyl-TADDOL derivative to give vinylogous aldols (up to 65% ee) with complete gamma-selectivity. A further process of hetero-Diels-Alder cycloaddition, leading to chiral pyran-4-one derivatives (up to 60% ee), was favoured by electron-withdrawing substituents on the aromatic ring. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.01.112

文献信息

• Candida Rugosa lipase-catalyzed kinetic resolution of β-hydroxy-β-arylpropionates and δ-hydroxy-δ-aryl-β-oxo-pentanoates
  作者：Chengfu Xu、Chengye Yuan

  DOI：10.1016/j.tet.2004.12.059

  日期：2005.2

  A simple and convenient method was reported for the preparation of optically active beta-hydroxy-beta-arylpropionates, delta-hydroxy-delta-aryl-beta-oxo-pentanoates and their butyryl derivatives via CRL-catalyzed hydrolysis. The optically active products are potential precursors of some chiral pharmaceuticals and natural products. (C) 2005 Elsevier Ltd. All rights reserved.
• Solvent-free asymmetric vinylogous aldol reaction of Chan's diene with aromatic aldehydes catalyzed by hydrogen bonding
  作者：Rosaria Villano、Maria Rosaria Acocella、Antonio Massa、Laura Palombi、Arrigo Scettri

  DOI：10.1016/j.tet.2009.01.112

  日期：2009.7

  Chan's diene proved to react with aromatic aldehydes under organocatalytic conditions in presence of a chiral naphthyl-TADDOL derivative to give vinylogous aldols (up to 65% ee) with complete gamma-selectivity. A further process of hetero-Diels-Alder cycloaddition, leading to chiral pyran-4-one derivatives (up to 60% ee), was favoured by electron-withdrawing substituents on the aromatic ring. (C) 2009 Elsevier Ltd. All rights reserved.