(4S,5R)-5-pentyl-4-hydroxy-4,5-dihydrofuran-2(3H)-one | 186194-17-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (4S,5R)-5-pentyl-4-hydroxy-4,5-dihydrofuran-2(3H)-one
• 英文别名: (4S,5R)-4-hydroxy-5-pentyloxolan-2-one
• CAS: 186194-17-2
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: NVARDNCEKDHHJR-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,5R)-5-pentyl-4-hydroxy-4,5-dihydrofuran-2(3H)-one 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到(-)-(R)-5-pentyl-2(5H)-furanone
  参考文献：
  名称：

  Organo-catalyzed enantioselective synthesis of some β-silyl γ-alkyl γ-butyrolactones as intermediates for natural products

  摘要：

  The enantioselective synthesis of some beta-silyl gamma-alkyl gamma-butyrolactones has been achieved by an organo-catalyzed Michael addition of enolizable aldehydes onto a silylmethylene malonate followed by a silicon-facilitated Bayer-Villiger oxidation of the beta-silyl aldehyde adducts as the key step. gamma-Alkyl gamma-butenolides were obtained from the beta-silyl gamma-alkyl gamma-butyrolactones by Fleming-Tamao oxidation of the silyl group to a hydroxy group and subsequent elimination. These butenolides are the advanced intermediates of some natural products such as (+)-gamma-caprolactone, (+)-methylenolactocine, and (-)-quercus lactone. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.10.013
• 作为产物：
  描述：

  (4S,5R)-4-dimethyl(phenyl)silyl-5-pentyl-4,5-dihydrofuran-2(3H)-one 在 过氧乙酸 、 双氧水 、 溶剂黄146 、 potassium bromide 作用下， 以62%的产率得到(4S,5R)-5-pentyl-4-hydroxy-4,5-dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Organo-catalyzed enantioselective synthesis of some β-silyl γ-alkyl γ-butyrolactones as intermediates for natural products

  摘要：

  The enantioselective synthesis of some beta-silyl gamma-alkyl gamma-butyrolactones has been achieved by an organo-catalyzed Michael addition of enolizable aldehydes onto a silylmethylene malonate followed by a silicon-facilitated Bayer-Villiger oxidation of the beta-silyl aldehyde adducts as the key step. gamma-Alkyl gamma-butenolides were obtained from the beta-silyl gamma-alkyl gamma-butyrolactones by Fleming-Tamao oxidation of the silyl group to a hydroxy group and subsequent elimination. These butenolides are the advanced intermediates of some natural products such as (+)-gamma-caprolactone, (+)-methylenolactocine, and (-)-quercus lactone. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.10.013

文献信息

• Organo-catalyzed enantioselective synthesis of some β-silyl γ-alkyl γ-butyrolactones as intermediates for natural products
  作者：Raghunath Chowdhury、Sunil K. Ghosh

  DOI：10.1016/j.tetasy.2011.10.013

  日期：2011.11

  The enantioselective synthesis of some beta-silyl gamma-alkyl gamma-butyrolactones has been achieved by an organo-catalyzed Michael addition of enolizable aldehydes onto a silylmethylene malonate followed by a silicon-facilitated Bayer-Villiger oxidation of the beta-silyl aldehyde adducts as the key step. gamma-Alkyl gamma-butenolides were obtained from the beta-silyl gamma-alkyl gamma-butyrolactones by Fleming-Tamao oxidation of the silyl group to a hydroxy group and subsequent elimination. These butenolides are the advanced intermediates of some natural products such as (+)-gamma-caprolactone, (+)-methylenolactocine, and (-)-quercus lactone. (C) 2011 Elsevier Ltd. All rights reserved.