(+)-(R)-5-(3-phenylpropyl)dihydrofuran-2(3H)-one | 138298-25-6

• 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: (+)-(R)-5-(3-phenylpropyl)dihydrofuran-2(3H)-one
• 英文别名: (5R)-5-(3-phenylpropyl)oxolan-2-one
• CAS: 138298-25-6
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: JZULXIIBECGZTP-GFCCVEGCSA-N

物化性质

• 沸点：
  356.1±11.0 °C(Predicted)
• 密度：
  1.069±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-(R)-5-(3-phenylpropyl)dihydrofuran-2(3H)-one 在 三氯化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 16.0h， 以64%的产率得到(S)-3-(1,2,3,4-tetrahydro-naphthalen-1-yl)-propionic acid
  参考文献：
  名称：

  A synthetic approach to the pseudopterosins using cascade technology

  摘要：

  A rapid synthetic entry towards the pseudopterosins, a class of diterpenes which display potent anti-inflammatory and analgesic properties, is described. The key feature of this approach is the use of a sequential intramolecular, Lewis acid mediated Friedel-Crafts alkylation - Friedel-Crafts acylation sequence, viz 14 to 15, to establish the tricyclic carbon framework.

  DOI：

  10.1016/s0040-4039(00)73163-7
• 作为产物：
  描述：

  (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 在 吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium iodide 作用下， 以 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 28.0h， 生成 (+)-(R)-5-(3-phenylpropyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  A synthetic approach to the pseudopterosins using cascade technology

  摘要：

  A rapid synthetic entry towards the pseudopterosins, a class of diterpenes which display potent anti-inflammatory and analgesic properties, is described. The key feature of this approach is the use of a sequential intramolecular, Lewis acid mediated Friedel-Crafts alkylation - Friedel-Crafts acylation sequence, viz 14 to 15, to establish the tricyclic carbon framework.

  DOI：

  10.1016/s0040-4039(00)73163-7

文献信息

• Process-scale preparation of enantiomerically pure γ-lactones by asymmetric hydrogenation of γ-ketoesters and comparative tests of the sensory properties of some antipodes
  作者：Tiziana Benincori、Simona Rizzo、Tullio Pilati、Alessandro Ponti、Mara Sada、Ella Pagliarini、Simona Ratti、Celentano Giuseppe、Lorenzo de Ferra、Franco Sannicolò

  DOI：10.1016/j.tetasy.2004.06.024

  日期：2004.7

  A reliable methodology, applicable on a process-scale level, for producing enantiomerically pure chiral gamma-lactones by enantioselective hydrogenation of gamma-ketoesters, followed by cyclisation of the resulting gamma-hydroxyesters, has been developed. The multi-step procedure was transformed into a one-pot reaction. A very efficient chiral Ru-complex, based on the bilieteroaromatic diphosphine ligand tetraMe-BITIOP, was developed as a catalyst, capable of coupling fast kinetics with high stereoselection levels. Its structure was fully elucidated through P-31 NMR, EPR and X-ray single-crystal analyses. The optimal experimental conditions are as follows: hydrogen pressure = 30 psi, S/C ratio = 2000, 30% in weight substrate concentration. Yields are quantitative and enantiomeric excesses in the range 98-99.9%. Sensorial tests on the antipodes of two gamma-lactones demonstrated the very different properties of the enantiomers. (C) 2004 Published by Elsevier Ltd.
• Enantioselective Synthesis of <i>syn</i>/<i>anti</i>-1,3-Amino Alcohols via Proline-Catalyzed Sequential α-Aminoxylation/α-Amination and Horner−Wadsworth−Emmons Olefination of Aldehydes
  作者：Vishwajeet Jha、Nagendra B. Kondekar、Pradeep Kumar

  DOI：10.1021/ol100856u

  日期：2010.6.18

  A novel and general method for asymmetric synthesis of both syn/anti-1,3-amino alcohols is described. The method uses proline-catalyzed sequential alpha-aminoxylation/alpha-amination and Horner-Wadsworth-Emmons (HWE) olefination of aldehydes as the key step. By using this method, a short synthesis of a bioactive molecule, (R)-1-((S)-1-methylpyrrolidin-2-yl)-5-phenylpentan-2-ol, is also accomplished.
• A synthetic approach to the pseudopterosins using cascade technology
  作者：David C. Harrowven、Shelagh T. Dennison、Peter Howes

  DOI：10.1016/s0040-4039(00)73163-7

  日期：1994.6

  A rapid synthetic entry towards the pseudopterosins, a class of diterpenes which display potent anti-inflammatory and analgesic properties, is described. The key feature of this approach is the use of a sequential intramolecular, Lewis acid mediated Friedel-Crafts alkylation - Friedel-Crafts acylation sequence, viz 14 to 15, to establish the tricyclic carbon framework.