(+)-(R)-5-(2-phenylethyl)dihydrofuran-2(3H)-one | 112607-22-4

• 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-(2-phenylethyl)dihydrofuran-2(3H)-one
• 英文别名: (R)-6-phenyl-γ-hexalacton；(R)-5-phenethyldihydrofuran-2(3H)-one；(5R)-5-(2-phenylethyl)oxolan-2-one
• CAS: 112607-22-4
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: ONECXZFGYJSVIF-LLVKDONJSA-N

物化性质

• 沸点：
  343.8±11.0 °C(Predicted)
• 密度：
  1.090±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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-(2-phenylethyl)dihydrofuran-2(3H)-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 7.0h， 生成 (R)-1-phenylhexan-3-ol
  参考文献：
  名称：

  Baker's yeast reduction of arylalkyl and arylalkenil γ- and δ-keto acids

  摘要：

  gamma- and delta-Lactones 5, 6, 13, 14, 15 and 16 were synthesized via baker's yeast reduction of the corresponding keto acids 3 ,4 and 9-12. The enantioselectivity of the reduction is strongly dependent on the nature of the keto acid: the delta-lactones were always obtained in an ee% higher than the gamma-lactones and ranging from 70% to 100%.

  DOI：

  10.1016/s0040-4020(01)81944-x
• 作为产物：
  描述：

  6-phenyl-4-oxohexanoic acid 在 盐酸 、 氢气 、 C₆₇H₈₀IrNOP⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) 、 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 生成 (+)-(R)-5-(2-phenylethyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  羧基引导的铱催化脂肪族γ-酮酸的对映选择性加氢

  摘要：

  尽管已经广泛地研究了过渡金属催化的芳族酮的不对称氢化，但是脂肪族酮的对映选择性氢化仍然是一个挑战，因为手性催化剂不能轻易地区分这些酮的正反面。在这里，我们报道了脂肪族γ-酮酸不对称氢化的羧基导向策略。在具有手性螺膦-恶唑啉配体的铱配合物的催化下，脂肪族γ-酮酸的氢化得到具有高对映选择性（高达99％ee）的手性γ-羟基内酯。机理研究表明，底物的羧基指导氢转移并确保高对映选择性。

  DOI：

  10.1021/acscatal.0c02142

文献信息

• Palladium/Zinc Co‐Catalyzed Asymmetric Hydrogenation of γ‐Keto Carboxylic Acids
  作者：Keyang Zhang、Xuexin Zhang、Jingchao Chen、Zixiu Liu、Chunxiang Pan、Yuanbin Zhu、Shiyuan Wu、Baomin Fan

  DOI：10.1002/asia.202100244

  日期：2021.5.17

  A palladium‐catalyzed asymmetric hydrogenation of levulinic acid has been successful developed by using Zn(OTf)2 as co‐catalyst. The present method not only has provided a strategy in the palladium‐catalyzed asymmetric hydrogenation of ketone, but also allowed the preparation of a wide range of chiral γ‐valerolactones in good yields with excellent enantioselectivities.

  通过使用Zn（OTf）2作为助催化剂，成功开发了钯催化的乙酰丙酸不对称加氢反应。本方法不仅为钯催化酮的​​不对称加氢提供了策略，而且还允许以良好的收率和良好的对映选择性制备各种手性γ-戊内酯。
• Preparation of optically active 4-substituted γ-lactones by lipase-catalyzed optical resolution
  作者：Yasutaka Shimotori、Masayuki Hoshi、Keita Inoue、Takeshi Osanai、Hayato Okabe、Tetsuo Miyakoshi

  DOI：10.1515/hc-2015-0027

  日期：2015.6.1

  Abstract Optically active 4-substituted γ-lactones (3 and 4) were synthesized effectively using lipase-catalyzed optical resolution. N-methyl-4-hydroxyalkanamides (rac-1a–i) as substrates were prepared from N-methylsuccinimide. The alkylation of N-methylsuccinimide using Grignard reagents generated from various alkyl halides followed by reduction resulted in N-methyl-4-hydroxyalkanamides. The optical resolution

  摘要 使用脂肪酶催化的光学拆分有效地合成了具有光学活性的 4-取代 γ-内酯（3 和 4）。N-甲基-4-羟基链烷酰胺（rac-1a-i）作为底物由N-甲基琥珀酰亚胺制备。使用由各种烷基卤化物生成的格氏试剂对 N-甲基琥珀酰亚胺进行烷基化，然后还原生成 N-甲基-4-羟基链烷酰胺。使用 Novozym 435 催化的立体选择性乙酰化对 rac-1a-g 进行光学拆分。立体选择性制备了具有异戊基、苯基和苯乙基等各种侧链的 4-取代 γ-内酯（3 和 4），对映体纯度超过 90%。
• 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.
• Krief, Alain; Ronvaux, Alain; Tuch, Arounarith, Bulletin des Societes Chimiques Belges, 1997, vol. 106, # 11, p. 699 - 702
  作者：Krief, Alain、Ronvaux, Alain、Tuch, Arounarith

  DOI：——

  日期：——