(R)-4-ethyldihydrofuran-2(3H)-one | 774198-33-3

• 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)-4-ethyldihydrofuran-2(3H)-one
• 英文别名: (R)-4-ethyldihydro-2(3H)-furanone；(R)-4-Ethyldihydrofuran-2(3H)-one；(4R)-4-ethyloxolan-2-one
• CAS: 774198-33-3
• 化学式: C₆H₁₀O₂
• 分子量: 114.144
• InChiKey: MDQZVJSUBKPTHG-RXMQYKEDSA-N

物化性质

• 沸点：
  214.9±8.0 °C(Predicted)
• 密度：
  1.002±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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)-4-ethyldihydrofuran-2(3H)-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 R-(+)-2-ethyl-1,4-butanediol
  参考文献：
  名称：

  Synthesis and absolute configuration of the insecticidal sesquilignan (+)-HAEDOXAN a in honour of professor G. H. Neil Towers 75th birthday

  摘要：

  The insecticidal neolignan, (+)-haedoxan A, was synthesized from (S)-(+)-beta-vinyl-gamma-butyrolactone and (2R,3R)-(+)-6-formyl-7-methoxy-3-methoxymethyl-2-(3,4-methylenedioxyphenyl)-1,4-benzodioxane, and its absolute configuration was unequivocally established as 1S,2R,5R,6S,2"R,3''R. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(98)00270-2
• 作为产物：
  描述：

  4-乙烯基二氢呋喃-2(3H)-酮 在 palladium on activated charcoal 2-羟基吡啶 、 氢氧化钾 、 氢气 、 对甲苯磺酸 作用下， 以 乙醇 、 乙二醇 、 苯 为溶剂， 反应 20.17h， 生成 (R)-4-ethyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  Synthesis and absolute configuration of the insecticidal sesquilignan (+)-HAEDOXAN a in honour of professor G. H. Neil Towers 75th birthday

  摘要：

  The insecticidal neolignan, (+)-haedoxan A, was synthesized from (S)-(+)-beta-vinyl-gamma-butyrolactone and (2R,3R)-(+)-6-formyl-7-methoxy-3-methoxymethyl-2-(3,4-methylenedioxyphenyl)-1,4-benzodioxane, and its absolute configuration was unequivocally established as 1S,2R,5R,6S,2"R,3''R. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(98)00270-2

文献信息

• Synthesis and olfactory evaluation of optically active β-alkyl substituted γ-lactones and whiskey lactone analogues
  作者：Masashi Kawasaki、Daiki Kato、Takuya Okada、Yuko Morita、Yasuo Tanaka、Naoki Toyooka

  DOI：10.1016/j.tet.2020.130984

  日期：2020.3

  β-alkyl substituted γ-lactones and whiskey lactone analogues were synthesized, and the odor properties were evaluated. During the preparation of the chiral intermediates, we found good reaction conditions for the highly enantioselective esterification of 3-arylmethyl-2-methyl-1-propanols to kinetically resolve them. The results of the olfactory evaluations of the synthesized lactones revealed that the alkyl

  合成了具有光学活性的β-烷基取代的γ-内酯和威士忌内酯类似物，并评估了其气味特性。在手性中间体的制备过程中，我们发现了3-芳基甲基-2-甲基-1-丙醇的高度对映选择性酯化反应的良好反应条件，以动力学方式将它们拆分。合成内酯的嗅觉评价结果表明，γ-内酯环上的烷基对气味分布起重要作用。
• Synthesis of epimer of Taniaphos ligand
  作者：Ambroz Almássy、Erik Rakovský、Andrea Malastová、Zuzana Sorádová、Radovan Šebesta

  DOI：10.1016/j.jorganchem.2016.01.004

  日期：2016.3

  The spatial arrangement of groups within a chiral ligand is essential for its catalytic performance. This work describes convenient synthesis of (R,Sp)-1-(2-(diphenylphosphano)ferrocenyl)-1-(2-diphenylphosphanophenyl)-N,N-dimethylmethanamine, a diastereomer of the well known (R,Rp)-Taniaphos ligand. The compound was prepared from the same homochiral amine as Taniaphos by sequential twofold lithiation

  手性配体内基团的空间排列对其催化性能至关重要。这项工作描述了（R，S p）-1-（2-（二苯基膦基）二茂铁基）-1-（2-二苯基膦基苯基）-N，N-二甲基甲胺的合成方法，这是众所周知的（R，R p）的非对映异构体-Taniaphos配体。该化合物是由与Taniaphos相同的同手性胺通过依次两次锂化制备，然后用二苯二氯膦进行捕集而制得的。与同时进行的双锂化相反，相继的双重锂化导致立体平面的相反配置。（R，通过X射线结构分析证实了S p）-非对映异构体及其CuBr-配合物。DFT计算阐明了控制锂化立体化学结果的潜在效应。
• Highly enantioselective copper-catalyzed 1,4-conjugate addition of diethylzinc to cyclic enones and α,β-unsaturated lactones
  作者：Liang Liang、Ming Yan、Yue-Ming Li、Albert S.C. Chan

  DOI：10.1016/j.tetasy.2004.07.012

  日期：2004.8

  A significant improvement in enantioselectivity has been achieved in the 1,4-additions of diethylzinc to 2-cyclopentenone, 2-cyclohexenone and 5,6-hydro-2H-pyran-2-one (up to 93%, 98% and 94% ee, respectively) by using a chiral diphosphite-copper catalyst under suitable reaction conditions. (C) 2004 Elsevier Ltd. All rights reserved.
• Ferrocene phosphane–carbene ligands in Cu-catalyzed enantioselective 1,4-additions of Grignard reagents to α,β-unsaturated carbonyl compounds
  作者：Jana Csizmadiová、Mária Mečiarová、Ambroz Almássy、Branislav Horváth、Radovan Šebesta

  DOI：10.1016/j.jorganchem.2013.03.033

  日期：2013.8

  Chiral ferrocene phosphane-carbenes are good ligands for the copper-catalyzed 1,4-addition of Grignard reagents to various Michael acceptors. The products were obtained in high enantiomeric purity (up to e.r. = 95:5) and excellent regioselectivity (r.r. = 99:1). These ligands are also useful for domino conjugate addition followed by enolate trapping with imine and aldehyde. (C) 2013 Elsevier B.V. All rights reserved.
• Intramolecular Regioselective Insertion into Unactivated Prochiral Carbon−Hydrogen Bonds with Diazoacetates of Primary Alcohols Catalyzed by Chiral Dirhodium(II) Carboxamidates. Highly Enantioselective Total Synthesis of Natural Lignan Lactones
  作者：Jeffrey W. Bode、Michael P. Doyle、Marina N. Protopopova、Qi-Lin Zhou

  DOI：10.1021/jo961607u

  日期：1996.1.1

  Intramolecular insertion into unactivated prochiral C-H bonds of 3-aryl-1-propyl diazoacetates catalyzed by dirhodium(II) tetrakis[methyl 1-(3-phenyl propanoyl)imidazolidin-2-one-4(R or S)-carboxylate], Rh-2(4R-MPPIM)(4) or Rh-2(4S-MPPIM)(4), occurs in 91-96% ee and with virtually complete regiocontrol for the formation of beta-benzyl-gamma-butyrolactones. This methodology has been applied to the total synthesis of dibenzylbutyrolactone lignans (-)- and (+)-enterolactone, (-)- and (+)-hinokinin, and (+)-arctigenin from substituted cinnamic acids in 19-27% overall yields. Aryltetralin lignan (+)-isodeoxypodophyllotoxin was prepared from the reactant 3,4-(methylenedioxy)cinnamic acid in 36% yield overall, and the lactone precursor to (+)-isolauricerisinol was formed in 96.5% ee and 23% yield overall. Applications of the chiral Rh-2(MPPIM)4 catalysts to fully aliphatic systems resulting in the formation of beta-substituted-gamma-butyrolactones with high regiocontrol and with 93-96% ee have demonstrated the generality of this methodology. A model that provides accurate predictions of beta-substituted-gamma-butyrolactone absolute configurations in these asymmetric metal carbene transformations is described.