S-3-hydroxy-5,5-dimethyl-4,5-dihydro-2-(3H)-furanone | 497157-66-1

• 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: S-3-hydroxy-5,5-dimethyl-4,5-dihydro-2-(3H)-furanone
• 英文别名: (S)-2-hydroxy-4,4-dimethyl-γ-butyrolactone；(S)-3-hydroxy-5,5-dimethyldihydrofuran-2(3H)-one；(3S)-3-hydroxy-5,5-dimethyloxolan-2-one
• CAS: 497157-66-1
• 化学式: C₆H₁₀O₃
• 分子量: 130.144
• InChiKey: FQQIPIVZYKEWGI-BYPYZUCNSA-N

物化性质

• 沸点：
  227.8±15.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  4'-正癸氧基联苯-4-羧酸 、 S-3-hydroxy-5,5-dimethyl-4,5-dihydro-2-(3H)-furanone 在 N,N-dimethoxy-4-amino-pyridine 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 [(3S)-5,5-dimethyl-2-oxooxolan-3-yl] 4-(4-decoxyphenyl)benzoate
  参考文献：
  名称：

  新型光学活性 4,4-二烷基-γ-内酯作为铁电液晶的手性掺杂剂

  摘要：

  (S)-2-(4'-n-Decyloxybiphenyl-4-carboxy)-4,4-di烷基-γ-丁内酯被合成并被证明是铁电液晶的良好手性掺杂剂。

  DOI：

  10.1246/cl.1992.567
• 作为产物：
  描述：

  2S,5S,6R-2-(2-hydroxy-2-methyl-propyl)-4,5-dimethyl-6-phenyl-morpholin-3-one 在 硫酸 、 氨 、 sodium 、 三氯乙酸 作用下， 以 四氢呋喃 、 氯仿 、 水 为溶剂， 反应 35.05h， 生成 S-3-hydroxy-5,5-dimethyl-4,5-dihydro-2-(3H)-furanone
  参考文献：
  名称：

  Enantioselective synthesis of α-hydroxy γ-butyrolactones from an ephedrine-derived morpholine-dione

  摘要：

  An ephedrine-derived morpholine dione is employed in the enantioselective synthesis of (S)-alpha-hydroxy- gamma,gamma-dimethyl-gamma-butyrolactone and (S)-alpha-hydroxy gamma-butyrolactone. A one-pot alkylation/allylation protocol for the stereoselective conversion of the dione to 2-alkyl-2-allyl morpholinones, key intermediates for alpha-alkyl-alpha-hydroxy-gamma-butyrolactones, is described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01151-1

文献信息

• Kinetic Resolution of Racemic 2-Hydroxy-γ-butyrolactones by Asymmetric Esterification Using Diphenylacetic Acid with Pivalic Anhydride and a Chiral Acyl-Transfer Catalyst
  作者：Kenya Nakata、Kouya Gotoh、Keisuke Ono、Kengo Futami、Isamu Shiina

  DOI：10.1021/ol303453j

  日期：2013.3.15

  Various optically active 2-hydroxy-γ-butyrolactone derivatives are produced via the kinetic resolution of racemic 2-hydroxy-γ-butyrolactones with diphenylacetic acid using pivalic anhydride and (R)-benzotetramisole ((R)-BTM), a chiral acyl-transfer catalyst. Importantly, the substrate scope of this novel protocol is fairly broad (12 examples, s-value; up to over 1000). In addition, we succeeded in

  使用新戊酸酐和（R）-苯并四咪唑（（R）-BTM），手性酰基-转移催化剂。重要的是，该新颖方案的底物范围相当广泛（12个例子，s值；最大超过1000）。此外，我们通过理论计算成功地揭示了提供高对映选择性的反应机理，并阐述了2-羟基内酯在C-3位置的取代基效应。
• 10.1021/jacs.4c04043
  作者：Zhuang, Zhe、Sheng, Tao、Qiao, Jennifer X.、Yeung, Kap-Sun、Yu, Jin-Quan

  DOI：10.1021/jacs.4c04043

  日期：——

  carboxylic acids and cycloalkane acetic acids was observed, giving either fused or bridged γ-lactones that are difficult to access by other methods. δ-C–H lactonization was only favored in the presence of tertiary δ-C–H bonds. The synthetic utility of this methodology was demonstrated by the late-stage functionalization of amino acids, drug molecules, and natural products, as well as a two-step total synthesis

  位点选择性C(sp 3 )–H氧化在有机合成和药物发现中具有重要意义。游离羧酸的γ-C(sp 3 )–H内酯化提供了从丰富且廉价的羧酸制备具有生物学重要意义的内酯支架的最直接的方法；然而，具有广泛底物范围的这种转化的多功能催化剂仍然难以捉摸。在此，我们报道了一种简单但广泛适用且可扩展的游离脂肪酸γ-内酯化反应，该反应由铜催化剂与廉价的Selectflu作为氧化剂相结合实现。该内酯化反应表现出与叔键、苄基键、烯丙基键、亚甲基键和伯键 γ-C-H 键的相容性，可生成多种结构多样的内酯，例如螺内酯、稠合内酯和桥连内酯。值得注意的是，观察到环烷羧酸和环烷乙酸的独特γ-亚甲基C-H内酯化，得到稠合或桥联的γ-内酯，这是其他方法难以获得的。仅当存在叔δ-C-H键时，才利于δ-C-H内酯化。该方法的合成效用通过氨基酸、药物分子和天然产物的后期功能化以及(异)薄荷内酯的两步全合成（迄今为止报道的最短合成）得到证明。
• New Optically Active 4,4-Dialkyl-γ-lactones as Chiral Dopants for Ferroelectric Liquid Crystals
  作者：Tetsuya Ikemoto、Keiichi Sakashita、Yoshitaka Kageyama、Fumiko Terada、Yuriko Nakaoka、Kiyoshi Ichimura、Kenji Mori

  DOI：10.1246/cl.1992.567

  日期：1992.4

  (S)-2-(4′-n-Decyloxybiphenyl-4-carboxy)-4,4-dialkyl-γ-butyrolactones were synthesized and shown to be good chiral dopants for ferroelectric liquid crystals.

  (S)-2-(4'-n-Decyloxybiphenyl-4-carboxy)-4,4-di烷基-γ-丁内酯被合成并被证明是铁电液晶的良好手性掺杂剂。
• Enantioselective synthesis of α-hydroxy γ-butyrolactones from an ephedrine-derived morpholine-dione
  作者：Sunil V Pansare、Bidhan A Shinkre、Annyt Bhattacharyya

  DOI：10.1016/s0040-4020(02)01151-1

  日期：2002.10

  An ephedrine-derived morpholine dione is employed in the enantioselective synthesis of (S)-alpha-hydroxy- gamma,gamma-dimethyl-gamma-butyrolactone and (S)-alpha-hydroxy gamma-butyrolactone. A one-pot alkylation/allylation protocol for the stereoselective conversion of the dione to 2-alkyl-2-allyl morpholinones, key intermediates for alpha-alkyl-alpha-hydroxy-gamma-butyrolactones, is described. (C) 2002 Elsevier Science Ltd. All rights reserved.