(R)-4-benzyloxy-dihydro-2(3H)-furanone | 114784-20-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-4-benzyloxy-dihydro-2(3H)-furanone
• 英文别名: (4R)-4-phenylmethoxyoxolan-2-one
• CAS: 114784-20-2
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: BXCNEWJZGSAVED-SNVBAGLBSA-N

物化性质

• 沸点：
  347.8±35.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-4-benzyloxy-dihydro-2(3H)-furanone 在 正丁基锂 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (E)-(R)-2-Benzyloxy-docos-4-en-1-ol
  参考文献：
  名称：

  Structure determination and synthesis of a new cerebroside isolated from the traditional Chinese medicine Typhonium giganteum Engl.

  摘要：

  A new cerebroside with C18-4,8-sphingadienine as the long chain base has been isolated from the traditional Chinese medicine Typhonium giganteum Enal., and its structure was determined by 2D NMR and MS methods. It was then synthesized using D-xylose and ascorbic acid as the chiral starting materials. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00583-x
• 作为产物：
  描述：

  2-Phenylmethoxyethyl 2-diazoacetate 在 Rh₂[5S-MEPY]4 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-4-benzyloxy-dihydrofuran-2(3H)-one 、 (R)-4-benzyloxy-dihydro-2(3H)-furanone
  参考文献：
  名称：

  Asymmetric synthesis of lactones with high enantioselectivity by intramolecular carbon-hydrogen insertion reactions of alkyl diazoacetates catalyzed by chiral rhodium(II) carboxamides

  摘要：

  DOI：

  10.1021/ja00023a077

文献信息

• Beta-substituted-gamma-butyrolactones and a process for preparation thereof
  申请人：Uh, Hong-Sun

  公开号：EP1398312A1

  公开（公告）日：2004-03-17

  The present invention is related to a process for the preparation of (S)- or (R)-β-substituted-γ-butyrolactones or a racemic mixture thereof. β-substituted-γ-succinic anhydrides are converted by zinc borohydride in a compatible solvent selected from tetrahydrofuran, methylene chloride, and ethyl acetate to the corresponding β-substituted-γ-butyrolactones. The β-substituted-γ-butyrolactones obtainable in chrystallin form are useful in the production of pharmaceuticals, agrochemicals, flavors and fragrances. Also disclosed are novel β-substituted-γ-butyrolactones.

  本发明涉及一种制备(S)-或(R)-β-取代-γ-丁内酯或其混合物的过程。将β-取代-γ-琥珀酸酐通过锌硼氢化物在四氢呋喃、二氯甲烷和乙酸乙酯中选择的相容溶剂中转化为相应的β-取代-γ-丁内酯。获得的β-取代-γ-丁内酯晶体形式有用于制药、农药、香料和香精的生产。还公开了新型β-取代-γ-丁内酯。
• Bifunctional TEMPO-electrocatalysts enabled enantioselective oxidative lactonization of 1,4-diols
  作者：Pei-Sen Gao、Chang-Wang Pan、Cheng Liu、Wen-Tong Chen

  DOI：10.1016/j.mcat.2023.113663

  日期：2024.1

  resolution of racemic 1,4-diols, affording diverse chiral 1,4-diols and γ-lactones with good or excellent chemo-, regio, and enantioselectivity. We also show that this cooperative Cu/TEMPO-BOX catalytic strategy is applicable to the electro-oxidative kinetic resolution of 1,2- and 1,3-amino alcohols. This work demonstrates the potential of bifunctional electrocatalysis for asymmetric synthetic methods and

  不对称电催化有望为获得对映体富集分子提供独特的途径，而这些分子很难通过更传统的方法获得，但开发能够进行高度对映选择性转化的高效电催化剂仍然难以实现。为了实现这一令人羡慕的目标，需要能够介导氧化还原和提供高立体控制的双功能电催化剂。在这里，我们公开了一种新型 TEMPO-BOX 连接的铜电催化剂，能够氧化动力学拆分外消旋 1,4-二醇，提供具有良好或优异的化学选择性、区域选择性和对映选择性的多种手性 1,4-二醇和 γ-内酯。我们还表明，这种协同 Cu/TEMPO-BOX 催化策略适用于 1,2- 和 1,3- 氨基醇的电氧化动力学拆分。这项工作展示了双功能电催化在不对称合成方法中的潜力，我们预计它将刺激新型混合电催化剂的开发，以实现新颖的不对称电催化方法。
• Nitrile Biotransformations for the Synthesis of Highly Enantioenriched β-Hydroxy and β-Amino Acid and Amide Derivatives: A General and Simple but Powerful and Efficient Benzyl Protection Strategy To Increase Enantioselectivity of the Amidase
  作者：Da-You Ma、De-Xian Wang、Jie Pan、Zhi-Tang Huang、Mei-Xiang Wang

  DOI：10.1021/jo800074k

  日期：2008.6.1

  Biotransformations of a number of racemic beta-hydroxy and beta-amino nitrile derivatives were studied using Rhodococcus erythropolis AJ270, the nitrile hydratase and amidase-containing microbial whole cell catalyst, under very mild conditions. The overall enantioselectivity of nitrile biotransformations was governed predominantly by the amidase whose enantioselectivity was switched on remarkably by an O- and a N-benzyl protection group of the Substrates. While biotransformations of beta-hydroxy and beta-amino alkanenitriles gave low yields of amide and acid products of very low enantiomeric purity, introduction of a simple benzyl protection group on the beta-hydroxy and beta-amino of nitrile substrates led to the formation of highly enantioenriched beta-benzyloxy and beta-benzylamino amides and acids in almost quantitative yield. The easy protection and deprotection operations, high chemical yield, and excellent enantioselectivity render the nitrile biotransformation a useful protocol in the synthesis of enantiopure beta-hydroxy and beta-amino acids.
• Studies on the syntheses of the aplysiatoxins: Synthesis of a selectively-protected form of the C27 – C30 (dihydroxybutanoate) moiety of oscillatoxin A
  作者：Robert D. Walkup、Raymond T. Cunningham

  DOI：10.1016/s0040-4039(01)83850-8

  日期：1987.1
• WALKUP, ROBERT D.;CUNNINGHAM, RAYMOND T., TETRAHEDRON LETT., 28,(1987) N 35, 4019-4022
  作者：WALKUP, ROBERT D.、CUNNINGHAM, RAYMOND T.

  DOI：——

  日期：——