1,2-二(呋喃-3-基)-2-羟基乙酮 | 862898-07-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,2-二(呋喃-3-基)-2-羟基乙酮
• 英文名称: 1,2-di(furan-3-yl)-2-hydroxyethanone
• 英文别名: furoin；1,2-Bis(furan-3-yl)-2-hydroxyethanone
• CAS: 862898-07-5
• 化学式: C₁₀H₈O₄
• 分子量: 192.171
• InChiKey: MTSVJIHGNXJKLC-UHFFFAOYSA-N

物化性质

• 沸点：
  320.9±32.0 °C(Predicted)
• 密度：
  1.320±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-二(呋喃-3-基)-2-羟基乙酮 在 sodium hypochlorite 作用下， 反应 0.08h， 以65%的产率得到3-糠酸
  参考文献：
  名称：

  α-取代羰基化合物在水介质中微波辅助氧化成羧酸

  摘要：

  摘要 含有吸电子取代基的羰基化合物可在不添加有机溶剂的情况下使用微波被次氯酸钠水溶液有效氧化。

  DOI：

  10.1080/00397919708004184
• 作为产物：
  描述：

  3-糠醛 在 sodium hydroxide 、 盐酸硫胺 作用下， 以 乙醇 、 水 为溶剂， 反应 48.0h， 以110 mg的产率得到1,2-二(呋喃-3-基)-2-羟基乙酮
  参考文献：
  名称：

  Stereoselective synthesis of novel benzoins catalysed by benzaldehyde lyase in a gel-stabilised two-phase system

  摘要：

  Asymmetric benzoin condensation was performed using recombinant benzaldehyde lyase (BAL) from Pseudomonas fluorescens Biovar I. To enable the conversion of hydrophobic substrates, the enzyme was entrapped in polyvinyl alcohol and suspended in hexane. Compared to the reported application of the biocatalyst in an aqueous phase containing 20% DMSO, the productivity of the resulting gel-stabilised two-phase system was 3-fold better. The entrapment process had an efficiency of > 90%, no enzyme or cofactor was lost during reaction or storage. The entrapped enzyme was stable in hexane for 1 week at 4 degrees C and more than 1 month at -20 degrees C. Without preceding optimisation the novel benzoins (R)-1,2-di(3-furanyl)-2-hydroxyethanone, (R)-2-hydroxy-1,2-di(3-thienyl) ethanone, (R)-1,2-di(4-ethoxyphenyl)-2-hydroxyethanone, (R)-1,2-di(3-ethoxyphenyl)-2-hydroxyethanone, (R)-2-hydroxy-1,2-di(3-tolyl)ethanone, and (R)-1,2-di(benzofuran-2-yl)-2-hydroxyethanone were prepared with yields up to 31.8% and enantiomeric excess > 99%. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.05.082

文献信息

• Base-Promoted Three-Component Cascade Reaction of α-Hydroxy Ketones, Malonodinitrile, and Alcohols: Direct Access to Tetrasubstituted N<i>H</i>-Pyrroles
  作者：Hongjian Liu、Chaorong Qi、Lu Wang、Yanhui Guo、Dan Li、Huanfeng Jiang

  DOI：10.1021/acs.joc.1c00882

  日期：2021.7.16

  malonodinitrile, and alcohols has been developed, providing a direct and efficient route to a range of structurally diverse and synthetically useful 2-alkyloxy-1H-pyrrole-3-carbonitrile derivatives. The reaction involved three different bond (C–C, C–O, and C–N) formations in a single step, and its regioselectivity was depended on the structure of the α-hydroxy ketones employed. The use of easily available

  已经开发了 α-羟基酮、丙二腈和醇的碱促进三组分级联反应，为一系列结构多样且合成有用的 2-烷氧基-1 H-吡咯-3-腈提供了直接有效的途径衍生品。该反应在一个步骤中涉及三种不同的键（C-C、C-O 和 C-N）的形成，其区域选择性取决于所使用的 α-羟基酮的结构。使用容易获得的起始材料、广泛的底物范围、良好的官能团耐受性、操作简单和高原子经济性是新方法的吸引人的特点。
• Enantioselective monoreduction of different 1,2-diaryl-1,2-diketones catalysed by lyophilised whole cells from Pichia glucozyma
  作者：Pilar Hoyos、Giacomo Sansottera、María Fernández、Francesco Molinari、José Vicente Sinisterra、Andrés R. Alcántara

  DOI：10.1016/j.tet.2008.06.019

  日期：2008.8

  In this work we have studied the monoreduction of different 1,2-diaryl-ethanediones (benzils, 1) with lyophilised whole cells from Pichia glucozyma CBS 5766, using the diphenyl compound (benzil, 1a) as model substrate, and extended the enantioselective reduction to structurally different symmetric benzils for producing enantiomerically pure or enriched benzoins (α-hydroxyketones 2) in high yields and

  在这项工作中，我们研究了以二苯基化合物（苯并1a）为模型底物，用葡糖毕赤酵母CBS 5766的冻干全细胞对不同的1,2-二芳基-乙二酮（苯并1）进行单还原，并扩展了对映选择性还原到结构上不同的对称苯，以生产对映体纯的或富集的苯偶姻（α-羟基酮2），收率高，反应时间短。为了研究该生物催化剂的区域选择性和立体选择性，我们研究了由不同芳基部分形成的二芳基二酮的还原，以获得对称和不对称的交叉安息香。该方法是在非常温和的反应条件下（含少量DMSO的水介质溶解底物，T = 28°C）进行的，因此与其他报道的获得同手性苯偶姻的方法相比，它是一种绿色的替代方法。
• Daoud; Mohammad; Fattah, Journal of the Indian Chemical Society, 1990, vol. 67, # 11, p. 869 - 870
  作者：Daoud、Mohammad、Fattah

  DOI：——

  日期：——
• Microwave-Assisted Oxidation of α-Substituted Carbonyl Compounds to Carboxylic Acids in Aqueous Media
  作者：D. T. C. Yang、C. J. Zhang、B. C. Haynie、P. P. Fu、G. W. Kabalka

  DOI：10.1080/00397919708004184

  日期：1997.9

  Abstract Carbonyl compounds containing electron-withdrawing substituents are efficiently oxidized by aqueous sodium hypochlorite in the absence of added organic solvents using microwaves.

  摘要 含有吸电子取代基的羰基化合物可在不添加有机溶剂的情况下使用微波被次氯酸钠水溶液有效氧化。
• Stereoselective synthesis of novel benzoins catalysed by benzaldehyde lyase in a gel-stabilised two-phase system
  作者：Tanja Hischer、Dörte Gocke、María Fernández、Pilar Hoyos、Andrés R. Alcántara、José V. Sinisterra、Winfried Hartmeier、Marion B. Ansorge-Schumacher

  DOI：10.1016/j.tet.2005.05.082

  日期：2005.8

  Asymmetric benzoin condensation was performed using recombinant benzaldehyde lyase (BAL) from Pseudomonas fluorescens Biovar I. To enable the conversion of hydrophobic substrates, the enzyme was entrapped in polyvinyl alcohol and suspended in hexane. Compared to the reported application of the biocatalyst in an aqueous phase containing 20% DMSO, the productivity of the resulting gel-stabilised two-phase system was 3-fold better. The entrapment process had an efficiency of > 90%, no enzyme or cofactor was lost during reaction or storage. The entrapped enzyme was stable in hexane for 1 week at 4 degrees C and more than 1 month at -20 degrees C. Without preceding optimisation the novel benzoins (R)-1,2-di(3-furanyl)-2-hydroxyethanone, (R)-2-hydroxy-1,2-di(3-thienyl) ethanone, (R)-1,2-di(4-ethoxyphenyl)-2-hydroxyethanone, (R)-1,2-di(3-ethoxyphenyl)-2-hydroxyethanone, (R)-2-hydroxy-1,2-di(3-tolyl)ethanone, and (R)-1,2-di(benzofuran-2-yl)-2-hydroxyethanone were prepared with yields up to 31.8% and enantiomeric excess > 99%. (c) 2005 Elsevier Ltd. All rights reserved.