3,3-二甲基-2-亚甲基-2,3-二氢苯并呋喃 | 53990-79-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3,3-二甲基-2-亚甲基-2,3-二氢苯并呋喃
• 英文名称: 1',2-anhydro-1-O-α-D-fructopyranosyl-(1C)-β-D-fructofuranose-(E3)
• 英文别名: β-D-fructofuranose α-D-fructopyranose 1,2':2,1'-dianhydride；β-D-Fruf-1,2':2,1'-α-D-Frup；(1S,2S,3R,5R,8R,11R,12R,13S)-3-(hydroxymethyl)-4,6,9,14-tetraoxadispiro[4.2.58.25]pentadecane-1,2,11,12,13-pentol
• CAS: 53990-79-7
• 化学式: C₁₂H₂₀O₁₀
• 分子量: 324.285
• InChiKey: NMQBLDSHULSXOV-TWOHWVPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  158
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  在 palladium on activated charcoal 甲酸 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 以99%的产率得到3,3-二甲基-2-亚甲基-2,3-二氢苯并呋喃
  参考文献：
  名称：

  Spacer-Mediated Synthesis of Bis-spiroketal Disaccharides: Nonsymmetrical Furanose-Pyranose Difructose Dianhydrides

  摘要：

  d-果糖的二聚反应形成三环双螺旋酮体系的立体化学结果可以通过在反应单元间插入二甲苯模板来调节。螺旋环化因此成为一种分子内过程，所需的构象空间取决于连接链的性质。该方法通过对商用焦糖中存在的两种非对称二-d-果糖二醇酯的立体选择性合成进行了说明。

  DOI：

  10.1055/s-2007-991055

文献信息

• The Dehydration of Ketohexoses into 5-Chloromethyl-2-furaldehyde. The Isolation of Diketohexose Dianhydrides
  作者：Kazuhiko Hamada、Hiroshi Yoshihara、Gohfu Suzukamo、Osamu Hiroaki

  DOI：10.1246/bcsj.57.307

  日期：1984.1

  The isolation of diketohexose dianhydrides, produced during the dehydration of d(−)-fructose and l(−)-sorbose with concentrated hydrochloric acid, in a mixture containing water, an organic solvent and a catalytic amount of a surface-active agent is described.

  描述了在含有水、有机溶剂和催化量的表面活性剂的混合物中，用浓盐酸对 d(-)-果糖和 l(-)-山梨糖进行脱水时产生的二酮六糖二酐的分离过程。
• Carbon Dioxide as a Traceless Caramelization Promotor: Preparation of Prebiotic Difructose Dianhydrides (DFAs)-Enriched Caramels from <scp>d</scp>-Fructose
  作者：Maïté Audemar、Loyda Atencio-Genes、Carmen Ortiz Mellet、François Jérôme、José Manuel Garcia Fernandez、Karine De Oliveira Vigier

  DOI：10.1021/acs.jafc.7b01601

  日期：2017.8.2

  glycosylated derivatives (glycosyl-DFAs), a family of prebiotic oligosaccharides. Under optimized conditions, up to 70% of the active DFA species were obtained from a highly concentrated solution of fructose, avoiding the filtration step and contamination risk associated with the current procedures that employ heterogeneous catalysis with acid ion-exchange resins. The optimized CO2-promoted preparation of DFA-enriched

  由二氧化碳生成的d-果糖浓缩溶液被二氧化碳活化，可诱导形成二果糖二酐（DFA）及其糖基化衍生物（糖基-DFA），这是一种益生元寡糖家族。在优化的条件下，从果糖的高浓度溶液中最多可获得70％的活性DFA物质，从而避免了过滤步骤和与采用酸离子交换树脂进行多相催化的现有程序相关的污染风险。本文所述的优化的由CO 2促进的富含DFA的焦糖制剂的规模已成功扩大到150 kg d。-果糖用于营养研究，表明该过程的大规模实施是可能的。
• Stereoselective synthesis of nonsymmetrical difructose dianhydrides from xylylene-tethered d-fructose precursors
  作者：Farida Louis、M. Isabel García-Moreno、Patricia Balbuena、Carmen Ortiz Mellet、José M. García Fernández

  DOI：10.1016/j.tet.2008.01.054

  日期：2008.3

  Nonsymmetrical furanose-pyranose difructose dianhydrides (DFAs), a class of cyclic disaccharides present in foodstuffs, have been prepared in high yield by connecting the reacting monosaccharide moieties through a xylylene bridge prior to triflic acid-promoted bis-spiroketalization. The reaction can then proceed either intra- or intermolecularly, both the regio- and the stereoselectivity being strongly dependent on the spacer length. Noteworthy, the longer m- and p-xylylene positional isomers led to the thermodynamic alpha-D-fructofuranose beta-D-fructopyranose 1,2':2,1'-dyanhydride 1, the major DFA in commercial caramel, in a stereoselective manner. The shorter o-xylylene tether afforded preferentially the elusive contra-thermodynamic beta-D-fructofuranose alpha-D-fructopyranose diastereomer 2, a trace constituent of caramel. The results have been rationalized in terms of stereoelectronic and conformational properties and offer new perspectives for the preparation of pure DFA standards for analytical and nutritional studies. (C) 2008 Elsevier Ltd. All rights reserved.
• Action of Heat on D-Fructose. II.¹ Structure of Diheterolevulosan II
  作者：M. L. Wolfrom、W. W. Binkley、W. L. Shilling、H. W. Hilton

  DOI：10.1021/ja01152a001

  日期：1951.8
• Action of Heat on D-Fructose. Isolation of Diheterolevulosan and a New Di-D-fructose Dianhydride
  作者：M. L. Wolfrom、Mary Grace Blair

  DOI：10.1021/ja01187a027

  日期：1948.7