dodecyl β-D-fructofuranoside | 161906-73-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: dodecyl β-D-fructofuranoside
• 英文别名: (2R,3S,4S,5R)-2-dodecoxy-2,5-bis(hydroxymethyl)oxolane-3,4-diol
• CAS: 161906-73-6
• 化学式: C₁₈H₃₆O₆
• 分子量: 348.48
• InChiKey: CVKXTWAOBFFAQO-ZJPYXAASSA-N

物化性质

• 沸点：
  511.6±50.0 °C(predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-硝基苯甲酰氯 、 dodecyl β-D-fructofuranoside 在 吡啶 作用下， 以88%的产率得到
  参考文献：
  名称：

  Decyl and dodecyl β-d-fructofuranosides

  摘要：

  Decyl and dodecyl beta-D-fructofuranosides are formed from D-fructose and catalysed by boron trifluoride alcoholates, in admixture with the corresponding alpha-D anomers and beta-D-pyranosides. These were separated by chromatography and each of the products was fully characterized by NMR spectroscopy and as tetrakis(p-nitrobenzoates). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00308-5
• 作为产物：
  描述：

  果糖 、 十二烷醇 在 silica-alumina cracking catalyst HA-HPV 作用下， 70.0 ℃ 、2.0 kPa 条件下， 反应 24.0h， 生成 Dodecyl β-D-fructopyranoside 、 dodecyl β-D-fructofuranoside 、 dodecyl α-D-fructofuranoside
  参考文献：
  名称：

  Synthesis of Alkyl Fructosides Using Solid Acid Catalysts. Part I: Silica-Alumina Cracking Catalysts

  摘要：

  Silica-alumina cracking catalysts and acid clays efficiently catalyze the 2-O-alkylation of D-fructose with long chain alcohols. Under the conditions applied virtually no degradation of fructose is observed. L-Sorbose and the aldopentoses also undergo silica-alumina-catalyzed alkylation. The rate of conversion is related to the solubility of the monosaccharide and the stability of the intermediate oxocarbenium ion. Best results in fructose alkylation are obtained by applying a recirculation method with butyl fructoside as soluble intermediate.

  DOI：

  10.1080/07328309608005657

文献信息

• Mcm-41 Materials as Catalysts for the Synthesis of Alkyl Fructosides
  作者：A.M. van der Heijden、F. van Rantwijk、H. van Bekkum

  DOI：10.1080/07328309908543987

  日期：1999.1.1

  derivatives of fructose has lagged because no efficient synthesis was available. We have found that mesoporous materials of the MCM-41 type are active and selective catalysts for the alkylation of fructose. Quantitative yields were obtained in the reaction of fructose with lower alcohols, up to C4. For long chain alcohols yields were moderate but the alkyl fructopyranosides could be easily purified. The other

  糖的烷基化结合了两个主要可再生类别的基本特征，即。甘油三酸酯和碳水化合物，同时导致生物友好型表面活性剂和乳化剂。果糖的烷基化衍生物的开发滞后，因为没有有效的合成方法。我们发现MCM-41型中孔材料是果糖烷基化的活性和选择性催化剂。在果糖与低至C4的低级醇反应中获得定量收率。对于长链醇，产率中等，但是烷基果糖吡喃糖苷可以容易地纯化。其他异构体可以通过色谱法分离。
• Synthesis of Alkyl Fructosides Using Solid Acid Catalysts. Part I: Silica-Alumina Cracking Catalysts
  作者：A. T.J.W. de Goede、M. P.J. van Deurzen、I. G. van der Leij、A. M. van der Heijden、J. M.A. Baas、F. van Rantwijk、H. van Bekkum

  DOI：10.1080/07328309608005657

  日期：1996.4

  Silica-alumina cracking catalysts and acid clays efficiently catalyze the 2-O-alkylation of D-fructose with long chain alcohols. Under the conditions applied virtually no degradation of fructose is observed. L-Sorbose and the aldopentoses also undergo silica-alumina-catalyzed alkylation. The rate of conversion is related to the solubility of the monosaccharide and the stability of the intermediate oxocarbenium ion. Best results in fructose alkylation are obtained by applying a recirculation method with butyl fructoside as soluble intermediate.
• Decyl and dodecyl β-d-fructofuranosides
  作者：Henk Regeling、Binne Zwanenburg、Gordon J.F. Chittenden

  DOI：10.1016/s0008-6215(98)00308-5

  日期：1998.12

  Decyl and dodecyl beta-D-fructofuranosides are formed from D-fructose and catalysed by boron trifluoride alcoholates, in admixture with the corresponding alpha-D anomers and beta-D-pyranosides. These were separated by chromatography and each of the products was fully characterized by NMR spectroscopy and as tetrakis(p-nitrobenzoates). (C) 1998 Elsevier Science Ltd. All rights reserved.