5-(hydroxymethyl)furan-2-carbaldehyde-13C | 1220910-93-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(hydroxymethyl)furan-2-carbaldehyde-13C
• CAS: 1220910-93-9
• 化学式: C₆H₆O₃
• 分子量: 127.101
• InChiKey: NOEGNKMFWQHSLB-LBPDFUHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.58
• 重原子数：
  9.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  50.44
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  ¹³C-C1-glucopyranose 在 1-methyl-3-(propyl-3-sulfonic acid)imidazole chloride salt 作用下， 以 氘代二甲亚砜 为溶剂， 反应 4.0h， 生成 5-(hydroxymethyl)furan-2-carbaldehyde-13C
  参考文献：
  名称：

  Mechanism of 1-(1-propylsulfonic)-3-methylimidazolium chloride catalyzed transformation of d-glucose to 5-hydroxymethylfurfural in DMSO: an NMR study

  摘要：

  The conversion of D-glucose to 5-hydroxymethylfurfural (HMF) in the presence of 5.48 mol % 1-(1-propylsulfonic)-3-methylimidazolium chloride acidic ionic liquid catalyst in DMSO at 150 degrees C was studied using H-1, C-13 NMR, and visible spectroscopy. The HMF yield rapidly increases in the first 100 min of reaction, however yield drops beyond 100 min and levels off to a maximum yield of about 15.7% around 600 min. The visible spectroscopy study of the reaction mixture suggests that rate of HMF formation slows down after 100 min due to increase in the rate of humin formation after first 100 min. A mechanism has been proposed and key intermediates in the pathway could be identified by studying the C-13 NMR spectra of acidic ionic liquid catalyzed transformations of C-1 and C-2 C-13 labeled D-glucose under identical conditions. The proposed mechanism involves the isomerization of D-glucose to D-fructose via the complexation of the open chain sugar with the imidazolium cation of the acidic ionic liquid catalyst. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.01.009

文献信息

• Mechanism of Brønsted Acid-Catalyzed Glucose Dehydration
  作者：Liu Yang、George Tsilomelekis、Stavros Caratzoulas、Dionisios G. Vlachos

  DOI：10.1002/cssc.201403264

  日期：2015.4.24

  the rate‐limiting step is the first dehydration of protonated glucose and that the majority of glucose is consumed through the HMF intermediate. We introduce a combination of 1) automatic mechanism generation with isotopic tracing experiments and 2) elementary reaction flux analysis of important paths with NMR spectroscopy and kinetic experiments to assess mechanisms. We find that the excess formic acid

  我们介绍了第一个基于DFT的微动力学模型，用于布朗斯台德酸催化的葡萄糖向葡萄糖转化为5-羟甲基糠醛（HMF），乙酰丙酸（LA）和甲酸（FA）的转化，并主要在低转化率下进行动力学和同位素示踪NMR光谱分析。我们揭示葡萄糖通过循环路径脱水。我们的建模结果与动力学数据非常吻合，表明限速步骤是质子化葡萄糖的首次脱水，并且大部分葡萄糖是通过HMF中间体消耗的。我们介绍了1）结合同位素示踪实验自动生成机理，以及2）利用NMR光谱学和动力学实验对重要路径进行基本反应通量分析以评估机理的方法。我们发现过量的甲酸，