isosorbide 5-O-propanoate | 125411-44-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: isosorbide 5-O-propanoate
• 英文别名: 5-propionyl isosorbide；[(3S,3aR,6R,6aR)-3-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl] propanoate
• CAS: 125411-44-1
• 化学式: C₉H₁₄O₅
• 分子量: 202.207
• InChiKey: AYFIIPKOTWMNAN-HIORRCEOSA-N

物化性质

• 沸点：
  333.9±42.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  丙酰氯 、 异山梨醇 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以27%的产率得到isosorbide 5-O-propanoate
  参考文献：
  名称：

  衍生自异山梨醇的挥发性短链两亲物：酯与醚的 水溶性质

  摘要：

  合成了两个系列的不同于游离羟基位置的短链异山梨醇单链烷酸酯，并评估为挥发性非离子水溶助长剂，也称为“溶剂表面活性剂”。评价了它们的水溶解度，增溶效率和挥发性，并与相应的5- O-烷基异山梨醇酯进行了比较。无论酰化位置（5- O-或2- O-）如何，异山梨醇单链烷酸酯的水溶性差，对于长于四个碳原子的酰基链而言，而5- O-烷基异山梨醇酯可与水完全混溶直至戊基链，这似乎表明对于这些类型的分子，醚键比酯键具有更大的亲水性。较短的异山梨醇单链烷酸酯可与水完全混溶，而丁酸酯在疏水性化合物的水溶液增溶方面特别有效。另外，所有的水溶助长剂都具有一定的挥发性，尽管不是挥发性有机化合物，并且与它们的醚同系物相反，异山梨醇链烷酸酯很容易在碱性介质中水解，这表明其具有良好的生物降解性。

  DOI：

  10.1039/c3ra40205c

文献信息

• Regioselektive Acylierung von 1,4:3,6-Dianhydro-D-glucit
  作者：Peter Stoss、Peter Merrath、Günther Schlüter

  DOI：10.1055/s-1987-27878

  日期：——

  Regioselective Acylation of 1,4:3,6-Dianhydro-D-glucitol Acylation of 1,4:3,6-dianhydro-D-glucitol with anhydrides in the presence of heavy metal salts affords 5-endo-acylates with high regioselectivity, without detectable amounts of the isomeric 2-acylates. Acyl group migration occurs with preference for the 2-exo-position, on heating an acylation mixture, which contains varying amounts of 1,4:3,6-dianhydro-D-glucitol, 2- and 5-monoacylate and 2,5-diacylate, in the presence of reesterification catalysts and whilst distilling off the lower boiling 2-acylate.

  1,4:3,6-二脱氢-D-葡萄糖醇的区域选择性酰化 1,4:3,6-二脱氢-D-葡萄糖醇在重金属盐存在下与酸酐发生酰化反应，可生成具有高区域选择性的 5-内向酰化物，且检测不到大量异构的 2-酰化物。在有酯化催化剂存在的情况下，加热含有不同量的 1,4:3,6-二脱氢-D-葡萄糖醇、2-和 5-单乙酸酯以及 2,5-二乙酸酯的酰化混合物，同时蒸馏掉沸点较低的 2-乙酸酯，就会发生酰基迁移，优先选择 2-外位。
• Selective Esterification of 1,4:3,6-Dianhydro-D-glucitol
  作者：Živorad Čeković、Zorana Tokić

  DOI：10.1055/s-1989-27332

  日期：——

  Esterification of 1,4:3,6-dianhydro-D-glucitol (1) with carboxcylic acids in the presence of 4-dimethylaminopyridine and dicyclohexylcar- bodiimide affords 2-exo-acylates 3 with high regioselectivity, in addition to small amounts of the isomeric 5-endo-acylates 4 and 2,5-diacylates 5.

  在 4-二甲基氨基吡啶和二环己基碳二亚胺的存在下，1,4:3,6-二氢-D-葡萄糖醇（1）与羧酸发生酯化反应，除了生成少量异构的 5-内向酰化物 4 和 2,5-二酰化物 5 外，还能以高区域选择性生成 2-外向酰化物 3。
• METHOD FOR QUANTITATIVE ANALYSIS OF SUGARS, SUGAR ALCOHOLS AND RELATED DEHYDRATION PRODUCTS
  申请人：Howard Stephen

  公开号：US20130337570A1

  公开（公告）日：2013-12-19

  An improved method is provided for the quantitative analysis of mixtures including various sugars, sugar alcohols and related dehydration products, whereby these are enabled to be effectively and accurately quantitated through gas chromatography, for example, by their derivatization with a carboxylic acid, carboxylic acid anhydride or halide in the presence of a metal triflate catalyst. The method can be carried out at essentially room temperature conditions, with a sufficiently rapid and complete derivatization, even in the presence of substantial amounts of water, that the materials to be quantitated do not substantially break down or degrade and substantially completely accounted for in a derivatized form.
• [EN] IMPROVED METHOD FOR QUANTITATIVE ANALYSIS OF SUGARS, SUGAR ALCOHOLS AND RELATED DEHYDRATION PRODUCTS<br/>[FR] PROCÉDÉ AMÉLIORÉ D'ANALYSE QUANTITATIVE DE SUCRES, D'ALCOOLS DE SUCRE ET DES PRODUITS DE DÉSHYDRATATION ASSOCIÉS
  申请人：ARCHER DANIELS MIDLAND CO

  公开号：WO2012121913A2

  公开（公告）日：2012-09-13

  An improved method is provided for the quantitative analysis of mixtures including various sugars, sugar alcohols and related dehydration products, whereby these are enabled to be effectively and accurately quantitated through gas chromatography, for example, by their derivatization with a carboxylic acid, carboxylic acid anhydride or halide in the presence of a metal triflate catalyst. The method can be carried out at essentially room temperature conditions, with a sufficiently rapid and complete derivatization, even in the presence of substantial amounts of water, that the materials to be quantitated do not substantially break down or degrade and substantially completely accounted for in a derivatized form.