1,4:3,6-dianhydro-2,5-di-O-benzyl-D-glucitol | 6338-36-9

• 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: 1,4:3,6-dianhydro-2,5-di-O-benzyl-D-glucitol
• 英文别名: di-O-benzyl-1,4;3,6-dianhydro-D-glucitol；Di-O-benzyl-1,4;3,6-dianhydro-D-glucit；isosorbide 2,5-dibenzyl ether；(3S,3aR,6R,6aR)-3,6-bis(phenylmethoxy)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan
• CAS: 6338-36-9
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: QWKHGLDNMRMYFF-IYWMVGAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  溴甲苯 在 sodium hydroxide 、 15-冠醚-5 作用下， 以 N,N-二甲基乙酰胺 、 水 、 甲苯 为溶剂， 反应 15.0h， 以46%的产率得到1,4:3,6-dianhydro-2,5-di-O-benzyl-D-glucitol
  参考文献：
  名称：

  Ethers of bisanhydrohexitols

  摘要：

  本发明揭示了一种合成无水糖醚的新方法，例如异山梨醇、异甘醇和异戊醇。双环氧醚对于制造热固性环氧醚中替代双酚A非常有用。无水糖醚来源于可再生资源，不具有外源性雌激素作用。较高的烷基和芳基糖醚是稳定的高沸点油，对于PVC等材料是良好的增塑剂。

  公开号：

  US20080021209A1

文献信息

• Chiral ionic liquids derived from isosorbide: synthesis, properties and applications in asymmetric synthesis
  作者：Olivier Nguyen Van Buu、Audrey Aupoix、Nhung Doan Thi Hong、Giang Vo-Thanh

  DOI：10.1039/b902956g

  日期：——

  A novel class of chiral ammonium and imidazolium-based ionic liquids has been designed and synthesized using isosorbide as a biorenewable substrate. These chiral ionic liquids were found to catalyze the aza Diels–Alder reaction to give good yields and moderate diastereoselectivitives.

  以异山梨醇为生物可再生底物，设计并合成了一类新型手性铵和咪唑离子液体。研究发现，这些手性离子液体可催化偶氮 Diels-Alder 反应，产生良好的产率和适度的非对映选择性。
• Selective alkylations of 1,4:3,6-dianhydro-d-glucitol (isosorbide)
  作者：D. Abenhaïm、A. Loupy、L. Munnier、R. Tamion、F. Marsais、G. Quéguiner

  DOI：10.1016/0008-6215(94)84022-9

  日期：1994.8

  Each of the two hydroxyl groups of isosorbide can be alkylated selectively, either by direct alkylation with benzyl chloride or allyl bromide according to the reaction conditions, or by a three-step procedure involving selective monoacetylation, alkylation with four different reagents, and finally deacetylation. Monobutyl and monomethyl derivatives from isosorbide are also described.

  摘要异山梨醇的两个羟基均可根据反应条件，通过与苄基氯或烯丙基溴直接烷基化，或通过涉及选择性单乙酰化，用四种不同试剂烷基化，最后脱乙酰基的三步法进行选择性烷基化。还描述了异山梨醇的单丁基和单甲基衍生物。
• Esters of anhydrosugar alcohols as plasticizers
  申请人：East Anthony

  公开号：US20070282042A1

  公开（公告）日：2007-12-06

  The invention consists of esters of anhydrosugar alcohols useful as plasticizers for polymeric compounds. Specifically, esters are formed of bis-anhydrohexitols, such as isosorbide, isomannide and isosiditide, and used as substitutes for the phthalate-based plasticizers in common use. The bis-anhydrohexitols are preferably produced from biological sources.

  该发明涉及一种用作高分子化合物增塑剂的无水糖醇酯。具体而言，该酯是由双无水己糖醇（例如异山梨醇、异甘露醇和异山梨糖醇）形成的，并用作常用邻苯二甲酸酯类增塑剂的替代品。最好从生物来源中生产双无水己糖醇。
• The Acetolysis of Some Carbohydrate Benzyl Ethers
  作者：R. Allerton、Hewitt G. Fletcher

  DOI：10.1021/ja01636a011

  日期：1954.4
• Synthesis of novel chiral imidazolium-based ionic liquids derived from isosorbide and their applications in asymmetric aza Diels–Alder reaction
  作者：Olivier Nguyen Van Buu、Audrey Aupoix、Giang Vo-Thanh

  DOI：10.1016/j.tet.2009.01.055

  日期：2009.3

  A novel family of chiral imidazolium-based ionic liquids containing a Chiral moiety and a free hydroxyl function has been designed and synthesized using isosorbide as a biorenewable substrate. These chiral ionic liquids were found to catalyze the aza Diels-Alder reaction to give good yields and moderate diastereoselectivities. Chiral ionic liquids are recycled while their efficiency is preserved. (C) 2009 Elsevier Ltd. All rights reserved.