(3S,6S)-dimethyl hexahydrofuro[3,2-b]furan-3,6-dicarboxylate | 1309611-87-7

• 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: (3S,6S)-dimethyl hexahydrofuro[3,2-b]furan-3,6-dicarboxylate
• 英文别名: dimethyl (3S,6S)-hexahydrofuro[3,2-b]furan-3,6-dicarboxylate；dimethyl (3S,3aR,6S,6aR)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-dicarboxylate
• CAS: 1309611-87-7
• 化学式: C₁₀H₁₄O₆
• 分子量: 230.218
• InChiKey: RRHJBNGFEIUKST-RULNZFCNSA-N

物化性质

• 沸点：
  289.3±35.0 °C(Predicted)
• 密度：
  1.277±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S,6S)-dimethyl hexahydrofuro[3,2-b]furan-3,6-dicarboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以58%的产率得到((3S,3AR,6S,6AR)-六氢呋喃并[3,2-B]呋喃-3,6-二基)二甲醇
  参考文献：
  名称：

  来自可再生资源的异己酮衍生物作为手性砌块

  摘要：

  扩展族：以立体控制的方式合成了一个新的C2 / C5碳扩展的异己酸衍生物系列，具有高纯度和高收率。这些手性和刚性生物基构建基块可以广泛应用：在药物，胆甾型液晶中，以及作为高性能聚合物的构建基块。基于异戊二烯的二酸是对苯二甲酸的潜在可再生替代品。

  DOI：

  10.1002/cssc.201100076
• 作为产物：
  描述：

  1,4:3,6-dianhydro-D-mannitol 在 吡啶 、 盐酸 、 18-冠醚-6 、 水 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 (3S,6S)-dimethyl hexahydrofuro[3,2-b]furan-3,6-dicarboxylate
  参考文献：
  名称：

  来自可再生资源的异己酮衍生物作为手性砌块

  摘要：

  扩展族：以立体控制的方式合成了一个新的C2 / C5碳扩展的异己酸衍生物系列，具有高纯度和高收率。这些手性和刚性生物基构建基块可以广泛应用：在药物，胆甾型液晶中，以及作为高性能聚合物的构建基块。基于异戊二烯的二酸是对苯二甲酸的潜在可再生替代品。

  DOI：

  10.1002/cssc.201100076

文献信息

• [EN] NEW BIOBASED CHIRAL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS CHIRAUX À BASE BIOLOGIQUE
  申请人：STICHTING DUTCH POLYMER INST

  公开号：WO2011144353A1

  公开（公告）日：2011-11-24

  The present invention relates to a compound which has the general formula: wherein R1 and R2 are independently from one another selected from the group consisting of -OH; -CN; -COOH; -CH2NH2; -CH2OH; -(C=0)-0-Rx; -CH2NCO, and oxazoline, provided that R1 and R2 are not both -OH and wherein Rx may be a branched or unbranched C1-C22 alkyl-group. The present invention also relates to preparation methods for and uses of such compounds.

  本发明涉及一种具有通式的化合物：其中R1和R2分别独立地选自包括-OH；-CN；-COOH；-CH2NH2；-CH2OH；-(C=0)-0-Rx；-CH2NCO和噁唑啉的群体，前提是R1和R2不能同时为-OH，而Rx可能是支链或直链的C1-C22烷基基团。本发明还涉及这种化合物的制备方法和用途。
• Isohexide and Sorbitol-Derived, Enzymatically Synthesized Renewable Polyesters with Enhanced <i>T</i>_g
  作者：Liliana Gustini、Cristina Lavilla、Antxon Martínez de Ilarduya、Sebastián Muñoz-Guerra、Cor E. Koning

  DOI：10.1021/acs.biomac.6b01224

  日期：2016.10.10

  sorbitol-containing polyester lacking isohexides. The different capability of the two isohexides to boost the thermal properties confirmed the more flexible character provided by the isoidide diester derivative. Solvent-borne coatings were prepared by cross-linking the sugar-based polyester polyols with polyisocyanates. The increased rigidity of the obtained sugar-based polyester polyols led to an enhancement

  通过无溶剂的酶催化获得衍生自山梨糖醇和异己糖的糖基聚酯。来自山梨糖醇单元的侧链羟基沿聚酯主链存在，而选择两种异己糖，即异甘露糖苷和异麦苷二甲基酯单体，以将刚性引入聚酯链中。研究了通过脂肪酶催化的缩聚反应，将异甘露糖醇作为二醇掺入到异戊二烯酸二甲酯作为酰基供体中的可行性。双环单元的存在导致T g增强相对于母体含山梨糖醇的缺少异己糖的聚酯。两种异己酮提高热性能的能力不同，证实了异戊二烯二酯衍生物具有更灵活的特性。通过使基于糖的聚酯多元醇与多异氰酸酯交联来制备溶剂型涂料。所获得的糖基聚酯多元醇的刚性增加导致所得涂层的硬度提高。
• Isohexide Derivatives from Renewable Resources as Chiral Building Blocks
  作者：Jing Wu、Pieter Eduard、Shanmugam Thiyagarajan、Jacco van Haveren、Daan S. van Es、Cor E. Koning、Martin Lutz、Célia Fonseca Guerra

  DOI：10.1002/cssc.201100076

  日期：2011.5.23

  A new family of C2/C5 carbon‐extended isohexide derivatives is synthesized in a stereo‐controlled manner with high purity and good yield. These chiral and rigid biobased building blocks can be widely applied: in pharmaceuticals, cholesteric liquid crystals, and as building blocks for high‐performance polymers. The isoidide‐based diacid is a potential renewable alternative to terephthalic acid.

  扩展族：以立体控制的方式合成了一个新的C2 / C5碳扩展的异己酸衍生物系列，具有高纯度和高收率。这些手性和刚性生物基构建基块可以广泛应用：在药物，胆甾型液晶中，以及作为高性能聚合物的构建基块。基于异戊二烯的二酸是对苯二甲酸的潜在可再生替代品。
• Semicrystalline Polyesters Based on a Novel Renewable Building Block
  作者：Jing Wu、Pieter Eduard、Shanmugam Thiyagarajan、Lidia Jasinska-Walc、Artur Rozanski、Célia Fonseca Guerra、Bart A. J. Noordover、Jacco van Haveren、Daan S. van Es、Cor E. Koning

  DOI：10.1021/ma300782h

  日期：2012.6.26

  Isohexides, like e.g. isosorbide, are well-known carbohydrate-based rigid diols which are capable of dramatically increasing the glass transition temperature of polyesters. However, their relatively low reactivity has thus far hampered large-scale industrial applications in the polymer field. Recently, with the aim to increase reactivity while at the same time retain rigidity, we have developed a new isoidide dicarboxylic acid (IIDCA) by transforming the secondary hydroxyls into carboxylate functionahties. Here we report the first polymers based on IIDCA and linear alpha,omega-diols. The novel polyesters were obtained via melt polymerization and exhibited weight-average molecular weights in the range of 13 000-34 000 g/mol and polydispersities close to 2.0. NMR analyses showed that the exo-exo configuration of the isoidide dicarboxylate units was preserved during synthesis. Both differential scanning calorimetry and wide-angle X-ray diffraction analyses showed that the IIDCA polyesters are semicrystalline materials. A systematic study on structure thermal properties relations among relevant series of polyesters, such as isomeric polymers based on isoidide, revealed several interesting differences in melting and glass transition temperatures, which are thought to be related to variations in chain packing and free volume.