2,5-双[羟甲基]四氢呋喃 | 81370-89-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 中文名称: 2,5-双[羟甲基]四氢呋喃
• 中文别名: 2,5-二羟甲基四氢呋喃
• 英文名称: (-)-(2R,5R)-trans-2,5-bis(hydroxymethyl)tetrahydrofuran
• 英文别名: 2,5-anhydro-3,4-dideoxy-D-iditol；2,5-Tetrahydrofurandimethanol, ((2R,5R)-；[(2R,5R)-5-(hydroxymethyl)oxolan-2-yl]methanol
• CAS: 81370-89-0
• 化学式: C₆H₁₂O₃
• 分子量: 132.159
• InChiKey: YCZZQSFWHFBKMU-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-双[羟甲基]四氢呋喃 在 吡啶 、 potassium tert-butylate 作用下， 反应 62.0h， 生成 (6R,9R,16S,19S)-2,3,12,13-dibenzo-1,4,11,14-tetraoxa-6,9,16,19-dioxocycloeicosa-2,12-diene
  参考文献：
  名称：

  Synthesis of stereoisomeric crown ethers composed of cis- and trans-2,5-bis(hydroxymethyl)tetrahydrofuran units and their selective transport of alkali metal cations through liquid membranes

  摘要：

  DOI：

  10.1021/jo00133a038
• 作为产物：
  描述：

  (+)-(2R,5R)-trans-2,5-bis(methoxycarbonyl)tetrahydrofuran 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 12.0h， 以79%的产率得到2,5-双[羟甲基]四氢呋喃
  参考文献：
  名称：

  Synthesis of stereoisomeric crown ethers composed of cis- and trans-2,5-bis(hydroxymethyl)tetrahydrofuran units and their selective transport of alkali metal cations through liquid membranes

  摘要：

  DOI：

  10.1021/jo00133a038

文献信息

• Synthesis and Conformational Studies of Peptidomimetics Containing Furanoid Sugar Amino Acids and a Sugar Diacid
  作者：T. K. Chakraborty、S. Ghosh、S. Jayaprakash、J. A. R. P. Sharma、V. Ravikanth、P. V. Diwan、R. Nagaraj、A. C. Kunwar

  DOI：10.1021/jo000408e

  日期：2000.10.1

  Incorporation of these furanoid sugar amino acids into Leu-enkephalin replacing its Gly-Gly portion gave analogues 8-11. Detailed structural analysis of these molecules by circular dichroism (CD) and various NMR techniques in combination with constrained molecular dynamics (MD) simulations revealed that two of these analogues, 8a and 10a, have folded conformations composed of an unusual nine-membered pseudo

  合成了呋喃糖糖氨基酸（1），用作二肽等位基因，以诱导小的线性肽中有趣的转弯结构。它们属于新设计的杂合结构的新种类，其在刚性呋喃糖糖环上同时带有氨基和羧基。四个这样的分子，6-氨基-2,5-脱水-6-脱氧-D-葡萄糖酸（3，Gaa）及其甘露糖醛酸（4，Maa），偶氮（5，Iaa）和3,4-二氧杂豆酸合成了（6，ddIaa）同源物。合成遵循新的反应路径，其中在γ-吡啶鎓重铬酸吡啶鎓羟基氧化过程中，发生了γ-苄氧基氧与己糖衍生的末端氮丙啶环在2中的分子内5-exo S（N）2开环基团具有羧基功能，导致一步形成呋喃糖糖氨基酸骨架。将这些呋喃类糖氨基酸掺入亮氨酸脑啡肽中代替其Gly-Gly部分，得到类似物8-11。通过圆二色性（CD）和各种NMR技术，结合受限的分子动力学（MD）模拟，对这些分子进行了详细的结构分析，结果表明，这些类似物中的两个8a和10a具有折叠结构，由不寻常的九元伪β-在LeuN
• [EN] HYDROGENATION OF A COMPOSITION COMPRISING HYDROXYMETHYLFURFURAL, BISHYDROXYMETHYLFURAN OR MIXTURES THEREOF<br/>[FR] HYDROGÉNATION D'UNE COMPOSITION COMPRENANT DE L'HYDROXYMÉTHYLFURFURAL, DU BISHYDROXYMÉTHYLFURANE OU DES MÉLANGES DE CEUX-CI
  申请人：BASF SE

  公开号：WO2018087270A1

  公开（公告）日：2018-05-17

  The invention relates to a process for the hydrogenation of a composition comprising hydroxymethylfurfural, bishydroxymethylfuran or mixtures thereof to obtain a composition comprising cis-(tetrahydrofuran-2,5-diyl)dimethanol and trans-(tetrahydrofuran-2,5-diyl)dimethanol. The invention also relates to a composition comprising cis-(tetrahydrofuran-2,5-diyl)dimethanol and trans-(tetrahydrofuran-2,5-diyl)dimethanol. Further, the invention also relates to a use of transition metal complex as hydrogenation catalyst for composition comprising hydroxymethylfurfural, bishydroxymethylfuran or mixtures thereof. The invention also relates to a use of the composition comprising cis-(tetrahydrofuran-2,5-diyl)dimethanol and trans-(tetrahydrofuran-2,5-diyl)dimethanol for polymerization reactions.

  该发明涉及一种用于氢化包括羟甲基糠醛、双羟甲基呋喃或二者混合物的组合物的过程，以获得包括顺式-(四氢呋喃-2,5-二基)二甲醇和反式-(四氢呋喃-2,5-二基)二甲醇的组合物。该发明还涉及一种包括顺式-(四氢呋喃-2,5-二基)二甲醇和反式-(四氢呋喃-2,5-二基)二甲醇的组合物。此外，该发明还涉及过渡金属配合物作为氢化催化剂用于包括羟甲基糠醛、双羟甲基呋喃或二者混合物的组合物。该发明还涉及使用包括顺式-(四氢呋喃-2,5-二基)二甲醇和反式-(四氢呋喃-2,5-二基)二甲醇的组合物进行聚合反应。
• [EN] HYDROGENATION OF SUBSTITUTED FURANS CATALYZED BY NHC-CONTAINING LIGANDS<br/>[FR] HYDROGÉNATION DE FURANES SUBSTITUÉS CATALYSÉS PAR DES LIGANDS CONTENANT DU NHC
  申请人：BASF SE

  公开号：WO2018220003A1

  公开（公告）日：2018-12-06

  The present invention relates to a process for the hydrogenation of a composition comprising hydroxymethylfurfural, bishydroxymethylfuran or mixtures thereof to obtain a composition comprising cis-(tetrahydrofuran-2,5-diyl)dimethanoland trans-(tetrahydrofuran-2,5-diyl)dimethanol. The invention also relates to a composition comprising cis-(tetrahydrofuran-2,5-diyl)dimethanol and trans-(tetrahydrofuran-2,5-diyl)dimethanol. Further, the invention also relates to a use of transition metal complex as hydrogenation catalyst for composition comprising hydroxymethylfurfural, bishydroxymethylfuran or mixtures thereof. The invention also relates to a use of the composition comprising cis-(tetrahydrofuran-2,5-diyl)dimethanol and trans-(tetrahydrofuran-2,5-diyl)dimethanol for polymerization reactions.

  本发明涉及一种将羟甲基糠醛、双羟甲基呋喃或其混合物加氢得到含顺式-(四氢呋喃-2,5-二基)二甲醇和反式-(四氢呋喃-2,5-二基)二甲醇的组合物的方法。本发明还涉及一种包含顺式-(四氢呋喃-2,5-二基)二甲醇和反式-(四氢呋喃-2,5-二基)二甲醇的组合物。此外，本发明还涉及过渡金属配合物作为羟甲基糠醛、双羟甲基呋喃或其混合物加氢催化剂的用途。本发明还涉及使用包含顺式-(四氢呋喃-2,5-二基)二甲醇和反式-(四氢呋喃-2,5-二基)二甲醇的组合物进行聚合反应的用途。
• Studies toward a Library of Tetrahydrofurans: Click and MCR Products of Mono- And Bis-Tetrahydrofurans
  作者：Jitendra K. Mishra、Peter Wipf、Subhash C. Sinha

  DOI：10.1021/cc1000709

  日期：2010.9.13

  Mono- and bis-tetrahydrofuran-based chemical libraries with diverse structural features have been prepared using the Sharpless azide-alkyne Click reaction and multi-component reactions (MCRs) such as Ugi and Biginelli reactions. Mono- and bis-tetrahydrofuran methyl azides, amines and ureas were key intermediates in these processes, and they were synthesized from the corresponding tetrahydrofuran methyl alcohols by mesylation followed by substitution with azide, reduction of the azide to the amine, and urea formation, as needed. Most mono- and tetrahydrofuran methyl alcohols were obtained by a Sharpless asymmetric dihydroxylation reaction. Alternatively, several mono-tetrahydrofurans were prepared by a cobalt(II) complex-catalyzed oxidative cyclization of bis-homoallylic alcohols, which were obtained by copper(I) iodide-catalyzed epoxide opening of 5,6-epoxyhex-1-ene with various alkyl and aryl Grignard reagents. These compounds are examples of an entirely new class of molecules in hitherto unknown chemical space, though their functions are yet to be determined presumably through random screening.
• URBAS, BRANKO
  作者：URBAS, BRANKO

  DOI：——

  日期：——