5-bis(hydroxymethyl)tetrahydro-2-furanone | 3621-60-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 5-bis(hydroxymethyl)tetrahydro-2-furanone
• 英文别名: 5,5-bis(hydroxymethyl)dihydrofuran-2(3H)-one；5,5-bis-hydroxymethyl-dihydro-furan-2-one；5,5-Bis(hydroxymethyl)oxolan-2-one
• CAS: 3621-60-1
• 化学式: C₆H₁₀O₄
• 分子量: 146.143
• InChiKey: FKUVWTLXXIBCOJ-UHFFFAOYSA-N

物化性质

• 沸点：
  175 °C(Press: 0.2 Torr)
• 密度：
  1.302 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-bis(hydroxymethyl)tetrahydro-2-furanone 在 calcium chloride 吡啶 、 Triton X 、 Pseudomonas cepacia lipase 、 3 A molecular sieve 作用下， 以 水 、 乙腈 为溶剂， 反应 4.5h， 生成 (S)-5-[(acetyloxy)methyl]-5-(hydroxymethyl)tetrahydro-2-furanone
  参考文献：
  名称：

  酶促脱对称的5-双（羟甲基）四氢-2-呋喃酮：蛋白激酶C配体的模板

  摘要：

  在有机介质中存在假单胞菌脂肪酶的情况下，乙酸乙烯酯或肉豆蔻酸乙烯酯对内消旋-5-双（羟甲基）四氢-2-富南酮1进行立体选择性酰化，得到相应的（S）-单酯，其对映体过量很高。在相同酶的存在下，相应的二乙酸酯的水解提供了（R）-单乙酸酯。

  DOI：

  10.1016/j.tetasy.2004.01.030
• 作为产物：
  描述：

  5-bis<<(tert-butyldiphenylsilyl)oxy>methyl>tetrahydro-2-furanone 在 氟化铵 作用下， 以 甲醇 为溶剂， 反应 96.0h， 以40%的产率得到5-bis(hydroxymethyl)tetrahydro-2-furanone
  参考文献：
  名称：

  Conformationally Constrained Analogues of Diacylglycerol. 10. Ultrapotent Protein Kinase C Ligands Based on a Racemic 5-Disubstituted Tetrahydro-2-furanone Template

  摘要：

  5,5-Bis(hydroxymethyl)tetrahydro-2-furanone and its isomer 4,4-bis(hydroxymethyl)tetrahydro-2-furanone were investigated as possible templates for the construction of conformationally constrained analogues of the biologically important second messenger, diacylglycerol (DAG). The former lactone contains embedded within its structure an exact glycerol moiety, while in the latter the ring oxygen has been transposed to the other side of the carbonyl group. Al target compounds were synthesized as racemates from 1,3-dihydroxy-2-propanone. The 5,5-bis(hydroxymethyl)tetrahydro-2-furanone proved to be the better template for the construction of DAG surrogates that were demonstrated to have high binding affinities for the biological target, protein kinase C (PK-C). The simplest target compounds derived from this template (3e and 3f) have one of the hydroxyl moieties functionalized either as a myristate or as an oleate ester. The simplest target compound (9e) derived from the ineffective 4,4-bis(hydroxymethyl)tetrahydro-2-furanone template was investigated only with a myristoyl acyl chain. Reducing the long acyl chain to an acetyl moiety and attaching a compensating lipophilic chain to the lactone ring as an alpha-alkylidene moiety produced compounds 10e and 10f(Z-isomers) and 11e and 11f(E-isomers), which were constructed on the more effective 5,5-bis(hydroxymethyl)tetrahydro-2-furanone template. Targets 14c (Z-isomer) and 15c (E-isomer) were derived, in turn, from 4,4-bis(hydroxymethyl)tetrahydro-2-furan. The affinities of these ligands for PK-C were assessed in terms of their ability to displace bound [H-3-20]phorbol 12,13-dibutyrate (PDBU) from the single isozyme PK-C alpha. The biological data support the hypothesis that the increase in binding affinity for PK-C shown by some of these constrained DAG mimetics appears to be entropic in nature. Two of the designed ligands (10e and 10f) showed the highest affinities (34 and 24 nM, respectively) reported so far for a DAG analogue. Assuming that the interaction between these racemic compounds and PK-C is stereospecific, the potency of the active enantiomer is anticipated to double.

  DOI：

  10.1021/jm950276v

文献信息

• Site-Selective and Stereoselective C–H Alkylations of Carbohydrates via Combined Diarylborinic Acid and Photoredox Catalysis
  作者：Victoria Dimakos、Hsin Y. Su、Graham E. Garrett、Mark S. Taylor

  DOI：10.1021/jacs.9b01531

  日期：2019.4.3

  Diphenylborinic acid serves as a cocatalyst for site- and stereoselective C-H alkylation reactions of carbohydrates under photoredox conditions using quinuclidine as the hydrogen atom transfer mediator. Products arising from selective abstraction of the equatorial hydrogens of cis-1,2-diol moieties, followed by C-C bond formation with net retention of configuration, are obtained. Computational modeling supports

  二苯基硼酸在光氧化还原条件下用作碳水化合物的位点和立体选择性 CH 烷基化反应的助催化剂，使用奎宁环作为氢原子转移介体。获得了选择性提取顺式 1,2-二醇部分的赤道氢，然后形成 CC 键并保留构型的产物。计算模型支持涉及形成四配位硼酸酯的机制，该机制通过极性匹配和/或离子配对效应加速氢原子与奎宁环衍生的自由基阳离子的转移。
• Conformationally constrained diacylglycerol analogues
  申请人：The United States of America as represented by the Department of Health

  公开号：US05874464A1

  公开（公告）日：1999-02-23

  Conformationally constrained diacylglycerol analogues, pharmaceutical compositions comprising such analogues, and methods of using such analogues as agonists and antagonists of protein kinase C.

  构象受限的二酰基甘油类似物，包含这种类似物的药物组合物，以及使用这种类似物作为蛋白激酶C的激动剂和拮抗剂的方法。
• Photocatalyzed Carbon−Carbon Bond Formation Between Glycerol and Electron‐Deficient Olefins
  作者：Kassem El‐Chami、Robert Madsen

  DOI：10.1002/cctc.202301143

  日期：2023.12.19

  Valorization of glycerol can be achieved by photocatalytic coupling at C2 with electron-deficient olefins. With [Ir(dF(CF3)ppy)2(dtbpy)]PF6 as the photocatalyst (PC) coupling to acrylates can be performed while (Bu4N)4W10O32 as the photocatalyst allows for further coupling to fumaronitrile, N-methyl maleimide and itaconic anhydride.

  甘油的增值可以通过在C2处与缺电子烯烃的光催化偶联来实现。使用[Ir(dF(CF 3 )ppy) 2 (dtbpy)]PF 6作为光催化剂(PC)可以与丙烯酸酯偶联，而(Bu 4 N) 4 W 10 O 32作为光催化剂则可以进一步与富马腈偶联，N-甲基马来酰亚胺和衣康酸酐。
• Photoredox‐Catalyzed α−C−H Monoalkylation of Symmetric Polyols in the Presence of CO₂
  作者：Gaétan Archer、Ricardo Meyrelles、Isabel Eder、Nóra Kovács、Boris Maryasin、Maurice Médebielle、Jérémy Merad

  DOI：10.1002/anie.202315329

  日期：2024.2.5

  The transient carbonation of polyols under a CO2 atmosphere enables their C−H monoalkylation by photoredox catalysis. This reactivity results from an unprecedented C−H activation through intramolecular hydrogen bonding.

  多元醇在CO 2气氛下的瞬时碳酸化使其能够通过光氧化还原催化进行CH单烷基化。这种反应性是通过分子内氢键前所未有的 C−H 活化产生的。
• DIACYLGLYCEROL LACTONE COMPOUND, PREPARATION METHOD THEREFOR, AND IMMUNOSTIMULATOR CONTAINING SAME AS ACTIVE INGREDIENT
  申请人：Enzychem Lifesciences Corporation

  公开号：EP3750882A1

  公开（公告）日：2020-12-16

  Disclosed are a novel diacylglycerol lactone compound that promotes neutrophil migration to enhance immunity and inhibit infection, a method for preparing the same, and an immunostimulator containing the same as an active ingredient. The diacylglycerol lactone compound is represented by Chemical formula 1 in the specification. In Chemical formula 1, R1 and R2 are independently a fatty acid residue of 2 to 30 carbon atoms.

  本发明公开了一种促进中性粒细胞迁移以增强免疫力和抑制感染的新型二酰甘油内酯化合物、制备该化合物的方法以及含有该化合物作为活性成分的免疫刺激剂。二酰甘油内酯化合物在说明书中用化学式 1 表示。在化学式 1 中，R1 和 R2 独立地为 2 至 30 个碳原子的脂肪酸残基。