5-hydroxymethyl-5-hydroxy-2(5H)-furanone | 95016-85-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 5-hydroxymethyl-5-hydroxy-2(5H)-furanone
• 英文别名: 5-hydroxy-5-(hydroxymethyl)furan-2(5H)-one；5-hydroxy-5-(hydroxymethyl)furan-2-one
• CAS: 95016-85-6
• 化学式: C₅H₆O₄
• 分子量: 130.1
• InChiKey: OKHURISQISYXCX-UHFFFAOYSA-N

物化性质

• 沸点：
  435.0±45.0 °C(Predicted)
• 密度：
  1.557±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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-hydroxymethyl-5-hydroxy-2(5H)-furanone 在 sodium tetrahydroborate 作用下， 以45%的产率得到γ-hydroxymethyl-α,β-butenolide
  参考文献：
  名称：

  Syntheses of γ-Oxo Acids or γ-Oxo Esters by Photooxygenation of Furanic Compounds and Reduction Under Ultrasound: Application to the Synthesis of 5-Aminolevulinic Acid Hydrochloride

  摘要：

  5-hydroxymethyl-2-furfural (1a) 或衍生物 1b-g 经过光氧合反应可生成 4-hydroxy-Î 2-butenolides 2，这是丁烯内酯 3 或 α，β-不饱和 γ-oxo esters 5 的前体。在乙酸中用锌在超声条件下选择性还原烯醇内酯 2 或氧代酯 5，可得到δ-氧代酸 4 或δ-氧代酯 6。氨基衍生物 1d 光氧合后，选择性还原相应的内酯 2d，水解后得到 5-氨基乙酰丙酸盐酸盐 (7)（ALA）。

  DOI：

  10.1055/s-1995-3897
• 作为产物：
  描述：

  5-羟甲基糠醛 在 Sephadex resin 、 氧气 、 rose bengal 作用下， 以 乙醇 为溶剂， 生成 5-hydroxymethyl-5-hydroxy-2(5H)-furanone
  参考文献：
  名称：

  Syntheses of γ-Oxo Acids or γ-Oxo Esters by Photooxygenation of Furanic Compounds and Reduction Under Ultrasound: Application to the Synthesis of 5-Aminolevulinic Acid Hydrochloride

  摘要：

  5-hydroxymethyl-2-furfural (1a) 或衍生物 1b-g 经过光氧合反应可生成 4-hydroxy-Î 2-butenolides 2，这是丁烯内酯 3 或 α，β-不饱和 γ-oxo esters 5 的前体。在乙酸中用锌在超声条件下选择性还原烯醇内酯 2 或氧代酯 5，可得到δ-氧代酸 4 或δ-氧代酯 6。氨基衍生物 1d 光氧合后，选择性还原相应的内酯 2d，水解后得到 5-氨基乙酰丙酸盐酸盐 (7)（ALA）。

  DOI：

  10.1055/s-1995-3897

文献信息

• Efficient Photooxygenation of Furans using Oxygen with Wool-Immobilizing Rose Bengal as Green Photosensitizer
  作者：Yan Zhang、Wei Wang、Shushu Li

  DOI：10.14233/ajchem.2015.16745

  日期：——

  A new type of solid-supported photosensitizer was prepared from Rose Bengal and wool via acid dye dyeing process. The wool-Rose-bengal photosensitizer was characterized by Fourier transform infrared spectrometer (FTIR), scanning electron microscope and fastness test. This sensitizer was used as heterogeneous photocatalyst to promote furans oxidation to the corresponding butenolides in excellent yields (90 %). The sensitizer could be easily recovered from the reaction mixture by filtration and reused in the new cycle of the reaction.

  以玫瑰红和羊毛为原料，通过酸性染料染色工艺制备了一种新型固体支撑光敏剂。傅立叶变换红外光谱仪（FTIR）、扫描电子显微镜和牢度测试对羊毛-玫瑰红光敏剂进行了表征。这种敏化剂被用作异相光催化剂，可促进呋喃氧化成相应的丁烯内酯，收率极高（90%）。通过过滤，可以很容易地从反应混合物中回收敏化剂，并在新一轮反应中重复使用。
• Visible photostability of some ruthenium and platinum phthalocyanines in water and in the presence of organic substrates
  作者：Manuela Carchesio、Lucia Tonucci、Nicola d'Alessandro、Antonino Morvillo、Piero Del Boccio、Mario Bressan

  DOI：10.1142/s1088424610002306

  日期：2010.6

  Water-soluble, metal-tetrasubstituted phthalocyanines ( -SO₃H , MPcS and -COOH , MPcC) of platinum and ruthenium were synthesized and their photostability to visible light irradiation was determined. For the ruthenium phthalocyanines, the characteristic visible Q band of the phthalocyanines was almost totally suppressed after five days of irradiation. The platinum derivatives were instead more resistant to photodegradation, and the Q band did not decrease by more than 25%. The addition of carbonyl compounds to the phthalocyanine solution in water (at concentrations at least 1400-fold those of the phthalocyanines) dramatically accelerated the photobleaching of these phthalocyanine complexes. PtPcS turned from blue to green and to colorless with one day of visible-light irradiation in the presence of acetone. This effect decreased with the increase in molecular weight of the ketones (from acetone to 2-pentanone). The addition of alcohols (i.e. 1-butanol) or other organics (i.e. phenylacetic acid) did not affect the photostability of these metal-tetrasubstituted phthalocyanines. Dioxygen also had an important role, as when the solutions of phthalocyanines were carefully deaerated before irradiation, the visible spectra were preserved. The platinum phthalocyanines, as with the palladium analogs, sensitize the photoproduction of ¹O₂ , as shown by the formation of endoperoxide and its rearranged products in the presence of furfuryl alcohol (a singlet oxygen trapping agent).

  合成了铂和钌的水溶性金属四取代酞菁（-SO3H , MPcS 和 -COOH , MPcC），并测定了它们在可见光照射下的光稳定性。对于钌酞菁，酞菁特有的可见光 Q 波段在照射五天后几乎完全被抑制。而铂衍生物对光降解的抵抗力更强，Q 带的下降幅度不超过 25%。在酞菁水溶液中加入羰基化合物（浓度至少是酞菁的 1400 倍）会显著加速这些酞菁复合物的光漂白。在有丙酮存在的情况下，PtPcS 在可见光照射一天后就会由蓝变绿，最后变成无色。这种效果随着酮类（从丙酮到 2-戊酮）分子量的增加而减弱。加入醇类（如 1-丁醇）或其他有机物（如苯乙酸）不会影响这些金属-四代酞菁的光稳定性。二氧也起着重要作用，因为当酞菁溶液在辐照前经过仔细的脱氧处理后，其可见光谱得以保留。铂酞菁和钯酞菁类似物一样，能敏化 1O2 的光生成，在糠醇（一种单线态氧捕获剂）存在下形成的内过氧化物及其重排产物就证明了这一点。
• Water-soluble ruthenium complex-pyrene dyads with extended triplet lifetimes for efficient energy transfer applications
  作者：Arne C. Sell、Julius C. Wetzel、Matthias Schmitz、A. Wouter Maijenburg、Georg Woltersdorf、Robert Naumann、Christoph Kerzig

  DOI：10.1039/d2dt01157c

  日期：——

  with a covalently attached pyrene chromophore. The triplet energy of the latter is slightly below that of the metal complex enabling a so-called triplet reservoir and excited-state lifetime extensions of up to two orders of magnitude. The diimine co-ligands, which can be modified easily, have a major impact on both the ultrafast intramolecular energy transfer (iEnT) kinetics upon excitation with visible

  鉴于水介质中溶解氧和合适受体的浓度通常远低于有机溶剂中的浓度，激发光敏剂的长三重态寿命对于水中的有效能量转移反应至关重要。在此，我们报告了两种结构相关的水溶性钌络合物基双联体的设计、合成和光化学表征，该双联体装饰有共价连接的芘发色团。后者的三重态能量略低于金属配合物的能量，从而实现了所谓的三重态储层和高达两个数量级的激发态寿命延长。易于修饰的二亚胺共配体，对可见光激发后的超快分子内能量转移 (iEnT) 动力学和由此产生的长寿命芘三重态的寿命产生重大影响。含有菲咯啉的二元组在纯水中显示出快速的三重态芘形成 (25 ps) 和超过 50 微秒的超长三重态寿命。iEnt 过程当使用联吡啶共配体时，通过Dexter 机制的速度要慢两倍，这可以通过较差的轨道重叠来合理化。对于在空气饱和水中形成单线态氧以及在上转换机制中作为关键中间体的蒽三联体的双分子生成，这两种二元体都是非常有效的敏化剂。5-羟甲
• Covalent triazine-based frameworks – switching selectivity in HMF photooxidation
  作者：Daniel Ditz、Nina M. Sackers、Felix Müller、Mirijam Zobel、Sebastian Bergwinkl、Patrick Nuernberger、Leonie Sophie Häser、Sarah Brettschneider、Florian M. Wisser、Christoph Bannwarth、Regina Palkovits

  DOI：10.1039/d3gc01210g

  日期：——

  block depending on the activation mechanism of molecular oxygen: either oxygen is reduced and HMF is directly oxidized to 2,5-diformylfuran (DFF) or molecular oxygen is photoactivated to singlet oxygen which reacts in a cycloaddition with HMF to yield 5-hydroxy-5-hydroxymethyl-furan-2-one (H2MF). Extensive characterization of the optoelectronic properties combined with quantum chemical calculations and

  通过定制 CTF 光催化剂，可以改变 HMF 的光氧化途径。
• Perfluoralkyl/Rose Bengal Functionalized Janus Silica Nanoparticles for Photocatalytic Transformations with Singlet Oxygen
  作者：Omid Pourshiani、Zeno Romero、Nasim Ganji、Tim Herrendorf、Andreas Seifert、Anna Demchenko、Marc H. Prosenc、Wolfgang Kleist、Michael Kopnarski、Babak Karimi、Werner R. Thiel

  DOI：10.1002/cctc.202301162

  日期：2024.2.22

  Anisotropic Janus nanosheets containing electrostatically grafted Rose Bengal and highly hydrophobic fluorinated octyl groups on opposite sides were fabricated from crushed Janus hollow spheres. The material showed excellent activity in various photochemical transformations under green LED irradiation.

  各向异性的 Janus 纳米片由粉碎的 Janus 空心球制成，其两侧含有静电接枝的玫瑰红和高度疏水的氟化辛基。该材料在绿色LED照射下在各种光化学转化中表现出优异的活性。