4-(乙酰氧基甲基)-2-呋喃酮 | 81189-55-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 中文名称: 4-(乙酰氧基甲基)-2-呋喃酮
• 中文别名: (5-羰基-2,5-二氢呋喃-3-基)甲基乙酸酯
• 英文名称: acetic acid 5-oxo-2,5-dihydrofuran-3-ylmethyl ester
• 英文别名: (5-oxo-2,5-dihydrofuran-3-yl)methyl acetate；4-(Acetoxymethyl)-2(5H)-furanone；4-acetoxymethylfuran-2(5H)-one；3-acetoxymethylbutenolide；(5-oxo-2H-furan-3-yl)methyl acetate
• CAS: 81189-55-1
• 化学式: C₇H₈O₄
• 分子量: 156.138
• InChiKey: YVHBEOMCXBXWAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(乙酰氧基甲基)-2-呋喃酮 在 蔗糖 作用下， 以60%的产率得到(S)-4-acetoxy-methyl-dihydrofuran-2-one
  参考文献：
  名称：

  Asymmetric reduction of 3-hydroxymethylbutenolide derivatives by bakers' yeast: A new approach to the synthesis of factor-I

  摘要：

  Bakers' yeast reduction of 3-benzyloxymethylbutenolide gave (S)-3-benzyloxymethylbutanolide, and its transformation to Factor-I, the autoregulator of Streptomyces viridocchromogenes, was examined.

  DOI：

  10.1016/0957-4166(92)80012-l
• 作为产物：
  描述：

  2-bromo-2-(bromomethyl)succinic acid 在 sodium tetrahydroborate 、 乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 4-(乙酰氧基甲基)-2-呋喃酮
  参考文献：
  名称：

  A facile chemoenzymatic approach to natural cytotoxic ellipsoidone A and natural ellipsoidone B

  摘要：

  Starting from citraconic anhydride (3) a facile four-step synthesis of deoxyellipsoidone 8 has been reported with 37% overall yield. An elegant six-step access to naturally occurring cytotoxic ellipsoidone A (1) and ellipsoidone B (2) has been reported with good overall yields, via the conversion of itaconic anhydride (9) to the acetoxymethylmaleic anhydride (11), regioselective sodium borohydride reduction of anhydride 11 to acetoxymethylbutyrolactone 12, Knoevenagel condensation of lactone 12 with 5-methylfurfural, selenium dioxide induced oxidation of the formed butenolide 13 and an Amano PS catalyzed deacylation of the formed diacetoxybutenolide 14 as a pathway. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.020

文献信息

• Application of the Palladium-Catalysed Norbornene-Assisted Catellani Reaction Towards the Total Synthesis of (+)-Linoxepin and Isolinoxepin
  作者：Zafar Qureshi、Harald Weinstabl、Marcel Suhartono、Hongqiang Liu、Pierre Thesmar、Mark Lautens

  DOI：10.1002/ejoc.201402218

  日期：2014.7

  the reliable and scalable synthesis of architecturally complex scaffolds. This report outlines the synthetic approaches towards this interesting class of biologically active molecules. After the key Catellani/Heck reaction, our synthesis features a Leimeux-Johnson oxidation and a titanium tetrachloride mediated aldol condensation. Finally, a tuneable Mizoroki-Heck reaction was performed to furnish not

  我们不断努力开发高选择性过渡金属催化的 CH 活化过程，从而扩大了 Catellani 反应。在 Pd-0/Pd-II/Pd-IV 催化的多米诺反应中，芳基碘、烷基碘和丙烯酸叔丁酯结合合成了新型木脂素 (+)-linoxepin 的碳骨架。对映选择性合成突出了我们小组完成的工作，并为结构复杂的支架的可靠和可扩展合成提供了极好的程序。本报告概述了此类有趣的生物活性分子的合成方法。在关键的 Catellani/Heck 反应之后，我们的合成具有 Leimeux-Johnson 氧化和四氯化钛介导的羟醛缩合。最后，
• Gas-phase fragmentation of γ-lactone derivatives by electrospray ionization tandem mass spectrometry
  作者：Antonio E. M. Crotti、Erika S. Bronze-Uhle、Paulo G. B. D. Nascimento、Paulo M. Donate、Sérgio E. Galembeck、Ricardo Vessecchi、Norberto P. Lopes

  DOI：10.1002/jms.1682

  日期：——

  Fragmentation reactions of β‐hydroxymethyl‐, β‐acetoxymethyl‐ and β‐benzyloxymethyl‐butenolides and the corresponding γ‐butyrolactones were investigated by electrospray ionization tandem mass spectrometry (ESI‐MS/MS) using collision‐induced dissociation (CID). This study revealed that loss of H2O [M + H −18]+ is the main fragmentation process for β‐hydroxymethylbutenolide (1) and β‐hydroxymethyl‐γ‐butyrolactone

  使用碰撞诱导解离（CID）通过电喷雾电离串联质谱（ESI-MS / MS）研究了β-羟甲基，β-乙酰氧基甲基和β-苄氧基甲基-丁烯化物与相应的γ-丁内酯的裂解反应。这项研究表明，H 2 O [M + H -18] +的损失是β-羟甲基丁烯内酯（1）和β-羟甲基γ-丁内酯（2）的主要裂解过程。烯酮（[M + H -42] +）的丢失是质子化的β-乙酰氧基甲基-γ-丁内酯（4）的主要裂解过程，而β-乙酰氧基甲基丁烯内酯（3）的主要裂解过程。苄基阳离子（m / z91）是β-苄氧基甲基丁烯内酯（5）和β-苄氧基甲基γ-丁内酯（6）的ESI-MS / MS光谱中的主要离子。β-位不同的侧链和双键的存在提供了一些产物离子，这些离子对于每种化合物的结构鉴定都非常重要。质子化和气相裂解过程涉及的高能方面是根据通过计算量子化学获得的热化学数据进行解释的。版权所有©2009 John Wiley＆Sons，Ltd
• From Tetronic Acid and Furfural to C(4)-Halogenated, Vinylated and Formylated Furan-2(5H)-ones and Their 5-Alkoxy Derivatives
  作者：E. Lattmann、H. M. R. Hoffmann

  DOI：10.1055/s-1996-4156

  日期：1996.1

  Tetronic acid and furfural have been elaborated into the title compounds. Palladium-catalyzed cross coupling with vinylstannanes and controlled ozonolysis followed by anhydrous workup are key reactions.

  标题化合物由四氢呋喃酸和糠醛合成。关键反应包括钯催化的乙烯基锡烷交叉偶联反应、受控的臭氧分解反应和无水处理。
• Patient interface
  申请人：KONINKLIJKE PHILIPS N.V.

  公开号：US10751495B2

  公开（公告）日：2020-08-25

  The present invention relates to patient interfaces optically indicating a user that a member of the patient interface needs to be replaced due to wear. In particular, the present invention relates to a member for patient interface which includes at least one functional material having a predefined functionality and at least one indicator wherein the concentration of the at least one indicator in the member correlates with the predefined functionality of the at least one functional material.

  本发明涉及病人界面，通过光学方式向用户指示病人界面的部件因磨损而需要更换。特别是，本发明涉及一种病人界面部件，它包括至少一种具有预定功能的功能材料和至少一种指示器，其中部件中至少一种指示器的浓度与至少一种功能材料的预定功能相关。
• Parallel Synthesis:  A New Approach for Developing Analytical Internal Standards. Application to the Analysis of Patulin by Gas Chromatography−Mass Spectrometry
  作者：Montserrat Llovera、Mercè Balcells、Mercè Torres、Ramon Canela

  DOI：10.1021/jf0513157

  日期：2005.8.1

  The polymer-assisted reaction of 4-(hydroxymethyl)furan-2(5H)-one (4HM2F) with 21 carboxylic acids using polystyrene-carbodiimide (PS-carbodiimide) yielded an ester library. Four of the esters, (5-oxo-2,5-dihydrofuran-3-yl)methyl acetate (IS-1), (5-oxo-2,5-dihydrofuran-3-yl)methyl butyrate (IS-2), (5-oxo-2,5-dihydrofuran-3-yl)methyl 2-methylpropanoate (IS-3), and (5-oxo-2,5-dihydrofuran-3-yl)methyl chloroacetate (IS-4), were tested as internal standards for the quantification of patulin in apple juice by gas chromatography-mass spectrometry in the selected ion monitoring mode (GC-MS-SIM). The developed method combines an AOAC official extractive step and a GC-MS-SIM analysis. Using a chromatographic column containing trifluoropropylmethylpolysiloxane as the stationary phase and IS-1 as the internal standard, it was possible to perform an accurate and precise quantification of underivatizated patulin in apple juice at concentrations down to 6 mu g/L. A detection limit of 1 mu g/L was established.