5-methoxy-5-hydroxymethyl-2-furanone | 105420-94-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-methoxy-5-hydroxymethyl-2-furanone
• 英文别名: hydroxymethyl-5 methoxy-5 oxolene-3 one-2；5-(hydroxymethyl)-5-methoxyfuran-2-one
• CAS: 105420-94-8
• 化学式: C₆H₈O₄
• 分子量: 144.127
• InChiKey: NZRKONCKXWNFQX-UHFFFAOYSA-N

物化性质

• 沸点：
  340.0±42.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,5-呋喃二甲醇 在 sodium hydroxide 、 氧气 、 亚甲兰 作用下， 以 吡啶 、 甲醇 、 水 为溶剂， 反应 96.0h， 生成 5-methoxy-5-hydroxymethyl-2-furanone
  参考文献：
  名称：

  Sensitized Photooxidation of 2,5-Furanyldimethyl Dibenzoate

  摘要：

  DOI：

  10.3987/r-1986-05-1271

文献信息

• Bernasconi, Christian; Cottier, Louis; Descotes, Gerard, Bulletin de la Societe Chimique de France, 1984, vol. 2, # 7-8, p. 323 - 328
  作者：Bernasconi, Christian、Cottier, Louis、Descotes, Gerard、Nigay, Henri、Pardon, Jean-Claude、Wisniewski, Andrzej

  DOI：——

  日期：——
• Singlet-Oxygen Oxidation of 5-Hydroxymethylfurfural in Continuous Flow
  作者：Thomas S. A. Heugebaert、Christian V. Stevens、C. Oliver Kappe

  DOI：10.1002/cssc.201403182

  日期：2015.5.22

  AbstractSinglet‐oxygen oxidation of 5‐hydroxymethylfurfural (5‐HMF) was performed in continuous flow mode using rose Bengal as photosensitizer. The resulting butenolide (H2MF) was formed selectively in high yield. The procedure proved to be scalable and applicable to related bio‐based furfurals. Furthermore, preliminary data show that H2MF can be readily isomerized thermally to 5‐hydroxy‐4‐keto‐pentenoic acid oligomers.
• (2+4)-Cycloaddition with Singlet Oxygen.¹⁷O-lnvestigation of the Reactivity of Furfuryl Alcohol Endoperoxide
  作者：André M. Braun、Hans Dahn、Ernst Gassmann、Ioannis Gerothanassis、Laurent Jakob、Jordanka Kateva、Claudia G. Martinez、Esther Oliveros

  DOI：10.1111/j.1751-1097.1999.tb08295.x

  日期：1999.12

  AbstractIn earlier work, the use of furfuryl alcohol as a specific singlet oxygen acceptor was proposed because of the high ratio between the rate constants of chemical reaction and physical quenching. In contrast to furfuryl aldehyde, a number of products are formed by this type II photo‐oxidation of furfuryl alcohol. These products may be derived from the endoperoxide of furfuryl alcohol as a common intermediate. The present work focuses on the reactivity of this endoperoxide that was marked specifically by the use of 17O2 as a source for singlet oxygen. The analyses of the stable products, their yields and their labeling distribution reveal a strong solvent effect on the primary reaction pathways, and nucleophilic substitution reactions leading to hydroperoxide intermediates are dominant.
• BERNASCONI, CH.;COTTIER, L.;DESCOTES, G.;NIGAY, H.;PARDON, J. -C.;WISNIEW+, BULL. SOC. CHIM. FR., 1984, N 7-8, 323-328
  作者：BERNASCONI, CH.、COTTIER, L.、DESCOTES, G.、NIGAY, H.、PARDON, J. -C.、WISNIEW+

  DOI：——

  日期：——
• KUO YUEH-HSIUNG; SHIEH CHIR-JENG, HETEROCYCLES, 24,(1986) N 5, 1271-1274
  作者：KUO YUEH-HSIUNG、 SHIEH CHIR-JENG

  DOI：——

  日期：——