5-propionoxymethyl furfural | 76070-31-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-propionoxymethyl furfural
• 英文别名: 5-(propionyloxy)methylfurfural；2-Formyl-5-propionyloxymethyl-furan；5-propionyloxymethyl-furan-2-carbaldehyde；(5-Formylfuran-2-yl)methyl propanoate
• CAS: 76070-31-0
• 化学式: C₉H₁₀O₄
• 分子量: 182.176
• InChiKey: LRJTXVHTZSDYBN-UHFFFAOYSA-N

物化性质

• 沸点：
  81 °C(Press: 0.09 Torr)
• 密度：
  1.185 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-propionoxymethyl furfural 在 乙二胺四乙酸 、 双氧水 、 sodium carbonate 、 copper(ll) bromide 作用下， 以 水 为溶剂， 反应 3.0h， 生成 2,5-呋喃二甲酸
  参考文献：
  名称：

  一种温和条件下2,5-呋喃二甲酸的制备方法

  摘要：

  本发明公开了一种温和条件下2,5‑呋喃二甲酸的制备方法。所述制备方法包括：使包含5‑羟甲基糠醛和/或5‑羟甲基糠醛类衍生物、过氧化氢、催化剂、过氧化氢稳定剂、碱和水的混合反应体系于0～80℃反应1～24h，制得2,5‑呋喃二甲酸，所述混合反应体系的pH值为7～13。本发明提供的方法在水相中进行，使用非贵金属催化剂，过氧化氢作为氧源，通过调节pH值和添加过氧化氢稳定剂，在温和条件下高产率制备2,5‑呋喃二甲酸。本发明提供的方法绿色无污染；操作方便，工艺简单；反应物的转化率和产物2,5‑呋喃二甲酸的选择性都很高。

  公开号：

  CN112830916A
• 作为产物：
  描述：

  在 sodium carbonate 作用下， 以 乙醚 、 水 为溶剂， 以83.1%的产率得到5-propionoxymethyl furfural
  参考文献：
  名称：

  Mndzhoyan, O. L.; Avetisyan, S. A.; Nesunts, N. S., Journal of applied chemistry of the USSR, 1982, vol. 55, # 1, p. 197 - 200

  摘要：

  DOI：

文献信息

• Synthesis and Biological Evaluation of Novel Indolin-2-One Derivatives as Protein Tyrosine Phosphatase 1B Inhibitors
  作者：Hou-Ling Dai、Qiang Shen、Jian-Bin Zheng、Jing-Ya Li、Ren Wen、Jia Li

  DOI：10.2174/157017811796504909

  日期：2011.9.1

  3-Substituted indolin-2-one derivatives had been designed and synthesized as a novel class of protein tyrosine phosphatase 1B (PTP1B) inhibitors. These compounds had been evaluated for their inhibitory activities against PTP1B in vitro with IC50 values in a low micromolar range. Compound 36, the lowest, bore an IC50 value of 3.48 µ M. Preliminary structure-activity relationship was summarized.

  3-取代的吲哚啉-2-酮衍生物已被设计并合成作为一类新型的蛋白酪氨酸磷酸酶1B（PTP1B）抑制剂。这些化合物已被评估其在体外对PTP1B的抑制活性，其IC50值在低微摩尔范围内。化合物36的IC50值最低，为3.48 µM。初步的构效关系已被总结。
• CONVERSION OF CARBOHYDRATES TO HYDROXYMETHYLFURFURAL (HMF) AND DERIVATIVES
  申请人：SANBORN Alexandra J.

  公开号：US20090156841A1

  公开（公告）日：2009-06-18

  A method of producing substantially pure HMF, HMF esters and other derivatives from a carbohydrate source by contacting the carbohydrate source with a solid phase catalyst. A carbohydrate starting material is heated in a solvent in a column and continuously flowed through a solid phase catalyst in the presence of an organic acid, or heated with the organic acid and a solid catalyst in solution to form a HMF ester. Heating without organic acid forms HMF. The resulting product is purified by filtration to remove the unreacted starting materials and catalyst. The HMF ester or a mixture of HMF and HMF ester may then be oxidized to 2,5-furandicarboxylic acid (FDCA) by combining the HMF ester with an organic acid, cobalt acetate, manganese acetate and sodium bromide under pressure. Alternatively, the HMF ester may be reduced to form a furan or tetrahydrofuran diol.

  一种从碳水化合物源直接生产几乎纯的HMF、HMF酯和其他衍生物的方法是将碳水化合物源与固相催化剂接触。碳水化合物起始物质在溶剂中加热于柱中，并在有机酸存在下通过固相催化剂连续流动，或者与有机酸和溶液中的固体催化剂一起加热以形成HMF酯。在无有机酸的情况下加热会形成HMF。通过过滤将产物纯化，去除未反应的起始物质和催化剂。然后，HMF酯或HMF和HMF酯的混合物可以氧化为2,5-呋喃二甲酸（FDCA），方法是将HMF酯与有机酸、醋酸钴、醋酸锰和溴化钠在压力下结合。另外，HMF酯可以还原形成呋喃或四氢呋喃二醇。
• Effect of Extract and Synthesized Derivatives of Isolated Compound from Symplocos chinensis f. Pilosa Ohwi on Neuropathic Pain in Mice
  作者：Hyun-Yong Kim、Soo-Hyun Park、Guanglei Zuo、Kang Hyuk Kim、Seung Hwan Hwang、Hong-Won Suh、Soon-Sung Lim

  DOI：10.3390/molecules26061639

  日期：——

  Neuropathic pain is described as the “most terrible of all tortures that a nerve wound may inflict.” The aim of the present study was to demonstrate the antinociceptive effect of Symplocos chinensis f. pilosa Ohwi water extract (SCW) and synthesized derivatives of the isolated compound. The antinociceptive effect was tested using the acetic acid-induced writhing and 5% formalin tests. Antinociceptive effects on neuropathic pain were evaluated using the von Frey test with chronic constriction injury (CCI) and surgical nerve injury (SNI) models and tail-flick test with a vincristine-induced pain model. An Ames test was also conducted. 5-hydroxymethylfurfural (5-HMF) was isolated and derivatives were synthesized with various acid groups. Among the plant water extracts, SCW showed significantly effective activity. Additionally, SCW presented antinociceptive effects in the neuropathic pain models. The SCW water fraction resulted in fewer writhes than the other fractions, and isolated 5-HMF was identified as an effective compound. Because 5-HMF revealed a positive response in the Ames test, derivatives were synthesized. Among the synthesized derivations, 5-succinoxymethylfurfural (5-SMF) showed the best effect in the neuropathic pain model. Our data suggest that SCW and the synthesized compound, 5-SMF, possess effective antinociceptive activity against neuropathic pain.

  神经病性疼痛被描述为“神经伤口可能造成的所有折磨中最可怕的”。本研究的目的是证明金丝桃（Symplocos chinensis f. pilosa Ohwi）水提取物（SCW）及其孤立化合物的合成衍生物的镇痛效果。使用乙酸诱导的蠕动和5%甲醛实验来测试镇痛效果。通过使用von Frey测试评估对神经病性疼痛的镇痛效果，使用慢性缩窄损伤（CCI）和手术性神经损伤（SNI）模型以及尾部反射测试与长春碱诱导的疼痛模型。还进行了Ames试验。分离出5-羟甲基糠醛（5-HMF）并合成了带有不同酸基团的衍生物。在植物水提取物中，SCW表现出显著的有效活性。此外，SCW在神经病性疼痛模型中表现出镇痛效果。SCW水分提取物比其他分数产生更少的蠕动，分离出的5-HMF被确定为有效化合物。由于5-HMF在Ames试验中表现出积极反应，因此合成了衍生物。在合成的衍生物中，5-琥珀酰氧基甲基糠醛（5-SMF）在神经病性疼痛模型中表现出最佳效果。我们的数据表明，SCW和合成的化合物5-SMF具有有效的镇痛活性，可用于治疗神经病性疼痛。
• [EN] A PROCESS FOR PREPARING A MIXTURE COMPRISING 5-(HYDROXYMETHYL)FURFURAL AND SPECIFIC HMF ESTERS<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION D'UN MÉLANGE COMPRENANT DU 5-(HYDROXYMÉTHYL)FURFURAL ET DES ESTERS SPÉCIFIQUES DU HMF
  申请人：BASF SE

  公开号：WO2017076942A1

  公开（公告）日：2017-05-11

  The present invention relates to a process for preparing a mixture comprising 5-(hydroxy- methyl)furfural (HMF) and one or more HMF esters of formula (I, the process comprising the following steps: (A-1) preparing or providing a starting mixture comprising one, two or more carbohydrate compounds selected from the group consisting of hexoses, oligosaccharides comprising hexose units, and polysaccharides comprising hexose units, and as the solvent or as a co-solvent for said carbohydrate compounds an amount of one or more carboxylic acid esters of formula (II) (A-2) subjecting said starting mixture to reaction conditions so that at least one of said one, two or more carbohydrate compounds reacts, and a fraction of said amount of one or more carboxylic acid esters of formula (II) is hydrolyzed, so that a mixture results comprising 5-(hydroxymethyl)furfural and/or said one or more HMF esters of formula (I), one or more carboxylic acids of formula (III) and a remaining fraction of said amount of one or more carboxylic acid esters of formula (II) wherein the starting mixture prepared or provided in step (A-1) comprises a total amount of carboxylic acid esters of formula (II) of at least 50 wt.-%, based on the total weight of the starting mixture.

  本发明涉及一种制备混合物的方法，该混合物包括5-（羟甲基）糠醛（HMF）和一个或多个式（I）的HMF酯，该方法包括以下步骤：（A-1）制备或提供起始混合物，该混合物包括从己糖、包含己糖单元的寡糖和包含己糖单元的多糖组成的群体中选择的一种、两种或多种碳水化合物化合物，并将式（II）的一个或多个羧酸酯作为溶剂或共溶剂用于所述碳水化合物化合物，（A-2）将所述起始混合物置于反应条件下，以使所述一种、两种或多种碳水化合物化合物中的至少一种发生反应，并使所述式（II）的一个或多个羧酸酯的一部分水解，从而得到混合物，该混合物包括5-（羟甲基）糠醛和/或式（I）的一个或多个HMF酯、式（III）的一个或多个羧酸以及所述式（II）的一个或多个羧酸酯的剩余部分，其中在步骤（A-1）中制备或提供的起始混合物包括至少50重量％的式（II）的羧酸酯总量，基于起始混合物的总重量。
• [EN] A PROCESS FOR PREPARING FURAN-2,5-DICARBOXYLIC ACID<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION D'ACIDE FURAN-2,5-DICARBOXYLIQUE
  申请人：BASF SE

  公开号：WO2017076956A1

  公开（公告）日：2017-05-11

  The present invention relates to a process for preparing furan-2,5-dicarboxylic acid, the process comprising the following steps: (A-1) preparing or providing a starting mixture comprising one, two or more carbohydrate compounds selected from the group consisting of hexoses, oligosaccharides comprising hexose units, and polysaccharides comprising hexose units, and as the solvent or as a co-solvent for said carbohydrate compounds an amount of one or more carboxylic acid esters of formula (II) (A-2) subjecting said starting mixture to reaction conditions so that at least one of said one, two or more carbohydrate compounds reacts, and a fraction of said amount of one or more carboxylic acid esters of formula (II) is hydrolyzed, so that a mixture results comprising 5-(hydroxymethyl)furfural and/or said one or more HMF esters of formula (I), one or more carboxylic acids of formula (III) and a remaining fraction of said amount of one or more carboxylic acid esters of formula (II).

  本发明涉及一种制备呋喃-2,5-二羧酸的方法，该方法包括以下步骤：（A-1）制备或提供起始混合物，该混合物包括从由己糖组成的寡糖和多糖中选择的一种、两种或多种碳水化合物化合物，并将式（II）的一种或多种羧酸酯作为溶剂或共溶剂用于所述碳水化合物化合物中的一定量；（A-2）将所述起始混合物置于反应条件下，以使所述一种、两种或多种碳水化合物化合物中的至少一种发生反应，所述一种或多种式（I）的HMF酯和/或5-（羟甲基）呋喃，一种或多种式（III）的羧酸以及所述一种或多种羧酸酯的剩余分数混合形成。