5-butyroxymethyl furfural | 81215-10-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-butyroxymethyl furfural
• 英文别名: (5-Formylfuran-2-yl)methyl butanoate
• CAS: 81215-10-3
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: ILVSPCSGYWIMMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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-butyroxymethyl furfural 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 [5-(hydroxymethyl)furan-2-yl]methyl butyrate
  参考文献：
  名称：

  五元杂芳烃与烯丙基三丁基锡烷的钯催化区域选择性烯丙基化。

  摘要：

  在这项研究中描述了钯催化的2-（氯甲基）噻吩，2-（氯甲基）呋喃和N-保护的2-（氯甲基）-1H-吡咯与烯丙基三丁基锡烷的烯丙基化反应。这种类型的烯丙基化反应区域选择性地发生在杂芳烃环上，以令人满意的产率产生烯丙基化的脱芳香化产物或烯丙基化的杂芳烃。

  DOI：

  10.1039/c4cc10373d
• 作为产物：
  描述：

  糠基丁酸酯 在 sodium carbonate 、 sodium hydrogensulfite 作用下， 以 乙醚 、 水 为溶剂， 反应 96.0h， 生成 5-butyroxymethyl 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

• 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。
• Furan-2,5-dicarboxylic acid purge process
  申请人：EASTMAN CHEMICAL COMPANY

  公开号：US10344011B1

  公开（公告）日：2019-07-09

  Disclosed is an oxidation process to produce a crude carboxylic acid product carboxylic acid product. The process comprises oxidizing a feed stream comprising at least one oxidizable compound to generate a crude carboxylic acid slurry comprising furan-2,5-dicarboxylic acid (FDCA) and compositions thereof. Also disclosed is a process to produce a dry purified carboxylic acid product by utilizing various purification methods on the crude carboxylic acid.

  本发明公开了一种氧化过程，用于生产粗羧酸产品。该过程包括将至少含有一种可氧化化合物的进料流氧化，以生成含有呋喃-2,5-二羧酸（FDCA）及其组分的粗羧酸浆。本发明还公开了一种通过利用多种纯化方法对粗羧酸进行纯化以生产干燥纯化羧酸产品的方法。
• OXIDATION PROCESS TO PRODUCE A CRUDE AND/OR PURIFIED CARBOXYLIC ACID PRODUCT
  申请人：Janka Mesfin Ejerssa

  公开号：US20120302770A1

  公开（公告）日：2012-11-29

  Disclosed is an oxidation process to produce a crude carboxylic acid product carboxylic acid product. The process comprises oxidizing a feed stream comprising at least one oxidizable compound to generate a crude carboxylic acid slurry comprising furan-2,5-dicarboxylic acid (FDCA) and compositions thereof. Also disclosed is a process to produce a dry purified carboxylic acid product by utilizing various purification methods on the crude carboxylic acid.

  本发明公开了一种氧化过程，用于生产粗羧酸产品。该过程包括将至少含有一种可氧化化合物的进料流氧化，以生成一种粗羧酸淤泥，其中包括呋喃-2,5-二羧酸（FDCA）及其组分。本发明还公开了一种利用各种纯化方法对粗羧酸进行纯化以生产干燥纯化羧酸产品的过程。
• OXIDATION PROCESS TO PRODUCE A CRUDE DRY CARBOXYLIC ACID PRODUCT
  申请人：EASTMAN CHEMICAL COMPANY

  公开号：US20140066639A1

  公开（公告）日：2014-03-06

  Disclosed is a process to produce a dry purified carboxylic acid product comprising furan-2,5-dicarboxylic acid (FDCA). The process comprises oxidizing at least one oxidizable compound selected from the following group: 5-(hydroxymethyl)furfural (5-HMF), 5-HMF esters (5-R(CO)OCH 2 -furfural where R=alkyl, cycloalkyl and aryl), 5-HMF ethers (5-R′OCH 2 -furfural, where R′=alkyl, cycloalkyl and aryl), 5-alkyl furfurals (5-R″-furfural, where R″=alkyl, cycloalkyl and aryl), mixed feed-stocks of 5-HMF and 5-HMF esters and mixed feed-stocks of 5-HMF and 5-HMF ethers and mixed feed-stocks of 5-HMF and 5-alkyl furfurals to generate a crude carboxylic acid slurry comprising FDCA, cooling a crude carboxylic acid slurry in cooling zone to form a cooled slurry stream. The cooled slurry stream is routed to a solid-liquid separation zone to generate a crude wet cake stream comprising FDCA that is dried in a drying zone to generate a dry carboxylic acid product stream comprising crude FDCA (cFDCA).

  本发明公开了一种生产干净的羧酸产品，其中包括呋喃-2,5-二羧酸（FDCA）的方法。该方法包括氧化至少一种可氧化化合物，所述可氧化化合物选自以下组：5-（羟甲基）呋喃（5-HMF），5-HMF酯（5-R（CO）OCH2-呋喃，其中R = 烷基，环烷基和芳基），5-HMF醚（5-R′OCH2-呋喃，其中R′ = 烷基，环烷基和芳基），5-烷基呋喃（5-R″-呋喃，其中R″ = 烷基，环烷基和芳基），5-HMF和5-HMF酯的混合进料以及5-HMF和5-HMF醚的混合进料和5-HMF和5-烷基呋喃的混合进料，以生成含FDCA的粗羧酸浆。在冷却区冷却粗羧酸浆以形成冷却浆流。将冷却的浆流路由到固-液分离区以生成含FDCA的粗湿蛋糕流，该流在干燥区干燥以生成干燥的羧酸产品流，其中包括粗FDCA（cFDCA）。
• FURAN-2,5-DICARBOXYLIC ACID PURGE PROCESS
  申请人：EASTMAN CHEMICAL COMPANY

  公开号：US20190337914A1

  公开（公告）日：2019-11-07

  Disclosed is an oxidation process to produce a crude carboxylic acid product carboxylic acid product. The process comprises oxidizing a feed stream comprising at least one oxidizable compound to generate a crude carboxylic acid slurry comprising furan-2,5-dicarboxylic acid (FDCA) and compositions thereof. Also disclosed is a process to produce a dry purified carboxylic acid product by utilizing various purification methods on the crude carboxylic acid.

  本发明揭示了一种氧化过程，用于生产粗羧酸产品。该过程包括氧化至少一种可氧化化合物的进料流，以产生一种含有呋喃-2,5-二羧酸（FDCA）及其组分的粗羧酸淤泥。本发明还揭示了一种通过利用各种纯化方法对粗羧酸进行纯化，以生产干燥纯化羧酸产品的方法。