3-acetyl-5-C-(2,3-O-isopropylidene-1,4-anhydro-β-D-erythrofuranosyl)-2-methylfuran | 97443-02-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 3-acetyl-5-C-(2,3-O-isopropylidene-1,4-anhydro-β-D-erythrofuranosyl)-2-methylfuran
• 英文别名: 1-[5-(2',3'-O-isopropylidene-β-D-erythrofuranosyl)-2-methylfuran-3-yl]ethanone；1-[5-((3aR)-2,2-dimethyl-(3ar,6ac)-tetrahydro-furo[3,4-d][1,3]dioxol-4c-yl)-2-methyl-[3]furyl]-ethanone；1-[5-((3aR)-2,2-Dimethyl-(3ar,6ac)-tetrahydro-furo[3,4-d][1,3]dioxol-4c-yl)-2-methyl-[3]furyl]-aethanon
• CAS: 97443-02-2；97550-01-1
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: PKGPXWVHDSQWJX-FRRDWIJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  57.9
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-acetyl-5-C-(2,3-O-isopropylidene-1,4-anhydro-β-D-erythrofuranosyl)-2-methylfuran 、 间硝基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以79%的产率得到(E)-1-[5-C-(2,3-O-isopropylidene-1,4-anhydro-β-D-erythrofuranosyl)-2-methylfuran]-3-(3-nitrophenyl)prop-2-en-1-one
  参考文献：
  名称：

  C-Furyl glycosides, I: Synthesis and antimicrobial evaluation of C-furyl glycosides and chalcones derived therefrom

  摘要：

  New C-furyl glycosides were synthesized in order to increase the number of compounds screened for antimicrobial activity. The antimicrobial activity showed that the bromo as well as the nitro derivatives were the most active compounds.

  DOI：

  10.1007/s00706-008-0941-1
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 copper(II) sulfate 、 丙酮 作用下， 生成 3-acetyl-5-C-(2,3-O-isopropylidene-1,4-anhydro-β-D-erythrofuranosyl)-2-methylfuran
  参考文献：
  名称：

  30.葡萄糖和β-二酮的缩合

  摘要：

  DOI：

  10.1039/jr9450000116

文献信息

• 5-(5-Aryl-1,3,4-oxadiazole-2-carbonyl)furan-3-carboxylate and New Cyclic C-Glycoside Analogues from Carbohydrate Precursors with MAO-B, Antimicrobial and Antifungal Activities
  作者：Mohamed Mohamed El-Sadek、Seham Yassen Hassan、Nagwa Said Abd El-Dayem、Galila Ahmed Yacout

  DOI：10.3390/molecules17067010

  日期：——

  Cyclization of acyclic C-glycoside derivatives 1a,b to 2a,b as the major isomers, and 4a,b as the minor isomers were carried out. The isopropylidene derivatives 3a,b were prepared, as well as the hydrazide derivative 6, which was condensed with a variety of aldehydes to give hydrazones 7a–e which were also prepared from the compounds 12a–e. Acetylation of 7a,d gave the corresponding acetyl derivatives 8a,d, respectively. In addition, the dicarbonyl compound 9 was prepared in the hydrate form, which reacted with a number of aroylhydrazines to give the corresponding bisaroyl-hydrazones 10a–d, which were cyclized into 1,3,4-oxadiazoles 11a–d. Furthermore, two of the prepared compounds were examined to show the ability to activate MAO-B. In addition a number of prepared compounds showed antibacterial and antiviral activities.

  将无环 C-糖苷衍生物 1a,b 环化成主要异构体 2a,b 和次要异构体 4a,b。制备出了异亚丙基衍生物 3a、b 以及酰肼衍生物 6，后者与多种醛缩合生成了酰肼 7a-e，这些酰肼也是由化合物 12a-e 制备而成的。对 7a,d 进行乙酰化处理后，可分别得到相应的乙酰基衍生物 8a,d。此外，还制备了水合物形式的二羰基化合物 9，该化合物与一些酰肼反应生成相应的双酰肼 10a-d，然后环化成 1,3,4-噁二唑 11a-d。此外，研究还发现其中两种化合物具有激活 MAO-B 的能力。此外，一些制备的化合物还显示出抗菌和抗病毒活性。