2-deoxy-L-ascorbic acid | 182678-33-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 2-deoxy-L-ascorbic acid
• 英文别名: Desoxyascorbinsaure；(2R)-2-[(1S)-1,2-dihydroxyethyl]-3-hydroxy-2H-furan-5-one
• CAS: 182678-33-7
• 化学式: C₆H₈O₅
• 分子量: 160.127
• InChiKey: HUCQJHXRPKZZIZ-NJGYIYPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  11
• 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：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-deoxy-L-ascorbic acid 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以94%的产率得到2-bromo-2-deoxy-L-ascorbic acid
  参考文献：
  名称：

  Synthesis of 2-Deoxy-2-halo-l-ascorbic Acids

  摘要：

  2-Iodo- and 2-bromo-2-deoxy-L-ascorbic acids (2 and 3) were prepared by facile halogenation of 2-deoxy-L-ascorbic acid (6) with NIS and NBS, respectively. Likewise, chlorination with NCS produced 2-chloro-2-deoxy-L-ascorbic acid (4), but formation of 4 was accompanied by formation of the dichloro hemiketal 9. Direct fluorination of 6 with 1-chloro-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (F-TEDA-BF4) gave only the difluoro hemiketal. 10. A convenient synthesis of 2-deoxy-2-fluoro-L-ascorbic acid (5) was achieved by an indirect route. Fluorination of 2-bromo-2-deoxy-L-ascorbic acid (3) with F-TEDA-BF4 produced the bromofluoro hemiketal 16 as a mixture of diastereoisomers. Debromination with tributyltin hydride gave 5 in good yield.

  DOI：

  10.1021/jo962394b
• 作为产物：
  描述：

  (5R,6S)-4,5-Dihydroxy-6-trityloxymethyl-5,6-dihydro-pyran-2-one 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以75%的产率得到2-deoxy-L-ascorbic acid
  参考文献：
  名称：

  Synthesis of 2-Deoxy-l-ascorbic Acid

  摘要：

  DOI：

  10.1021/jo961247a

文献信息

• Micheel; Mittag, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1937, vol. 247, p. 34,40
  作者：Micheel、Mittag

  DOI：——

  日期：——
• Micheel; Hasse, Chemische Berichte, 1936, vol. 69, p. 879
  作者：Micheel、Hasse

  DOI：——

  日期：——
• [EN] HIGH BIO-RENEWABLE CONTENT INKS AND RESINS<br/>[FR] ENCRES ET RÉSINES À HAUTE TENEUR EN MATIÈRES BIO-RENOUVELABLES
  申请人：SUN CHEMICAL CORP

  公开号：WO2021231829A1

  公开（公告）日：2021-11-18

  The present invention provides novel anionic modified rosin ester resins having a high BRC content, up to 100% BRC. The resins of the present invention are useful as emulsion, dispersion, or solution resins. High BRC content pigment grind vehicles, coatings, and finished inks can be prepared using the resins of the present invention. Advantageously, the finished inks of the present invention have equal to or superior properties compared to current commercially available inks sold as sustainable products, but having little to no BRC content. The present invention represents a significant step towards developing sustainable inks and coatings that are better for the environment.