2-deoxy-2-fluoro-D-arabinono-1,4-lactone | 129870-02-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 2-deoxy-2-fluoro-D-arabinono-1,4-lactone
• 英文别名: (3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-one
• CAS: 129870-02-6
• 化学式: C₅H₇FO₄
• 分子量: 150.107
• InChiKey: BJBFQBMSTLSCKO-FLRLBIABSA-N

物化性质

• 沸点：
  385.9±42.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-deoxy-2-fluoro-D-arabinono-1,4-lactone 在 phosphorus pentoxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.75h， 生成 (2R,3R,4S)-4-Fluoro-1,3-bis-methoxymethoxy-5-vinyl-hept-6-ene-2,5-diol
  参考文献：
  名称：

  醛糖内酯的羟甲基化和3-脱氧-3-氟-d-果糖的化学合成

  摘要：

  摘要发现由丁基锂和（苄氧基甲基）三正丁基锡烷原位生成的（苄氧基甲基）锂是一种有效的试剂，用于将1,4-内酯单羟甲基化形成酮糖。因此，4-羟基丁酸-1,4-内酯，2-脱氧-2-氟-3,5-二-O-（甲氧基甲基）-d-阿拉伯糖基-1,4-内酯，2,3,5-三-O-（甲氧基甲基）-d-阿拉伯基-1,4-内酯，5-O-（甲氧基甲基）-2,3-O-亚甲基-d-ribono-1,4-内酯，2,3,5,6 -四-O-（甲氧基甲基）-d-altrono-1,4-内酯，2,3：5,6-di-O-异亚丙基-d-gulono-1,4-内酯和2,3-O-异亚丙基将-1-赤藓基-1,4-内酯分别转化为1-苄氧基-5-羟基-2-戊酮，1-O-苄基-3-脱氧-3-氟-4,6-二-O-（甲氧基甲基）-d-果糖呋喃糖，1-O-苄基-3,4,6-三-O-（甲氧基甲基）-d-果糖呋喃糖，1-O-苄基-6-O-（甲氧基甲基）-2

  DOI：

  10.1016/0008-6215(94)80065-0
• 作为产物：
  描述：

  ethyl (2S,3R)-3-<(2R)-1,4-dioxaspiro<4.5>decanyl>-2-fluoro-3-hydroxypropanoate 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 14.0h， 以51%的产率得到2-deoxy-2-fluoro-D-arabinono-1,4-lactone
  参考文献：
  名称：

  Synthesis of Fluorinated Macrocyclic Bis(indolyl)maleimides as Potential ¹⁹F NMR Probes for Protein Kinase C

  摘要：

  Six macrocyclic bis(indolyl)maleimides 1-6 bearing a fluorine label on the aliphatic portion of the macrocycle have been prepared as potential fluorine NMR probes for the catalytic domain of protein kinase C. The macrocyclic bis(indolyl)maleimides such as LY333531 are reversible, ATP competitive, and isoform-selective inhibitors of protein kinase C and may thus serve to probe for subtle differences between protein kinase catalytic domains. The key stereochemical elements were put in place by a Welch aldol condensation between ethyl fluoroacetate and (R)-cyclohexylidene glyceraldehyde, which was followed, by allylation of the secondary alcohol, elaboration of the alkene and ester to alcohols, and mesylation. The macrocycle was formed by slow addition of a mixture of the fluorine-labeled aliphatic dimesylate and N-methyl 2,3-bis[1H-indol-3-yl]maleimide to a suspension of cesium carbonate. Adjusting the Functionality led to the six fluorine-labeled macrocyclic bis(indolyl)maleimides. These compounds retain the high potency of the parent compounds, with IC50 values below 5 nM for the 14-membered ring compounds 1-3 and 13-90 nM for the 15-membered ring compounds 5-6. Vicinal proton-fluorine coupling constants provide an experimental parameter for determining the local macrocycle conformation.

  DOI：

  10.1021/jo9808876

文献信息

• Synthesis of 3-deoxy-3-fluoro-D-fructose
  作者：Mikael Bols、Walter A. Szarek

  DOI：10.1039/c39920000445

  日期：——

  3-Deoxy-3-fluro-D-fructose has been synthesized using a new method for making ketoses involving hydroxyalkylation of 2-deoxy-2-fluoro-D-arabinono-1,4-lactone using (benzyloxymethyl)tributylstannane–n-butyllithium.

  3-去氧-3-氟-D-果糖已经通过一种新的酮糖合成方法合成，该方法涉及使用（苄氧甲基）三正丁基锡–正丁基锂对2-去氧-2-氟-D-阿拉伯糖-1,4-内酯进行氢氧烷基化。
• Bols, Mikael; Lundt, Inge, Acta Chemica Scandinavica, 1990, vol. 44, # 3, p. 252 - 256
  作者：Bols, Mikael、Lundt, Inge

  DOI：——

  日期：——
• BOLS, MIKAEL;LUNDT, INGE, ACTA CHEM. SCAND., 44,(1990) N, C. 252-256
  作者：BOLS, MIKAEL、LUNDT, INGE

  DOI：——

  日期：——