[(2R,3R,4R,5R)-3,4-diacetyloxy-5-[2,4-dioxo-3,3-bis(prop-2-enyl)pyridin-1-yl]oxolan-2-yl]methyl acetate | 1115195-62-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(2R,3R,4R,5R)-3,4-diacetyloxy-5-[2,4-dioxo-3,3-bis(prop-2-enyl)pyridin-1-yl]oxolan-2-yl]methyl acetate
• CAS: 1115195-62-4
• 化学式: C₂₂H₂₇NO₉
• 分子量: 449.458
• InChiKey: RAVONHHXTZXWIX-VBSBHUPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,5R)-3,4-diacetyloxy-5-[2,4-dioxo-3,3-bis(prop-2-enyl)pyridin-1-yl]oxolan-2-yl]methyl acetate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以80%的产率得到
  参考文献：
  名称：

  Synthesis of spiro-pyridones and spiro-quinolones by sequential palladium on carbon-catalyzed allylation and ring closing metathesis reactions

  摘要：

  A rapid and efficient strategy for the preparation of spiro-pyridones and spiro-quinolones using sequential Pd(0)/C-catalyzed allylation and ring closing metathesis reactions is described. The developed protocol features a fully regioselective allylation at C3 taking advantage of the unusual reactivity of Pd(0)/C catalyst. Application of the present methodology in nucleoside chemistry has also been investigated. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.11.026
• 作为产物：
  描述：

  乙酸烯丙酯 、 1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-4-hydroxy-2-pyridinone 在 1% Pd/C 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以85%的产率得到[(2R,3R,4R,5R)-3,4-diacetyloxy-5-[2,4-dioxo-3,3-bis(prop-2-enyl)pyridin-1-yl]oxolan-2-yl]methyl acetate
  参考文献：
  名称：

  Synthesis of spiro-pyridones and spiro-quinolones by sequential palladium on carbon-catalyzed allylation and ring closing metathesis reactions

  摘要：

  A rapid and efficient strategy for the preparation of spiro-pyridones and spiro-quinolones using sequential Pd(0)/C-catalyzed allylation and ring closing metathesis reactions is described. The developed protocol features a fully regioselective allylation at C3 taking advantage of the unusual reactivity of Pd(0)/C catalyst. Application of the present methodology in nucleoside chemistry has also been investigated. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.11.026