[(E,2R)-2-acetyloxy-5-oxopent-3-enyl] acetate | 58886-31-0

• 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: [(E,2R)-2-acetyloxy-5-oxopent-3-enyl] acetate
• CAS: 58886-31-0
• 化学式: C₉H₁₂O₅
• 分子量: 200.191
• InChiKey: RYPBXYWWHLDNPK-CDAZIORVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-羟基香豆素 、 [(E,2R)-2-acetyloxy-5-oxopent-3-enyl] acetate 在 L-脯氨酸 作用下， 以 乙酸乙酯 为溶剂， 反应 17.0h， 以45%的产率得到(1'S)-2-(1',2'-di-O-acetyl-D-glyceritol-1'-yl)-2H,5H-pyrano[3,2-c]benzopyran-5-one
  参考文献：
  名称：

  Diastereoselective annulation of 4-hydroxypyran-2H-ones with enantiopure 2,3-dideoxy-α,β-unsaturated sugar aldehydes derived from respective glycals

  摘要：

  One-pot condensations of 4-hydroxypyran-2H-ones 1 and 2, respectively, with various enantiopure 2,3-dideoxy-alpha,beta-unsaturated carbohydrate enals in the presence of L-proline in EtOAc at room temperature generated pyrano-pyrones. It was observed that, while benzyl-protected carbohydrate enals on condensation with 1 or 2 under the above conditions produced ail inseparable diastereomeric mixture in a ratio of 1:1, the acyl-protected carbohydrate enals on treatment with 1 or 2 under identical conditions yielded products with moderate to very high diastereoselectivity. A remarkable asymmetric induction was noticed from the C-4 stereogenic center of the acyl-protected carbohydrate enals. An almost complete diastereoselectivity was observed in those reactions that involved condensation of 1 with acetyl-protected enals 5 and 7. The reaction of 2 with 5 also proceeded diastereoselectively to furnish the corresponding annulated product. The reaction presumably took place by C-1,2-addition of the pyrone onto the iminium salt of the alpha,beta-unsaturated carbohydrate enal generated in situ, followed by beta-elimination and cyclization of the 1-oxatriene involving a 6 pi-electron electrocyclic process to yield a 2H,5H-pyrano[3,2-c]pyran-5-one derivative. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.02.018
• 作为产物：
  描述：

  乙酸酐 、 3,4-di-O-acetyl-D-arabinal 生成 [(E,2R)-2-acetyloxy-5-oxopent-3-enyl] acetate
  参考文献：
  名称：

  The formation of α,β-unsaturated aldehydes in the hydrolysis of acetylated glycals

  摘要：

  DOI：

  10.1016/s0008-6215(00)85863-2