5-((E)-2-((2S,3S,5R,6R)-3-(hydroxymethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl)vinyl)-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one | 1035190-60-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 5-((E)-2-((2S,3S,5R,6R)-3-(hydroxymethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl)vinyl)-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one
• 英文别名: 5-[(E)-2-[(2S,3S,5R,6R)-3-(hydroxymethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl]ethenyl]-2,2-dimethyl-1,3-benzodioxin-4-one
• CAS: 1035190-60-3
• 化学式: C₂₁H₂₈O₈
• 分子量: 408.449
• InChiKey: YPLOBQSUODPBOJ-MAOIMZRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-((E)-2-((2S,3S,5R,6R)-3-(hydroxymethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl)vinyl)-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (2R,3S,5R,6R)-3-((E)-2-(2,2-dimethyl-4-oxo-4H-benzo[d][1,3]dioxin-5-yl)vinyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2-carbaldehyde
  参考文献：
  名称：

  A new synthesis of (−)-epipyriculol: a phytotoxic metabolite

  摘要：

  A convenient synthesis of the phytotoxic natural product epipyriculol has been accomplished in 17 steps from methyl L-tartrate. The synthetic strategy is based upon the use of a butanediacetal-protected scaffold as central core from which the alkenyl side chains were assembled. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.115
• 作为产物：
  描述：

  5-((E)-2-((2S,3S,5R,6R)-3-((tert-butyldimethylsilyloxy)methyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl)vinyl)-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 以13%的产率得到5-((E)-2-((2S,3S,5R,6R)-3-(hydroxymethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl)vinyl)-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one
  参考文献：
  名称：

  A new synthesis of (−)-epipyriculol: a phytotoxic metabolite

  摘要：

  A convenient synthesis of the phytotoxic natural product epipyriculol has been accomplished in 17 steps from methyl L-tartrate. The synthetic strategy is based upon the use of a butanediacetal-protected scaffold as central core from which the alkenyl side chains were assembled. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.115

文献信息

• A new synthesis of (−)-epipyriculol: a phytotoxic metabolite
  作者：Antonio Leyva、Francesca E. Blum、Steven V. Ley

  DOI：10.1016/j.tet.2008.01.115

  日期：2008.5

  A convenient synthesis of the phytotoxic natural product epipyriculol has been accomplished in 17 steps from methyl L-tartrate. The synthetic strategy is based upon the use of a butanediacetal-protected scaffold as central core from which the alkenyl side chains were assembled. (C) 2008 Elsevier Ltd. All rights reserved.