1-[(2S,3S,4S,5R,6S)-3,4,5,6-tetramethoxyoxan-2-yl]pent-4-en-1-one | 1119827-36-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[(2S,3S,4S,5R,6S)-3,4,5,6-tetramethoxyoxan-2-yl]pent-4-en-1-one
• CAS: 1119827-36-9
• 化学式: C₁₄H₂₄O₆
• 分子量: 288.341
• InChiKey: CNMCWIZPAWOIDG-RGDJUOJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[(2S,3S,4S,5R,6S)-3,4,5,6-tetramethoxyoxan-2-yl]pent-4-en-1-one 、 甲基烯丙基溴化镁 以 四氢呋喃 为溶剂， 以99%的产率得到2-methyl-4-[[2S-(2α,3β,4α,5β,6β)]-3,4,5,6-tetramethoxytetrahydro-2H-pyran-2-yl]octa-1,7-dien-4-ol
  参考文献：
  名称：

  Conversion of Weinreb Amides into Benzene Rings Incorporating the Amide Carbonyl Carbon

  摘要：

  Esters, acids and acid chlorides can be converted via the intermediacy of their Corresponding Weinreb amides into benzene derivatives that incorporate the original carbonyl carbon as part of the benzene ring. The process involves treatment of the derived Weinreb amides with 3-butenylmagnesium bromide and an allylic Grignard reagent, followed by ring-closing metathesis, dehydration and dehydrogenation. The dehydration-dehydrogenation can be done under acidic conditions with a mixture of TsOH center dot H2O and DDQ or in two steps with SOCl2/Pyridine, followed by treatment with DDQ. Application of the method to carbohydrates provides a convenient route to C-5 aryl pyranosides.

  DOI：

  10.1021/jo802629w
• 作为产物：
  描述：

  methyl N-methoxy-N-methyl-2,3,4-tri-O-methyl-α-D-glucopyranosiduronamide 、 3-Butenylmagnesium bromide 以 四氢呋喃 为溶剂， 反应 2.0h， 以88%的产率得到1-[(2S,3S,4S,5R,6S)-3,4,5,6-tetramethoxyoxan-2-yl]pent-4-en-1-one
  参考文献：
  名称：

  Conversion of Weinreb Amides into Benzene Rings Incorporating the Amide Carbonyl Carbon

  摘要：

  Esters, acids and acid chlorides can be converted via the intermediacy of their Corresponding Weinreb amides into benzene derivatives that incorporate the original carbonyl carbon as part of the benzene ring. The process involves treatment of the derived Weinreb amides with 3-butenylmagnesium bromide and an allylic Grignard reagent, followed by ring-closing metathesis, dehydration and dehydrogenation. The dehydration-dehydrogenation can be done under acidic conditions with a mixture of TsOH center dot H2O and DDQ or in two steps with SOCl2/Pyridine, followed by treatment with DDQ. Application of the method to carbohydrates provides a convenient route to C-5 aryl pyranosides.

  DOI：

  10.1021/jo802629w

文献信息

• Conversion of Weinreb Amides into Benzene Rings Incorporating the Amide Carbonyl Carbon
  作者：Derrick L. J. Clive、Mai P. Pham

  DOI：10.1021/jo802629w

  日期：2009.2.20

  Esters, acids and acid chlorides can be converted via the intermediacy of their Corresponding Weinreb amides into benzene derivatives that incorporate the original carbonyl carbon as part of the benzene ring. The process involves treatment of the derived Weinreb amides with 3-butenylmagnesium bromide and an allylic Grignard reagent, followed by ring-closing metathesis, dehydration and dehydrogenation. The dehydration-dehydrogenation can be done under acidic conditions with a mixture of TsOH center dot H2O and DDQ or in two steps with SOCl2/Pyridine, followed by treatment with DDQ. Application of the method to carbohydrates provides a convenient route to C-5 aryl pyranosides.