methyl (1S,2S,4R,7R,9S,10S,11R,13S)-9-methoxy-15-methyl-14-oxo-4-phenyl-3,5,8-trioxatetracyclo[8.6.0.01,13.02,7]hexadec-15-ene-11-carboxylate | 910324-25-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: methyl (1S,2S,4R,7R,9S,10S,11R,13S)-9-methoxy-15-methyl-14-oxo-4-phenyl-3,5,8-trioxatetracyclo[8.6.0.01,13.02,7]hexadec-15-ene-11-carboxylate
• CAS: 910324-25-3
• 化学式: C₂₃H₂₆O₇
• 分子量: 414.455
• InChiKey: MKJRQBQDWHVCFJ-SYODLGTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (1S,2S,4R,7R,9S,10S,11R,13S)-9-methoxy-15-methyl-14-oxo-4-phenyl-3,5,8-trioxatetracyclo[8.6.0.01,13.02,7]hexadec-15-ene-11-carboxylate 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 silver fluoride 、 barium carbonate 、 potassium iodide 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 methyl (1S,4S,4aS,5R,6aS,9aS)-1-benzoyloxy-4-methoxy-8-methyl-2-methylidene-7-oxo-1,4,4a,5,6,6a-hexahydropentaleno[1,6a-c]pyran-5-carboxylate
  参考文献：
  名称：

  Enantiospecific Approach toward Pentalenolactone

  摘要：

  The enantiospecific assembly of the pentalenolactones' carbon skeleton was achieved in 17 steps and 16% overall yield from methyl alpha-D-glucopyranoside. The synthetic strategy relies on two highly efficient key steps: an exo-diastereoselective Diels-Alder reaction and a nonsymmetric ozonolysis.

  DOI：

  10.1021/ol061390i
• 作为产物：
  描述：

  (1S,2S,3S,5R,8R,10S,11S,12R)-10-methoxy-5-phenyl-4,6,9-trioxatetracyclo[10.2.1.0^2,11.0^3,8]pentadec-13-ene-2-carbaldehyde 在 氢氧化钾 、 碳酸氢钠 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 20.58h， 生成 methyl (1S,2S,4R,7R,9S,10S,11R,13S)-9-methoxy-15-methyl-14-oxo-4-phenyl-3,5,8-trioxatetracyclo[8.6.0.01,13.02,7]hexadec-15-ene-11-carboxylate
  参考文献：
  名称：

  Enantiospecific Approach toward Pentalenolactone

  摘要：

  The enantiospecific assembly of the pentalenolactones' carbon skeleton was achieved in 17 steps and 16% overall yield from methyl alpha-D-glucopyranoside. The synthetic strategy relies on two highly efficient key steps: an exo-diastereoselective Diels-Alder reaction and a nonsymmetric ozonolysis.

  DOI：

  10.1021/ol061390i

文献信息

• Enantiospecific Approach toward Pentalenolactone
  作者：Sebastián A. Testero、Rolando A. Spanevello

  DOI：10.1021/ol061390i

  日期：2006.8.1

  The enantiospecific assembly of the pentalenolactones' carbon skeleton was achieved in 17 steps and 16% overall yield from methyl alpha-D-glucopyranoside. The synthetic strategy relies on two highly efficient key steps: an exo-diastereoselective Diels-Alder reaction and a nonsymmetric ozonolysis.