3-(hydroxy-2,2,4-(trimethyl-5-pentyl-1,3-dioxolan-4-yl)-methyl)-4-methoxy-5-methylenefuran-2(5H)-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(hydroxy-2,2,4-(trimethyl-5-pentyl-1,3-dioxolan-4-yl)-methyl)-4-methoxy-5-methylenefuran-2(5H)-one
• 英文别名: 3-[(S)-hydroxy-[(4S,5S)-2,2,4-trimethyl-5-pentyl-1,3-dioxolan-4-yl]methyl]-4-methoxy-5-methylidenefuran-2-one
• 化学式: C₁₈H₂₈O₆
• 分子量: 340.417
• InChiKey: AZQOHXDERYZUGI-XLWVJDPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(hydroxy-2,2,4-(trimethyl-5-pentyl-1,3-dioxolan-4-yl)-methyl)-4-methoxy-5-methylenefuran-2(5H)-one 在 四丁基氟化铵 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 15.17h， 生成
  参考文献：
  名称：

  Total Synthesis and Biological Activity of the Proposed Structure of Phaeosphaeride A

  摘要：

  The total synthesis of the structure assigned to the natural product phaeosphaeride A la was accomplished. The key steps involve the addition of vinyllithium reagent 7 to the acetonide-protected aldehyde 8 to access the carbon backbone of la, the introduction of the methoxylamino group followed by intramolecular hetero-Michael cyclization, and methanol elimination to form the dihydropyran ring. In this study, both enantiomers of la were synthesized and tested for biological activity. Preliminary results showed that (6R,7R,8R)-1a and (6S,7S,8S)-1a inhibit STAT3-dependent transcriptional activity in a dose-dependent manner and exhibit antiproliferative properties in breast (MDA-MB-231) and pancreatic (PANC-1) cancer cells.

  DOI：

  10.1021/jo301662e
• 作为产物：
  描述：

  正己醛 在 氯磺酸 、 正丁基锂 、 甲基磺酰胺 、 三氧化硫吡啶 、 二异丁基氢化铝 、 氢化奎宁 1,4-(2,3-二氮杂萘)二醚 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 二甲基亚砜 、 叔丁醇 为溶剂， 反应 10.68h， 生成 3-(hydroxy-2,2,4-(trimethyl-5-pentyl-1,3-dioxolan-4-yl)-methyl)-4-methoxy-5-methylenefuran-2(5H)-one
  参考文献：
  名称：

  Total Synthesis and Biological Activity of the Proposed Structure of Phaeosphaeride A

  摘要：

  The total synthesis of the structure assigned to the natural product phaeosphaeride A la was accomplished. The key steps involve the addition of vinyllithium reagent 7 to the acetonide-protected aldehyde 8 to access the carbon backbone of la, the introduction of the methoxylamino group followed by intramolecular hetero-Michael cyclization, and methanol elimination to form the dihydropyran ring. In this study, both enantiomers of la were synthesized and tested for biological activity. Preliminary results showed that (6R,7R,8R)-1a and (6S,7S,8S)-1a inhibit STAT3-dependent transcriptional activity in a dose-dependent manner and exhibit antiproliferative properties in breast (MDA-MB-231) and pancreatic (PANC-1) cancer cells.

  DOI：

  10.1021/jo301662e

文献信息

• Total Synthesis and Biological Activity of the Proposed Structure of Phaeosphaeride A
  作者：Anthoula Chatzimpaloglou、Maria P. Yavropoulou、Karien E. Rooij、Ralf Biedermann、Uwe Mueller、Stefan Kaskel、Vasiliki Sarli

  DOI：10.1021/jo301662e

  日期：2012.11.2

  The total synthesis of the structure assigned to the natural product phaeosphaeride A la was accomplished. The key steps involve the addition of vinyllithium reagent 7 to the acetonide-protected aldehyde 8 to access the carbon backbone of la, the introduction of the methoxylamino group followed by intramolecular hetero-Michael cyclization, and methanol elimination to form the dihydropyran ring. In this study, both enantiomers of la were synthesized and tested for biological activity. Preliminary results showed that (6R,7R,8R)-1a and (6S,7S,8S)-1a inhibit STAT3-dependent transcriptional activity in a dose-dependent manner and exhibit antiproliferative properties in breast (MDA-MB-231) and pancreatic (PANC-1) cancer cells.