methyl 2-[(E)-1-(4-hydroxyphenyl)-3-methoxy-3-oxoprop-1-en-2-yl]-1H-indole-3-carboxylate | 1431570-06-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl 2-[(E)-1-(4-hydroxyphenyl)-3-methoxy-3-oxoprop-1-en-2-yl]-1H-indole-3-carboxylate
• CAS: 1431570-06-7
• 化学式: C₂₀H₁₇NO₅
• 分子量: 351.359
• InChiKey: QXBLINQQSVKDOD-RVDMUPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  88.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-[(E)-1-(4-hydroxyphenyl)-3-methoxy-3-oxoprop-1-en-2-yl]-1H-indole-3-carboxylate 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以25%的产率得到isoprenostodione
  参考文献：
  名称：

  Synthetic approaches toward the marine alkaloid prenostodione

  摘要：

  An efficient synthesis of the core of prenostodione (3) is described herein featuring the base condensation of BOC-protected indole diesters 21 and 24 with p-methoxybenzaldehyde (22) and 4-[(t-butyldimethylsilyl)oxy]benzaldehyde (26). Attempts at selective saponification of the resultant diesters yielded isoprenostodione (3a) bearing the ester functionality at the C-3 position of the indole ring. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.02.116
• 作为产物：
  描述：

  methyl 1-benzyl-2-(2-methoxy-2-oxoethyl)-1H-indole-3-carboxylate 在 4-二甲氨基吡啶 、 aluminum (III) chloride 、 calcium hydride 、 四丁基氟化铵 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 4.5h， 生成 methyl 2-[(E)-1-(4-hydroxyphenyl)-3-methoxy-3-oxoprop-1-en-2-yl]-1H-indole-3-carboxylate
  参考文献：
  名称：

  Synthetic approaches toward the marine alkaloid prenostodione

  摘要：

  An efficient synthesis of the core of prenostodione (3) is described herein featuring the base condensation of BOC-protected indole diesters 21 and 24 with p-methoxybenzaldehyde (22) and 4-[(t-butyldimethylsilyl)oxy]benzaldehyde (26). Attempts at selective saponification of the resultant diesters yielded isoprenostodione (3a) bearing the ester functionality at the C-3 position of the indole ring. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.02.116

文献信息

• Synthetic approaches toward the marine alkaloid prenostodione
  作者：Jeanese C. Badenock、Jason A. Jordan、Gordon W. Gribble

  DOI：10.1016/j.tetlet.2013.02.116

  日期：2013.5

  An efficient synthesis of the core of prenostodione (3) is described herein featuring the base condensation of BOC-protected indole diesters 21 and 24 with p-methoxybenzaldehyde (22) and 4-[(t-butyldimethylsilyl)oxy]benzaldehyde (26). Attempts at selective saponification of the resultant diesters yielded isoprenostodione (3a) bearing the ester functionality at the C-3 position of the indole ring. (C) 2013 Elsevier Ltd. All rights reserved.