5-methoxy-7-{2-[4-methoxymethoxy-2-(3-methylbut-2-enyl)-1H-indol-6-yl]vinyl}-1,1,4a-trimethyl-(2R,4aR,9aR)-2,3,4,4a,9,9a-hexahydro-1H-xanthen-2-ol | 1453472-34-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5-methoxy-7-{2-[4-methoxymethoxy-2-(3-methylbut-2-enyl)-1H-indol-6-yl]vinyl}-1,1,4a-trimethyl-(2R,4aR,9aR)-2,3,4,4a,9,9a-hexahydro-1H-xanthen-2-ol
• CAS: 1453472-34-8
• 化学式: C₃₄H₄₃NO₅
• 分子量: 545.719
• InChiKey: FZXUQJDRRDBOOK-OTUXHVHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.33
• 重原子数：
  40.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  72.94
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-methoxy-7-{2-[4-methoxymethoxy-2-(3-methylbut-2-enyl)-1H-indol-6-yl]vinyl}-1,1,4a-trimethyl-(2R,4aR,9aR)-2,3,4,4a,9,9a-hexahydro-1H-xanthen-2-ol 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以68%的产率得到6-[2-(7-hydroxy-4-methoxy-8,8,10a-trimethyl-(5R,8aR,10aR)-5,7,8,8a,9,10a-hexahydro-6H-xanthen-2-yl)-vinyl]-2-(3-methylbut-2-enyl)-1H-indol-4-ol
  参考文献：
  名称：

  Synthesis of Indole Analogues of the Natural Schweinfurthins

  摘要：

  An interest in the schweinfurthins, natural stilbenes with significant antiproliferative activity, has prompted efforts to prepare a set of indole analogues. To approach the desired compounds through a Horner-Wadsworth-Emmons condensation, new indole derivatives bearing a phosphonomethyl substituent in the B-ring were required. The parent indole system with the necessary substitution pattern was obtained through Stobbe condensation and cyclization. A prenyl substituent was incorporated at the C3 position of a 4,6-disubstituted indole through a highly regioselective electrophilic aromatic substitution reaction, while metalation and alkylation provided the C2-prenylated indole. After introduction of the phosphonate group through classical reactions, the new indole phosphonates were found to undergo the desired condensation with nonracemic aldehydes representing the schweinfurthin left half. This approach provides facile access to new heteroaromatic analogues of the natural schweinfurthins and should be applicable to many other natural stilbenes as well.

  DOI：

  10.1021/jo4014244
• 作为产物：
  描述：

  [4-methoxymethoxy-2-(3-methylbut-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-6-yl]methanol 在 15-冠醚-5 、 sodium hydride 、 甲基磺酰氯 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 11.08h， 生成 5-methoxy-7-{2-[4-methoxymethoxy-2-(3-methylbut-2-enyl)-1H-indol-6-yl]vinyl}-1,1,4a-trimethyl-(2R,4aR,9aR)-2,3,4,4a,9,9a-hexahydro-1H-xanthen-2-ol
  参考文献：
  名称：

  Synthesis of Indole Analogues of the Natural Schweinfurthins

  摘要：

  An interest in the schweinfurthins, natural stilbenes with significant antiproliferative activity, has prompted efforts to prepare a set of indole analogues. To approach the desired compounds through a Horner-Wadsworth-Emmons condensation, new indole derivatives bearing a phosphonomethyl substituent in the B-ring were required. The parent indole system with the necessary substitution pattern was obtained through Stobbe condensation and cyclization. A prenyl substituent was incorporated at the C3 position of a 4,6-disubstituted indole through a highly regioselective electrophilic aromatic substitution reaction, while metalation and alkylation provided the C2-prenylated indole. After introduction of the phosphonate group through classical reactions, the new indole phosphonates were found to undergo the desired condensation with nonracemic aldehydes representing the schweinfurthin left half. This approach provides facile access to new heteroaromatic analogues of the natural schweinfurthins and should be applicable to many other natural stilbenes as well.

  DOI：

  10.1021/jo4014244