(4-methoxymethoxy-1-methoxymethyl-1H-indol-6-ylmethyl)phosphonic acid diethyl ester | 1453472-10-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (4-methoxymethoxy-1-methoxymethyl-1H-indol-6-ylmethyl)phosphonic acid diethyl ester
• CAS: 1453472-10-0
• 化学式: C₁₇H₂₆NO₆P
• 分子量: 371.37
• InChiKey: LFANVYAQNRQHNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  25.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  68.15
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (4-methoxymethoxy-1-methoxymethyl-1H-indol-6-ylmethyl)phosphonic acid diethyl ester 在 15-冠醚-5 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 mineral oil 为溶剂， 生成 7-[2-(4-hydroxy-1-methoxymethyl-1H-indol-6-yl)vinyl]-1,1,4a-trimethyl-(2R,4aR,9aR)-2,3,4,4a,9,9a-hexahydro-1H-xanthene-2,5-diol
  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-acetoxy-1H-indole-6-carboxylic acid ethyl ester 在 lithium aluminium tetrahydride 、 sodium hydride 、 potassium carbonate 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 、 mineral oil 为溶剂， 反应 4.33h， 生成 (4-methoxymethoxy-1-methoxymethyl-1H-indol-6-ylmethyl)phosphonic acid diethyl ester
  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