toluene-4-sulfonic acid 5-methoxy-7-[2-(4-methoxymethoxy-1H-indol-6-yl)vinyl]-1,1,4a-trimethyl-(2R,4aR,9aR)-2,3,4,4a,9,9a-hexahydro-1H-xanthen-2-yl ester | 1453472-22-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: toluene-4-sulfonic acid 5-methoxy-7-[2-(4-methoxymethoxy-1H-indol-6-yl)vinyl]-1,1,4a-trimethyl-(2R,4aR,9aR)-2,3,4,4a,9,9a-hexahydro-1H-xanthen-2-yl ester
• CAS: 1453472-22-4
• 化学式: C₃₆H₄₁NO₇S
• 分子量: 631.79
• InChiKey: LNSPCAZPCVYGPE-KVXOBKLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.54
• 重原子数：
  45.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  96.08
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  toluene-4-sulfonic acid 5-methoxy-7-[2-(4-methoxymethoxy-1H-indol-6-yl)vinyl]-1,1,4a-trimethyl-(2R,4aR,9aR)-2,3,4,4a,9,9a-hexahydro-1H-xanthen-2-yl ester 在 盐酸 、 lithium aluminium tetrahydride 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 8.5h， 生成 6-[2-(7-hydroxy-4-methoxy-8,8,10a-trimethyl-(5R,8aR,10aR)-5,7,8,8a,9a,10a-hexahydro-6H-xanthen-2-yl)vinyl]-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-acetoxy-1H-indole-6-carboxylic acid ethyl ester 在 咪唑 、 正丁基锂 、 15-冠醚-5 、 四丁基氟化铵 、 sodium hydride 、 二异丁基氢化铝 、 potassium carbonate 、 甲基磺酰氯 、 三乙胺 、 N,N-二异丙基乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 mineral oil 为溶剂， 反应 11.83h， 生成 toluene-4-sulfonic acid 5-methoxy-7-[2-(4-methoxymethoxy-1H-indol-6-yl)vinyl]-1,1,4a-trimethyl-(2R,4aR,9aR)-2,3,4,4a,9,9a-hexahydro-1H-xanthen-2-yl 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