3-[4,6-dimethyl-3-formylbicyclo[2.2.2]oct-5-en-2-yl]-1-tosyl-1H-indole

• 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: 3-[4,6-dimethyl-3-formylbicyclo[2.2.2]oct-5-en-2-yl]-1-tosyl-1H-indole
• 英文别名: 1,5-Dimethyl-3-[1-(4-methylphenyl)sulfonylindol-3-yl]bicyclo[2.2.2]oct-5-ene-2-carbaldehyde
• 化学式: C₂₆H₂₇NO₃S
• 分子量: 433.571
• InChiKey: RTNOUYQVJFQGEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  64.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[4,6-dimethyl-3-formylbicyclo[2.2.2]oct-5-en-2-yl]-1-tosyl-1H-indole 在 sodium chlorite 、 sodium dihydrogenphosphate 作用下， 以 叔丁醇 为溶剂， 反应 1.0h， 生成 (1R,2R,3S,4R)-1,5-Dimethyl-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-bicyclo[2.2.2]oct-5-ene-2-carboxylic acid 、 {(1S,2R,3R,4S)-1,5-Dimethyl-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-bicyclo[2.2.2]oct-5-en-2-yl}-carbamic acid
  参考文献：
  名称：

  The Total Synthesis of (+)-Hapalindole Q by an Organomediated Diels−Alder Reaction

  摘要：

  The total synthesis of (+)-hapalindole Q has been achieved. The key step is a Diels-Alder reaction mediated by MacMillan's organocatalyst to provide the critical intermediate with high enantioselectivity (93% ee). This step establishes the proper arrangement of the required four contiguous stereocenters, including the quaternary center, and represents the first successful application of an enantioselective organomediated Diels-Alder reaction in total synthesis.

  DOI：

  10.1021/ja036191y