3-[(1R,2R,3R,6S)-6-isopropenyl-3-methyl-2-(methoxycarbonyl)amino-3-vinylcyclohexyl]-1-tosyl-1H-indole | 634599-58-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-[(1R,2R,3R,6S)-6-isopropenyl-3-methyl-2-(methoxycarbonyl)amino-3-vinylcyclohexyl]-1-tosyl-1H-indole
• 英文别名: methyl N-[(1R,2R,5R,6R)-2-ethenyl-2-methyl-6-[1-(4-methylphenyl)sulfonylindol-3-yl]-5-prop-1-en-2-ylcyclohexyl]carbamate
• CAS: 634599-58-9
• 化学式: C₂₉H₃₄N₂O₄S
• 分子量: 506.666
• InChiKey: DFZWOCDATQZKOR-ARGZUQHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  85.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[(1R,2R,3R,6S)-6-isopropenyl-3-methyl-2-(methoxycarbonyl)amino-3-vinylcyclohexyl]-1-tosyl-1H-indole 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 (+)-hapalindole Q
  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
• 作为产物：
  描述：

  甲基三苯基碘化膦 、 3-[(1R,2R,3R,6S)-6-acetyl-3-methyl-2-(methoxycarbonyl)amino-3-vinylcyclohexyl]-1-tosyl-1H-indole 在 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以20 mg的产率得到3-[(1R,2R,3R,6S)-6-isopropenyl-3-methyl-2-(methoxycarbonyl)amino-3-vinylcyclohexyl]-1-tosyl-1H-indole
  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