(2aR,4S)-1-Benzoyl-4-dipropylamino-1,2,2a,3,4,5-hexahydro-benzo[cd]indole-6-carboxylic acid amide | 136791-10-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2aR,4S)-1-Benzoyl-4-dipropylamino-1,2,2a,3,4,5-hexahydro-benzo[cd]indole-6-carboxylic acid amide
• 英文别名: (2aR,4S)-1-benzoyl-4-(dipropylamino)-2a,3,4,5-tetrahydro-2H-benzo[cd]indole-6-carboxamide
• CAS: 136791-10-1
• 化学式: C₂₅H₃₁N₃O₂
• 分子量: 405.54
• InChiKey: IMQSTBCMPGZEMY-OALUTQOASA-N

物化性质

• 沸点：
  550.4±50.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  66.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2aR,4S)-1-Benzoyl-4-dipropylamino-1,2,2a,3,4,5-hexahydro-benzo[cd]indole-6-carboxylic acid amide 在 manganese(IV) oxide 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 9.5h， 生成 (4R)-4-(二丙基氨基)-1,3,4,5-四氢苯并[cd]吲哚-6-甲酰胺
  参考文献：
  名称：

  Synthetic Studies toward the Partial Ergot Alkaloid LY228729, a Potent 5HT_1A Receptor Agonist

  摘要：

  Synthetic studies on LY228729 (3) afforded two innovative approaches for the construction of this class of partial ergoline 5HT(1a) receptor agonists. The first synthesis is based upon a diastereoselective epoxidation of racemic olefin 5, followed by ring opening and covalent resolution to furnish the key amino alcohol 8. Aziridination of amino alcohol 8, with subsequent tandem hydrogenolysis of the benzylic aziridine and auxiliary bonds, provided access to the optically active primary amine 13. A novel catalytic carboxamidation reaction installed the requisite side chain, Alternatively, the chiral pool was drawn upon for the single stereogenic center by virtue of L-tryptophan, albeit by a more circuitous route than expected. L-Tryptophan was differentially protected and reduced to the indoline diastereomers 26a,b which were separated by fractional crystallization. The two indoline diastereoisomers were independently cyclized by a Friedel-Crafts protocol, which under thermodynamic control afforded enantiomeric ketones 30a. The ketone was deoxygenated with a two-step reduction protocol to intersect the initial route and complete the second total synthesis. The two routes offer complementary access to this exciting class of partial ergot alkaloids.

  DOI：

  10.1021/jo971256z
• 作为产物：
  描述：

  在 palladium on activated charcoal sodium hydroxide 、 sodium tetrahydroborate 、 三氯化铝 、 草酰氯 、 氨 、 氢气 、 碘 、 碳酸氢钠 、 potassium carbonate 、 钯 、 过碘酸 、 三苯基膦 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， -10.0~100.0 ℃ 、310.27 kPa 条件下， 反应 81.5h， 生成 (2aR,4S)-1-Benzoyl-4-dipropylamino-1,2,2a,3,4,5-hexahydro-benzo[cd]indole-6-carboxylic acid amide
  参考文献：
  名称：

  Synthetic Studies toward the Partial Ergot Alkaloid LY228729, a Potent 5HT_1A Receptor Agonist

  摘要：

  Synthetic studies on LY228729 (3) afforded two innovative approaches for the construction of this class of partial ergoline 5HT(1a) receptor agonists. The first synthesis is based upon a diastereoselective epoxidation of racemic olefin 5, followed by ring opening and covalent resolution to furnish the key amino alcohol 8. Aziridination of amino alcohol 8, with subsequent tandem hydrogenolysis of the benzylic aziridine and auxiliary bonds, provided access to the optically active primary amine 13. A novel catalytic carboxamidation reaction installed the requisite side chain, Alternatively, the chiral pool was drawn upon for the single stereogenic center by virtue of L-tryptophan, albeit by a more circuitous route than expected. L-Tryptophan was differentially protected and reduced to the indoline diastereomers 26a,b which were separated by fractional crystallization. The two indoline diastereoisomers were independently cyclized by a Friedel-Crafts protocol, which under thermodynamic control afforded enantiomeric ketones 30a. The ketone was deoxygenated with a two-step reduction protocol to intersect the initial route and complete the second total synthesis. The two routes offer complementary access to this exciting class of partial ergot alkaloids.

  DOI：

  10.1021/jo971256z